Exhibit 10.1

LOAN AND SECURITY AGREEMENT

This LOAN AND SECURITY AGREEMENT (this "Agreement") dated as of December 28, 2001, between SILICON VALLEY BANK, a California chartered bank, with its principal place of business at 3003 Tasman Drive, Santa Clara, California 95054 and with a loan production office located at One Newton Executive Park, Suite 200, 2221 Washington Street, Newton, Massachusetts 02462, doing business under the name "Silicon Valley East" ("Bank") and BOTTOMLINE TECHNOLOGIES (de), INC., a Delaware corporation with offices at 155 Fleet Street, Portsmouth, New Hampshire 03801 ("Borrower"), provides the terms on which Bank shall lend to Borrower and Borrower shall repay Bank. The parties agree as follows:

1 ACCOUNTING AND OTHER TERMS

Accounting terms not defined in this Agreement shall be construed following GAAP. Calculations and determinations must be made following GAAP. The term "financial statements" includes the notes and schedules. The terms "including" and "includes" always mean "including (or includes) without limitation," in this or any Loan Document. Capitalized terms in this Agreement shall have the meanings set forth in Section 13.

2 LOAN AND TERMS OF PAYMENT

2.1 Promise to Pay. Borrower hereby unconditionally promises to pay Bank the unpaid principal amount of all Credit Extensions and interest on the unpaid principal amount of the Credit Extensions as and when due in accordance with this Agreement.

2.1.1 Revolving Advances.

(a) Bank shall make Advances not exceeding (i) the Committed Revolving Line or the Borrowing Base, whichever is less, minus (ii) the amount of all outstanding Letters of Credit (including drawn but unreimbursed Letters of Credit), minus (iii) the aggregate outstanding Advances hereunder. Amounts borrowed under this Section may be repaid and reborrowed during the term of this Agreement.

(b) To obtain an Advance, Borrower must notify Bank by facsimile or telephone by 3:00 p.m. Eastern time on the Business Day the Advance is to be made. If such notification is by telephone, Borrower must promptly confirm the notification by delivering to Bank a completed Payment/Advance Form in the form attached as Exhibit B. Bank shall credit Advances to Borrower's deposit account. Bank may make Advances under this Agreement based on instructions from a Responsible Officer or his or her designee. Bank may rely on any telephone notice given by a person whom Bank reasonably believes is a Responsible Officer or designee. Borrower shall indemnify Bank for any loss Bank suffers due to such reliance.

(c) The Committed Revolving Line terminates on the Revolving Maturity Date, when the principal amount of all Advances and the unpaid interest thereon, shall be immediately payable.

2.1.2 Letters of Credit.

(a) Bank shall issue or have issued Letters of Credit for Borrower's account not exceeding (i) the lesser of the Committed Revolving Line or the Borrowing Base minus (ii) the outstanding principal balance of any Advances, minus (iii) the amount of all Letters of Credit (including drawn but unreimbursed Letters of Credit), plus an amount equal to any Letter of Credit Reserves. The face amount of outstanding Letters of Credit (including drawn but unreimbursed Letters of Credit and any Letter of Credit Reserve) may not exceed $2,000,000.00. Each Letter of Credit shall have an expiry date no later than 180 days after the Revolving Maturity Date provided Borrower's Letter of Credit reimbursement obligation shall be secured by cash on terms acceptable to Bank on and after (i) the Revolving Maturity Date if the term of this Agreement is not extended by Bank, or (ii) the occurrence of an Event of Default hereunder. All Letters of Credit shall be, in form and substance, acceptable to Bank in its sole discretion and shall be subject to the terms and conditions of Bank's form of standard Application and Letter of

Credit Agreement. Borrower agrees to execute any further documentation in connection with the Letters of Credit as Bank may reasonably request.

(b) The obligation of Borrower to immediately reimburse Bank for drawings made under Letters of Credit shall be absolute, unconditional and irrevocable, and shall be performed strictly in accordance with the terms of this Agreement and such Letters of Credit, under all circumstances whatsoever. Borrower shall indemnify, defend, protect, and hold Bank harmless from any loss, cost, expense or liability, including, without limitation, reasonable attorneys' fees, arising out of or in connection with any Letters of Credit.

(c) Borrower may request that Bank issue a Letter of Credit payable in a currency other than United States Dollars. If a demand for payment is made under any such Letter of Credit, Bank shall treat such demand as an Advance to Borrower of the equivalent of the amount thereof (plus cable charges) in United States currency at the then prevailing rate of exchange in San Francisco, California, for sales of that other currency for cable transfer to the country of which it is the currency.

(d) Upon the issuance of any letter of credit payable in a currency other than United States Dollars, Bank shall create a reserve (the "Letter of Credit Reserve") under the Committed Revolving Line for letters of credit against fluctuations in currency exchange rates, in an amount equal to ten percent (10%) of the face amount of such letter of credit. The amount of such reserve may be amended by Bank from time to time to account for fluctuations in the exchange rate. The availability of funds under the Committed Revolving Line shall be reduced by the amount of such reserve for so long as such letter of credit remains outstanding.

2.2 Overadvances. If Borrower's Obligations under Section 2.1.1 and 2.1.2 exceed the lesser of either (i) the Committed Revolving Line or (ii) the Borrowing Base, Borrower must immediately pay in cash to Bank the excess.

2.3 Interest Rate; Payments.

(a) Interest Rate. Advances accrue interest on the outstanding principal balance at a per annum rate equal to the aggregate of the Bank's Prime Rate, and one-half of one percent (0.50%). After an Event of Default, Obligations shall bear interest at four percent (4.0%) above the rate effective immediately before the Event of Default. The interest rate shall increase or decrease when the Prime Rate changes. Interest is computed on the basis of a 360 day year for the actual number of days elapsed.

(b) Payments. Interest is payable on the first of each month. Bank may debit any of Borrower's deposit accounts (unless prohibited by law) including Account Number __________ for principal and interest payments or any amounts Borrower owes Bank. Bank shall promptly notify Borrower when it debits Borrower's accounts. These debits are not a set-off. Payments received after 12:00 noon Eastern time are considered received at the opening of business on the next Business Day. When a payment is due on a day that is not a Business Day, the payment is due the next Business Day and additional fees or interest, as applicable, shall continue to accrue.

2.4 Fees. Borrower shall pay to Bank:

(a) Facility Fee. A fully earned, non-refundable facility fee of $25,000.00 due on the Closing Date;

(b) Unused Facility Fee. As compensation for Bank's maintenance of sufficient funds available for such purpose, Bank shall have earned a Unused Facility Fee (so referred to herein), which fee shall be paid in full quarterly in arrears, in an amount equal to (i) 0.50% of the unused portion of the available proceeds of the Committed Revolving Line minus that portion of the Committed Revolving Line which is available to be used to issue Letters of Credit and (ii) 0.40% of the unused portion of the available proceeds of the Committed Revolving Line which are available to be used to issue Letters of Credit, which shall be calculated based on the average daily

availability during each such quarter. The Borrower shall not be entitled to any credit, rebate or repayment of any Unused Facility Fee previously earned by the Bank pursuant to this Section notwithstanding any termination of the within Agreement, or suspension or termination of the Bank's obligation to make loans and advances hereunder; and

(c) Bank Expenses. All Bank Expenses (including reasonable attorneys' fees and expenses incurred through and after the Closing Date) when due.

3 CONDITIONS OF LOANS

3.1 Conditions Precedent to Initial Credit Extension. The obligation of Bank to make the initial Credit Extension is subject to the condition precedent that Bank shall have received, in form and substance satisfactory to Bank, the following:

(a) this Agreement;

(b) a certificate of the Secretary of Borrower with respect to articles, bylaws, incumbency and resolutions authorizing the execution and delivery of this Agreement;

(c) Negative Pledge Agreement covering Intellectual Property;

(d) landlord's waiver;

(e) a legal opinion of Borrower's counsel, in form and substance acceptable to Bank;

(f) financing statements;

(g) Account Control Agreement/ Investment Account Control Agreement

(h) insurance certificate;

(i) payment of the fees and Bank Expenses then due specified in
Section 2.4 hereof;

(j) Certificate of Foreign Qualification (if applicable);

(k) Certificate of Good Standing/Legal Existence; and

(l) such other documents, and completion of such other matters, as Bank may reasonably deem necessary or appropriate.

3.2 Conditions Precedent to all Credit Extensions. Bank's obligations to make each Credit Extension, including the initial Credit Extension, is subject to the following:

(a) timely receipt of any Payment/Advance Form; and

(b) the representations and warranties in Section 5 shall be materially true on the date of the Payment/Advance Form and on the effective date of each Credit Extension and no Event of Default shall have occurred and be continuing, or result from the Credit Extension. Each Credit Extension is Borrower's representation and warranty on that date that the representations and warranties in Section 5 remain true.

4 CREATION OF SECURITY INTEREST

4.1 Grant of Security Interest. Borrower hereby grants Bank, to secure the payment and performance in full of all of the Obligations and the performance of each of Borrower's duties under the Loan Documents, a continuing security interest in the Collateral, wherever located, whether now owned or hereafter acquired or arising, and all proceeds and products thereof. Borrower warrants and represents that the security interest granted herein shall be a first priority security interest in the Collateral. The Collateral may also be subject to Permitted Liens. Borrower agrees that Bank may file (with the UCC Financing Statements to be filed hereunder) a notice that any disposition of the Collateral in violation of this Agreement, by either the Borrower or any other Person, shall be deemed to violate the rights of the Bank under the Code. If the Borrower shall at any time have knowledge that it has acquired a material commercial tort claim, Borrower shall use best efforts to promptly notify Bank in a writing signed by Borrower of the brief details thereof and grant to Bank in such writing a security interest therein and in the proceeds thereof, all upon the terms of this Agreement, with such writing to be in form and substance satisfactory to Bank. If the Agreement is terminated, Bank's lien and security interest in the Collateral shall continue until Borrower fully satisfies its Obligations.

5 REPRESENTATIONS AND WARRANTIES

Borrower represents and warrants as follows:

5.1 Due Organization and Authorization. Borrower is duly existing and in good standing in its state of formation and qualified and licensed to do business in, and in good standing in, any state in which the conduct of its business or its ownership of property requires that it be qualified, except where the failure to do so could not reasonably be expected to cause a Material Adverse Change. The Borrower has previously delivered to the Bank a certificate signed by the Borrower and entitled "Perfection Certificate". The Borrower represents and warrants to the Bank that: (a) the Borrower's exact legal name is that indicated on the Perfection Certificate and on the signature page hereof; and (b) the Borrower is an organization of the type, and is organized in the jurisdiction, set forth in the Perfection Certificate; and (c) the Perfection Certificate accurately sets forth the Borrower's organizational identification number or accurately states that the Borrower has none; and (d) the Perfection Certificate accurately sets forth the Borrower's place of business, or, if more than one, its chief executive office as well as the Borrower's mailing address if different, and (e) all other information set forth on the Perfection Certificate pertaining to the Borrower is accurate and complete. If the Borrower does not now have an organizational identification number, but later obtains it, Borrower shall forthwith notify the Bank or such organizational identification number.

The execution, delivery and performance of the Loan Documents have been duly authorized, and do not conflict with Borrower's organizational documents, nor constitute an event of default under any material agreement by which Borrower is bound. Borrower is not in default under any agreement to which or by which it is bound in which the default could cause a Material Adverse Change.

5.2 Collateral. Borrower has good title to the Collateral, free of Liens except Permitted Liens. Borrower has no other deposit account, other than the deposit accounts with Bank and deposit accounts described in the Perfection Certificate delivered to the Bank in connection herewith. The Accounts are bona fide, existing obligations, and the service or property has been performed or delivered to the account debtor or its agent for immediate shipment to and unconditional acceptance by the account debtor. The Collateral is not in the possession of any third party bailee (such as a warehouse) except (i) as listed in the Perfection Certificate or (ii) Inventory stored at Borrower's vendor's locations in the ordinary course of business in amounts consistent with past practices. In the event that Borrower, after the date hereof, intends to store or otherwise deliver any portion of the Collateral to a bailee (other than (i) as listed in the Perfection Certificate or (ii) Inventory stored at Borrower's vendor's locations in the ordinary course of business in amounts consistent with past practices) then Borrower will first receive the written consent of Bank and such bailee must acknowledge in writing that the bailee is holding such Collateral for the benefit of Bank. Borrower has no knowledge of any actual or imminent Insolvency Proceeding of any account debtor whose accounts are an Eligible Account in any Borrowing Base Certificate. All Inventory is in all material respects of good and marketable quality, free from material defects.

5.3 Litigation. Except as shown in the Schedule, there are no actions or proceedings pending or, to the knowledge of Borrower's Responsible Officers, threatened by or against Borrower in which an adverse decision could reasonably be expected to cause a Material Adverse Change.

5.4 No Material Adverse Change in Financial Statements. All consolidated financial statements for Borrower delivered to Bank fairly present in all material respects Borrower's consolidated financial condition and Borrower's consolidated results of operations as of the date of such financial statements. There has not been any material deterioration in Borrower's consolidated financial condition since the date of the most recent financial statements submitted to Bank.

5.5 Solvency. Borrower is able to pay its debts (including trade debts) as they mature.

5.6 Regulatory Compliance. Borrower is not an "investment company" or a company "controlled" by an "investment company" under the Investment Company Act. Borrower is not engaged as one of its important activities in extending credit for margin stock (under Regulations T and U of the Federal Reserve Board of Governors). Borrower has complied in all material respects with the Federal Fair Labor Standards Act. Borrower has not violated any laws, ordinances or rules, the violation of which could reasonably be expected to cause a Material Adverse Change. None of Borrower's properties or assets has been used by Borrower, to the best of Borrower's knowledge, by previous Persons, in disposing, producing, storing, treating, or transporting any hazardous substance other than legally. Borrower has timely filed all required tax returns and paid, or made adequate provision to pay, all material taxes, except those being contested in good faith with adequate reserves under GAAP. Borrower has obtained all consents, approvals and authorizations of, made all declarations or filings with, and given all notices to, all government authorities that are necessary to continue its business as currently conducted except where the failure to make such declarations, notices or filings would not reasonably be expected to cause a Material Adverse Change.

5.7 Subsidiaries. Borrower does not own any stock, partnership interest or other equity securities except for Permitted Investments.

5.8 Full Disclosure. No written representation, warranty or other statement of Borrower in any certificate or written statement given to Bank contains any untrue statement of a material fact when made or omits to state a material fact necessary to make the statements contained in the certificates or statements not misleading when made.

6 AFFIRMATIVE COVENANTS

Until Borrower satisfies all obligations under this Agreement and Bank commitment to lend hereunder is terminated, Borrower shall do all of the following:

6.1 Government Compliance. Borrower shall maintain its legal existence and good standing in its jurisdiction of formation and maintain qualification in each jurisdiction in which the failure to so qualify would reasonably be expected to have a material adverse effect on Borrower's business or operations. Borrower shall comply with all laws, ordinances and regulations to which it is subject, noncompliance with which would reasonably be expected to cause a Material Adverse Change.

6.2 Financial Statements, Reports, Certificates.

(a) Borrower shall deliver to Bank: (i) as soon as available, but no later than thirty(30) days after the last day of each month, a company prepared consolidated and consolidating balance sheet and income statement covering Borrower's consolidated operations during the period certified by a Responsible Officer and in a form acceptable to Bank; (ii) as soon as available, but no later than ninety (90) days after the last day of Borrower's fiscal year, audited consolidated financial statements prepared under GAAP, consistently applied, together with an

unqualified opinion on the financial statements from an independent certified public accounting firm reasonably acceptable to Bank; (iii) within ten (10) days of filing, copies of all statements, reports and notices made available to Borrower's security holders or to any holders of Subordinated Debt and all reports on Form 10-K, 10-Q and 8-K filed with the Securities and Exchange Commission; (iv) a prompt report of any legal actions pending or threatened against Borrower that would reasonably be expect to result in damages or costs to Borrower of Three Hundred Thousand Dollars ($300,000.00) or more; and (v) budgets, sales projections, operating plans or other financial information reasonably requested by Bank.

(b) Within thirty (30) days after the last day of each month, Borrower shall deliver to Bank a Borrowing Base Certificate signed by a Responsible Officer in the form of Exhibit C, with aged listings of accounts receivable (by invoice date).

(c) Within thirty (30) days after the last day of each month, Borrower shall deliver to Bank with the monthly financial statements a Compliance Certificate signed by a Responsible Officer in the form of Exhibit D.

(d) Borrower shall allow Bank to audit Borrower's Collateral at Borrower's expense. Such audits shall be conducted no more often than once every twelve (12) months unless an Event of Default has occurred and is continuing.

6.3 Inventory; Returns. Borrower shall keep all Inventory in good and marketable condition, free from material defects. Returns and allowances between Borrower and its account debtors shall follow Borrower's customary practices as they exist at the Closing Date. Borrower must promptly notify Bank of all returns, recoveries, disputes and claims that involve more than Two Hundred Thousand Dollars ($200,000.00).

6.4 Taxes. Borrower shall make timely payment of all material federal, state, and local taxes or assessments (other than taxes and assessments which Borrower is contesting in good faith, with adequate reserves maintained in accordance with GAAP) and will deliver to Bank, on demand, appropriate certificates attesting to such payments.

6.5 Insurance. Borrower shall keep its business and the Collateral insured for risks and in amounts, standard for Borrower's industry, and as Bank may reasonably request in Bank's reasonable discretion. Insurance policies shall be in a form, with companies, and in amounts that are reasonably satisfactory to Bank. All property policies shall have a lender's loss payable endorsement showing Bank as an additional loss payee and all liability policies shall show the Bank as an additional insured and all policies shall provide that the insurer must give Bank at least twenty (20) days notice before canceling its policy. At Bank's request, Borrower shall deliver certified copies of policies and evidence of all premium payments. Proceeds payable under any policy shall, at Bank's option, be payable to Bank on account of the Obligations. Notwithstanding the foregoing, so long as no Event of Default has occurred and is continuing, Borrower shall have the option of applying the proceeds of any casualty policy up to $100,000.00, in the aggregate toward the replacement or repair of destroyed or damaged property; provided that (i) any such replaced or repaired property (a) shall be of equal or like value as the replaced or repaired Collateral and (b) shall be deemed Collateral in which Bank has been granted a first priority security interest and (ii) after the occurrence and during the continuation of an Event of Default all proceeds payable under such casualty policy shall, at the option of the Bank, be payable to Bank on account of the Obligations. If Borrower fails to obtain insurance as required under
Section 6.5 or to pay any amount or furnish any required proof of payment to third persons and the Bank, Bank may make all or part of such payment or obtain such insurance policies required in Section 6.5, and take any action under the policies Bank deems prudent.

6.6 Primary Accounts. In order to permit Bank to monitor Borrower's financial performance and condition, Borrower shall maintain its primary depository and operating accounts and securities accounts with Bank and a majority of the Borrower's cash or securities in excess of that amount used for Borrower's operations shall be maintained or administered through the Bank. Borrower shall identify to Bank, in writing, of any bank or securities account opened by Borrower with any institution other than Bank. In addition, for each such account that the

Borrower at any time opens or maintains, Borrower shall, at the Bank's request and option, pursuant to an agreement in form and substance acceptable to the Bank, cause the depositary bank or securities intermediary to agree that such account is the collateral of the Bank pursuant to the terms hereunder. The provisions of this paragraph shall not apply to deposit accounts exclusively used for payroll, payroll taxes and other employee wage and benefit payments to or for the benefit of the Borrower's employees.

6.7 Financial Covenants.

Borrower shall maintain at all times, to be tested as of the last day of each month, unless otherwise noted:

(a) Adjusted Quick Ratio. Borrower shall maintain a ratio of Quick Assets to Current Liabilities minus Deferred Revenue of at least 2.0 to
1.0. For the purposes hereof, Quick Assets, Current Liabilities and Deferred Revenue shall relate only to Borrower's operations (i.e., exclude foreign operations of subsidiaries).

(b) Maximum Net Loss/Minimum Net Profit. For any month Borrower fails to maintain at least $7,000,000.00 in cash on deposit with the Bank, Borrower (together with its subsidiaries on a consolidated basis) shall have (i) Net Loss (based on the prior rolling three month period) not to exceed (A) $2,250,000 for the month ending October 31, 2001, (B) $2,000,000 for the month ending November 30, 2001, (C)$1,700,000 for the month ending December 31, 2001, (D) $1,600,000 for the month ending January 31, 2002, (E) $1,250,000 for the month ending February 28, 2002, (F) $800,000 for the month ending March 31, 2002, (G) $625,000 for the months ending April 30, 2002, May 31, 2002 and June 30, 2002; and (ii) net profit (based on the prior rolling three month period) of One Dollar ($1.00), for each month thereafter.

6.8 Further Assurances. Borrower shall execute any further instruments and take further action as Bank reasonably requests to perfect or continue Bank's security interest in the Collateral or to effect the purposes of this Agreement.

7 NEGATIVE COVENANTS

Until Borrower satisfies all obligations under this Agreement and Bank's commitment to lend hereunder is terminated, Borrower shall not do any of the following without the Bank's prior written consent.

7.1 Dispositions. Convey, sell, lease, transfer or otherwise dispose of (collectively a "Transfer"), all or any part of its business or property, except for Transfers (i) of Inventory in the ordinary course of business; (ii) of non-exclusive licenses and similar arrangements for the use of the property of Borrower in the ordinary course of business; or (iii) of worn-out or obsolete Equipment.

7.2 Changes in Business, Ownership, Management or Business Locations. Engage in any business other than the businesses currently engaged in by Borrower or have a material change in its ownership (other than by the sale of Borrower's equity securities in a public or private offering so long as Borrower identifies to Bank the investors prior to the closing of the investment and within thirty (30) days after such investment, Bank and Borrower shall agree to revised financial performance covenants and shall amend this Agreement accordingly) or if any of (i) Daniel McGurl or (ii) Joseph Mullen, or (iii) Robert Eberle cease to be employees or directors of Borrower and replacements satisfactory to Bank are not made within thirty (30) days. Borrower shall not, without at least thirty (30) days prior written notice to Bank: (i) relocate its chief executive office, or add any new offices or business locations (unless such new offices or business locations contain less than Fifty Thousand Dollars ($50,000.00) in Borrower's assets or property), or (ii) change its jurisdiction of organization, or (iii) change its organizational structure or type, or (iv) change its legal name, or (v) change any organizational number (if any) assigned by its jurisdiction of organization.

7.3 Mergers or Acquisitions. Merge or consolidate with any other Person, or acquire all or substantially all of the capital stock or property of another Person, unless: (i) there is no Event of Default hereunder, (ii) that such merger, consolidation or acquisition will not result, on a post merger/acquisition basis, in the breach of any of the covenants, terms and conditions hereunder, (iii) that such acquired, merged or consolidated Person is in the same or similar line of business as Borrower, (iv) Borrower is the surviving legal entity, (v) Borrower incurs no additional indebtedness other than Permitted Indebtedness and (vi) within thirty (30) days after such merger, consolidation or acquisition, Bank and Borrower shall agree to revised financial performance covenants and shall amend this Agreement accordingly.

7.4 Indebtedness. Create, incur, assume, or be liable for any Indebtedness, other than Permitted Indebtedness.

7.5 Encumbrance. Create, incur, or allow any Lien on any of its property, or assign or convey any right to receive income, including the sale of any Accounts, except for Permitted Liens, or permit any Collateral not to be subject to the first priority security interest granted herein. The Collateral may also be subject to Permitted Liens.

7.6 Distributions; Investments. (i) Directly or indirectly acquire or own any Person, or make any Investment in any Person, other than Permitted Investments; or (ii) pay any dividends or make any distribution or payment or redeem, retire or purchase any capital stock (except pursuant to Borrower's existing $3,000,000 stock buy back program).

7.7 Transactions with Affiliates. Directly or indirectly enter or permit any material transaction with any Affiliate, except transactions that are in the ordinary course of Borrower's business, upon fair and reasonable terms that are no less favorable to Borrower than would be obtained in an arm's length transaction with a non-affiliated Person.

7.8 Subordinated Debt. Make or permit any payment on any Subordinated Debt, except under the terms of the Subordinated Debt, or amend any provision in any document relating to the Subordinated Debt, without Bank's prior written consent.

7.9 Compliance. Become an "investment company" or a company controlled by an "investment company", under the Investment Company Act of 1940 or undertake as one of its important activities extending credit to purchase or carry margin stock, or use the proceeds of any Credit Extension for that purpose; fail to meet the minimum funding requirements of ERISA, permit a Reportable Event or Prohibited Transaction, as defined in ERISA, to occur; fail to comply with the Federal Fair Labor Standards Act or violate any other law or regulation, if the violation could reasonably be expected to have a material adverse effect on Borrower's business or operations or would reasonably be expected to cause a Material Adverse Change.

8 EVENTS OF DEFAULT

Any one of the following is an Event of Default:

8.1 Payment Default. Borrower fails to pay any of the Obligations within three (3) days after their due date. During the additional period the failure to cure the default is not an Event of Default (but no Credit Extension shall be made during the cure period);

8.2 Covenant Default. Borrower does not perform any obligation in Section 6 or violates any covenant in Section 7 or does not perform or observe any other material term, condition or covenant in this Agreement, any Loan Documents, or in any agreement between Borrower and Bank and as to any default under a term, condition or covenant that can be cured, has not cured the default within ten
(10) days after it occurs, or if the default cannot be cured within ten (10) days or cannot be cured after Borrower's attempts in the ten (10) day period, and the default may be cured within a reasonable time, then Borrower shall have additional time, (of not more than

thirty (30) days) to attempt to cure the default. Grace periods provided under this section shall not apply, among other things, to financial covenants or any other covenants that are required to be satisfied, completed or tested by a date certain. During the additional period the failure to cure the default is not an Event of Default (but no Credit Extensions shall be made during the cure period);

8.3 Material Adverse Change. A Material Adverse Change occurs;

8.4 Attachment. (i) Any material portion of Borrower's assets is attached, seized, levied on, or comes into possession of a trustee or receiver and the attachment, seizure or levy is not removed in ten (10) days; (ii) the service of process upon the Borrower seeking to attach, by trustee or similar process any material amount of funds of the Borrower on deposit with the Bank; (iii) Borrower is enjoined, restrained, or prevented by court order from conducting a material part of its business; (iv) a judgment or other claim becomes a Lien on a material portion of Borrower's assets; or (v) a notice of lien, levy, or assessment is filed against any of Borrower's assets by any government agency and not paid within ten (10) days after Borrower receives notice. These are not Events of Default if stayed or if a bond is posted pending contest by Borrower (but no Credit Extensions shall be made during the cure period);

8.5 Insolvency. (i) Borrower becomes insolvent; (ii) Borrower begins an Insolvency Proceeding; or (iii) an Insolvency Proceeding is begun against Borrower and not dismissed or stayed within forty-five (45) days (but no Credit Extensions shall be made before any Insolvency Proceeding is dismissed);

8.6 Other Agreements. If there is a default in any agreement to which Borrower is a party with a third party or parties resulting in a right by such third party or parties, whether or not exercised, to accelerate the maturity of any Indebtedness in an amount in excess of One Hundred Thousand Dollars ($100,000) or that is reasonably likely to result in a Material Adverse Change;

8.7 Judgments. If a judgment or judgments for the payment of money in an amount, individually or in the aggregate, of at least Two Hundred Thousand Dollars ($200,000) shall be rendered against Borrower and shall remain unsatisfied and unstayed for a period of ten (10) days (provided that no Credit Extensions will be made prior to the satisfaction or stay of such judgment);

8.8 Revised Covenants. If Borrower and Bank do not agree to revised financial performance covenants, if such revision is required in accordance with
Section 7.2 or Section 7.3 hereof, forty-five (45) days after the expiration of the time period to agree on same set forth in Section 7.2 or Section 7.3 hereof; or

8.9 Misrepresentations. If Borrower or any Person acting for Borrower makes any material misrepresentation or material misstatement now or later in any warranty or representation in this Agreement or in any writing delivered to Bank or to induce Bank to enter this Agreement or any Loan Document.

9 BANK'S RIGHTS AND REMEDIES

9.1 Rights and Remedies. When an Event of Default occurs and continues Bank may, without notice or demand, do any or all of the following:

(a) Declare all Obligations immediately due and payable (but if an Event of Default described in Section 8.5 occurs all Obligations are immediately due and payable without any action by Bank);

(b) Stop advancing money or extending credit for Borrower's benefit under this Agreement or under any other agreement between Borrower and Bank;

(c) Settle or adjust disputes and claims directly with account debtors for amounts, on terms and in any order that Bank considers advisable;

(d) Make any payments and do any acts it considers reasonably necessary to protect its security interest in the Collateral. Borrower shall assemble the Collateral if Bank requests and make it available as Bank designates. Subject to the rights of third parties, prohibitions or limitations in agreements with third parties, and applicable law, Bank may enter premises where the Collateral is located, take and maintain possession of any part of the Collateral, and pay, purchase, contest, or compromise any Lien which appears to be prior or superior to its security interest and pay all expenses incurred. Subject to the rights of third parties, prohibitions or limitations in agreements with third parties, and applicable law, Borrower grants Bank a license to enter and occupy any of its premises, without charge, to exercise any of Bank's rights or remedies;

(e) Apply to the Obligations any (i) balances and deposits of Borrower it holds, or (ii) any amount held by Bank owing to or for the credit or the account of Borrower;

(f) Ship, reclaim, recover, store, finish, maintain, repair, prepare for sale, advertise for sale, and sell the Collateral in accordance with the Code or other applicable law. Subject to the rights of third parties, prohibitions or limitations in agreements with third parties, and applicable law, Bank is granted a non-exclusive, royalty-free license or other right to use, without charge, Borrower's labels, patents, copyrights, mask works, rights of use of any name, trade secrets, trade names, trademarks, service marks, and advertising matter, or any similar property as it pertains to the Collateral, in completing production of, advertising for sale, and selling any Collateral and, in connection with Bank's exercise of its rights under this Section, Borrower's rights under all licenses and all franchise agreements inure to Bank's benefit, subject to the rights of third parties, prohibitions or limitations in agreements with third parties, and applicable law; and

(g) Otherwise dispose of the Collateral according to the Code.

9.2 Power of Attorney. Borrower hereby irrevocably appoints Bank as its lawful attorney-in-fact, to be effective upon the occurrence and during the continuance of an Event of Default, to: (i) endorse Borrower's name on any checks or other forms of payment or security; (ii) sign Borrower's name on any invoice or bill of lading for any Account or drafts against account debtors;
(iii) settle and adjust disputes and claims about the Accounts directly with account debtors, for amounts and on terms Bank determines reasonable; (iv) make, settle, and adjust all claims under Borrower's insurance policies; and (v) transfer the Collateral into the name of Bank or a third party as the Code permits. Borrower hereby appoints Bank as its lawful attorney-in-fact to sign Borrower's name on any documents necessary to perfect or continue the perfection of any security interest regardless of whether an Event of Default has occurred until all Obligations have been satisfied in full and Bank is under no further obligation to make Credit Extensions hereunder. Bank's foregoing appointment as Borrower's attorney in fact, and all of Bank's rights and powers, coupled with an interest, are irrevocable until all Obligations have been fully repaid and performed and Bank's obligation to provide Credit Extensions terminates.

9.3 Accounts Collection. In the event that an Event of Default occurs and is continuing, Bank may notify any Person owing Borrower money of Bank's security interest in the funds and verify and/or collect the amount of the Account. Any amounts received by Borrower shall, upon request by Bank, be held in trust by Borrower for Bank, and, if requested by Bank, Borrower shall immediately deliver such receipts to Bank in the form received from the account debtor, with proper endorsements for deposit.

9.4 Bank Expenses. All Bank Expenses are immediately due and payable, and shall bear interest at the then applicable rate and be secured by the Collateral. No payments by Bank shall be deemed an agreement to make similar payments in the future or Bank's waiver of any Event of Default.

9.5 Bank's Liability for Collateral. So long as the Bank complies with reasonable banking practices regarding the safekeeping of collateral, the Bank shall not be liable or responsible for: (a) the safekeeping of the Collateral;
(b) any loss or damage to the Collateral; (c) any diminution in the value of the Collateral; or (d) any act or default of any carrier, warehouseman, bailee, or other person. Except for the foregoing, Borrower bears all risk of loss, damage or destruction of the Collateral.

9.6 Remedies Cumulative. Bank's rights and remedies under this Agreement, the Loan Documents, and all other agreements are cumulative. Bank has all rights and remedies provided under the Code, by law, or in equity. Bank's exercise of one right or remedy is not an election, and Bank's waiver of any Event of Default is not a continuing waiver. Bank's delay is not a waiver, election, or acquiescence. No waiver hereunder shall be effective unless signed by Bank and then is only effective for the specific instance and purpose for which it was given.

9.7 Demand Waiver. Except as otherwise expressly set forth herein or as required by applicable law, Borrower waives demand, notice of default or dishonor, notice of payment and nonpayment, notice of any default, nonpayment at maturity, release, compromise, settlement, extension, or renewal of accounts, documents, instruments, chattel paper, and guarantees held by Bank on which Borrower is liable.

If to Borrower:   Bottomline Technologies, Inc.
                  155 Fleet Street
                  Portsmouth, New Hampshire 03801
                  Attn: Mr. Kevin Donovan
                  FAX: (603) 436-0300

with a copy to:   Hale and Dorr LLP
                  60 State Street
                  Boston, Massachusetts 02109
                  Attn: John Burgess, Esquire
                  FAX: (617) _______________

If to Bank:       Silicon Valley Bank
                  One Newton Executive Park, Suite 200
                  2221 Washington Street
                  Newton, Massachusetts 02462
                  Attn: Ms. Nancy Funkhouser
                  Fax: (617) 969-4395

with a copy to:   Riemer & Braunstein LLP
                  Three Center Plaza
                  Boston, Massachusetts 02108
                  Attn: David A. Ephraim, Esquire
                  FAX: (617) 880-3456

11 CHOICE OF LAW, VENUE AND JURY TRIAL WAIVER

Massachusetts law governs the Loan Documents without regard to principles of conflicts of law. Borrower and Bank each submit to the exclusive jurisdiction of the State and Federal courts in Massachusetts; provided,

however, that if for any reason Bank cannot avail itself of such courts in the Commonwealth of Massachusetts, Borrower accepts jurisdiction of the courts and venue in Santa Clara County, California. NOTWITHSTANDING THE FOREGOING, THE BANK
SHALL HAVE THE RIGHT TO BRING ANY ACTION OR PROCEEDING AGAINST THE BORROWER OR ITS PROPERTY IN THE COURTS OF ANY OTHER JURISDICTION WHICH THE BANK DEEMS NECESSARY OR APPROPRIATE IN ORDER TO REALIZE ON THE COLLATERAL OR TO OTHERWISE ENFORCE THE BANK'S RIGHTS AGAINST THE BORROWER OR ITS PROPERTY.

BORROWER AND BANK EACH WAIVE THEIR RIGHT TO A JURY TRIAL OF ANY CLAIM OR CAUSE OF ACTION ARISING OUT OF OR BASED UPON THIS AGREEMENT, THE LOAN DOCUMENTS OR ANY CONTEMPLATED TRANSACTION, INCLUDING CONTRACT, TORT, BREACH OF DUTY AND ALL OTHER CLAIMS. THIS WAIVER IS A MATERIAL INDUCEMENT FOR BOTH PARTIES TO ENTER INTO THIS AGREEMENT. EACH PARTY HAS REVIEWED THIS WAIVER WITH ITS COUNSEL.

12 GENERAL PROVISIONS

12.1 Successors and Assigns. This Agreement binds and is for the benefit of the successors and permitted assigns of each party. Borrower may not assign this Agreement or any rights or Obligations under it without Bank's prior written consent which may be granted or withheld in Bank's discretion. Bank has the right, without the consent of or prior notice to Borrower, to sell, transfer, negotiate, or grant participation in all or any part of, or any interest in, Bank's obligations, rights and benefits under this Agreement, the Loan Documents or any related agreement.

12.2 Indemnification. Borrower hereby indemnifies, defends and holds the Bank and its officers, employees and agents harmless against: (a) all obligations, demands, claims, and liabilities asserted by any other party in connection with the transactions contemplated by the Loan Documents; and (b) all losses or Bank Expenses incurred, or paid by Bank from, following, or consequential to transactions between Bank and Borrower under the Loan Documents (including reasonable attorneys' fees and expenses), except for losses caused by Bank's gross negligence or willful misconduct.

12.3 Right of Set-Off. Borrower and any guarantor hereby grant to Bank, a lien, security interest and right of setoff as security for all Obligations to Bank, whether now existing or hereafter arising upon and against all deposits, credits, collateral and property, now or hereafter in the possession, custody, safekeeping or control of Bank or any entity under the control of the Bank or in transit to any of them. At any time after the occurrence and during the continuance of an Event of Default, without demand or notice, Bank may set off the same or any part thereof and apply the same to any liability or obligation of Borrower and any guarantor even though unmatured and regardless of the adequacy of any other collateral securing the loan. ANY AND ALL RIGHTS TO REQUIRE BANK TO EXERCISE ITS RIGHTS OR REMEDIES WITH RESPECT TO ANY OTHER COLLATERAL WHICH SECURES THE LOAN, PRIOR TO EXERCISING ITS RIGHT OF SETOFF WITH RESPECT TO SUCH DEPOSITS, CREDITS OR OTHER PROPERTY OF THE BORROWER OR ANY GUARANTOR, ARE HEREBY KNOWINGLY, VOLUNTARILY AND IRREVOCABLY WAIVED.

12.4 Time of Essence. Time is of the essence for the performance of all Obligations in this Agreement.

12.5 Severability of Provision. Each provision of this Agreement is severable from every other provision in determining the enforceability of any provision.

12.6 Amendments in Writing; Integration. All amendments to this Agreement must be in writing signed by both Bank and Borrower. This Agreement and the Loan Documents represent the entire agreement about this subject matter, and supersede prior negotiations or agreements. All prior agreements, understandings,

representations, warranties, and negotiations between the parties about the subject matter of this Agreement and the Loan Documents merge into this Agreement and the Loan Documents.

12.7 Termination. Provided that all the Obligations then due have been repaid in full, this Agreement may be terminated by Borrower without premium or penalty.

12.8 Counterparts. This Agreement may be executed in any number of counterparts and by different parties on separate counterparts, each of which, when executed and delivered, are an original, and all taken together, constitute one Agreement.

12.9 Survival. All covenants, representations and warranties made in this Agreement continue in full force while any Obligations remain outstanding. The obligation of Borrower in Section 12.2 to indemnify Bank shall survive until the statute of limitations with respect to such claim or cause of action shall have run.

12.10 Confidentiality. In handling any confidential information, Bank shall exercise the same degree of care that it exercises for its own proprietary information, but disclosure of information may be made: (i) to Bank's subsidiaries or affiliates in connection with their business with Borrower; (ii) to prospective transferees or purchasers of any interest in the Credit Extensions (provided, however, Bank shall use commercially reasonable efforts in obtaining such prospective transferee's or purchaser's agreement to the terms of this provision); (iii) as required by law, regulation, subpoena, or other order,
(iv) as required in connection with Bank's examination or audit; and (v) as Bank considers reasonably necessary in exercising remedies under this Agreement. Confidential information does not include information that either: (a) is in the public domain or in Bank's possession when disclosed to Bank, or becomes part of the public domain after disclosure to Bank; or (b) is disclosed to Bank by a third party, if Bank does not know that the third party is prohibited from disclosing the information.

13 DEFINITIONS

13.1 Definitions.

"Accounts" are all existing and later arising accounts, contract rights, and other obligations owed Borrower in connection with its sale or lease of goods (including licensing software and other technology) or provision of services, all credit insurance, guaranties, other security and all merchandise returned or reclaimed by Borrower and Borrower's Books relating to any of the foregoing, as such definition may be amended from time to time according to the Code.

"Advance" or "Advances" is a loan advance (or advances) under the Committed Revolving Line.

"Affiliate" of a Person is a Person that owns or controls directly or indirectly the Person, any Person that controls or is controlled by or is under common control with the Person, and each of that Person's senior executive officers, directors, partners and, for any Person that is a limited liability company, that Person's managers and members.

"Bank Expenses" are all audit fees and expenses and reasonable costs or expenses (including reasonable attorneys' fees and expenses) for preparing, negotiating, administering, defending and enforcing the Loan Documents (including appeals or Insolvency Proceedings).

"Borrower's Books" are all Borrower's books and records including ledgers, records regarding Borrower's assets or liabilities, the Collateral, business operations or financial condition and all computer programs or discs or any equipment containing the information.

"Borrowing Base" is 80.0% of Eligible Accounts, as determined by Bank from Borrower's most recent Borrowing Base Certificate; provided, however, that Bank may adjust the percentage of the Borrowing Base after performing an audit of Borrower's Collateral.

"Business Day" is any day that is not a Saturday, Sunday or a day on which the Bank is closed.

"Closing Date" is the date of this Agreement.

"Code" is the Uniform Commercial Code as adopted in Massachusetts, as amended and as may be amended and in effect from time to time.

"Collateral" is any and all properties, rights and assets of the Borrower granted by the Borrower to Bank or arising under the Code, now, or in the future, in which the Borrower obtains an interest, or the power to transfer rights, including, without limitation, the property described on Exhibit A.

"Committed Revolving Line" is Five Million Dollars ($5,000,000.00).

"Contingent Obligation" is, for any Person, any direct or indirect liability, contingent or not, of that Person for (i) any indebtedness, lease, dividend, letter of credit or other obligation of another such as an obligation directly or indirectly guaranteed, endorsed, co-made, discounted or sold with recourse by that Person, or for which that Person is directly or indirectly liable; (ii) any obligations for undrawn letters of credit for the account of that Person; and (iii) all obligations from any interest rate, currency or commodity swap agreement, interest rate cap or collar agreement, or other agreement or arrangement designated to protect a Person against fluctuation in interest rates, currency exchange rates or commodity prices; but "Contingent Obligation" does not include endorsements in the ordinary course of business. The amount of a Contingent Obligation is the stated or determined amount of the primary obligation for which the Contingent Obligation is made or, if not determinable, the maximum reasonably anticipated liability for it determined by the Person in good faith; but the amount may not exceed the maximum of the obligations under the guarantee or other support arrangement.

"Credit Extension" is each Advance, Letter of Credit, or any other extension of credit by Bank for Borrower's benefit under this Agreement.

"Current Liabilities" are the aggregate amount of Borrower's Total Liabilities which mature within one (1) year, which shall include, without limitation, all obligations and liabilities of Borrower to Bank.

"Deferred Revenue" is as defined under GAAP.

"Eligible Accounts" are Accounts in the ordinary course of Borrower's business that meet all Borrower's representations and warranties in Section 5.2; but Bank may change eligibility standards by giving Borrower thirty (30) days prior written notice. Unless Bank agrees otherwise in writing, Eligible Accounts shall not include:

(a) Accounts that the account debtor has not paid within ninety (90) days of invoice date;

(b) Accounts for an account debtor, fifty percent (50%) or more of whose Accounts have not been paid within ninety (90) days of invoice date;

(c) Credit balances over ninety (90) days from invoice date;

(d) Accounts for an account debtor, including Affiliates, whose total obligations to Borrower exceed twenty-five (25%) of all Accounts, for the amounts that exceed that percentage, unless Bank approves in writing;

(e) Accounts for which the account debtor does not have its principal place of business in the United States;

(f) Accounts for which the account debtor is a federal, state or local government entity or any department, agency, or instrumentality thereof;

(g) Accounts for which Borrower owes the account debtor, but only up to the amount owed (sometimes called "contra" accounts, accounts payable, customer deposits or credit accounts);

(h) Accounts for demonstration or promotional equipment, or in which goods are consigned, sales guaranteed, sale or return, sale on approval, or other terms if account debtor's payment may be conditional;

(i) Accounts for which the account debtor is Borrower's Affiliate, officer, employee, or agent;

(j) Accounts in which the account debtor disputes liability or makes any claim and Bank believes there may be a basis for dispute (but only up to the disputed or claimed amount), or if the Account Debtor is subject to an Insolvency Proceeding, or becomes insolvent, or goes out of business;

(k) Accounts for which Bank reasonably determines after inquiry and consultation with Borrower collection to be doubtful.

"Equipment" is all present and future machinery, equipment, tenant improvements, furniture, fixtures, vehicles, tools, parts and attachments in which Borrower has any interest.

      "ERISA" is the Employment Retirement Income Security Act of 1974, and its
regulations.

      "GAAP" is generally accepted accounting principles.

"Indebtedness" is (a) indebtedness for borrowed money or the deferred price of property or services, such as reimbursement and other obligations for surety bonds and letters of credit, (b) obligations evidenced by notes, bonds, debentures or similar instruments, (c) capital lease obligations and (d) Contingent Obligations.

"Insolvency Proceeding" is any proceeding by or against any Person under the United States Bankruptcy Code, or any other bankruptcy or insolvency law, including assignments for the benefit of creditors, compositions, extensions generally with its creditors, or proceedings seeking reorganization, arrangement, or other relief.

"Intellectual Property" is any and all copyright rights, copyright applications, copyright registrations and like protections in each work of authorship and derivative work thereof, whether published or unpublished; any and all trade secrets, and any and all intellectual property rights in computer software and computer software products; any and all design rights which may be available to Borrower; all mask work or similar rights available for the protection of semiconductor chips; all patents, patent applications and like protections; any trademark and servicemark rights, whether registered or not, applications to register and registrations of the same and like protections; all licenses or other rights to use any of the foregoing; or any claims for damages by way of any past, present and future infringement of any of the foregoing.

"Inventory" is present and future inventory in which Borrower has any interest, including merchandise, raw materials, parts, supplies, packing and shipping materials, work in process and finished products intended for sale or lease or to be furnished under a contract of service, of every kind and description now or later owned by or in the custody or possession, actual or constructive, of Borrower, including inventory temporarily out of its custody or possession or in transit and including returns on any accounts or other proceeds (including insurance proceeds) from the sale or disposition of any of the foregoing and any documents of title.

"Investment" is any beneficial ownership of (including stock, partnership interest or other securities) any Person, or any loan, advance or capital contribution to any Person.

"Letter of Credit" means a letter of credit or similar undertaking issued by Bank pursuant to Section 2.1.2.

"Letter of Credit Reserve" has the meaning set forth in Section 2.1.2.

"Lien" is a mortgage, lien, deed of trust, charge, pledge, security interest or other encumbrance.

"Loan Documents" are, collectively, this Agreement, any note, or notes or guaranties executed by Borrower or Guarantor, and any other present or future agreement between Borrower and/or for the benefit of Bank in connection with this Agreement, all as amended, extended or restated.

"Material Adverse Change " is: (i) A material impairment in the perfection or priority of Bank's security interest in the Collateral or in the value of such Collateral; (ii) a material adverse change in the business, operations, or condition (financial or otherwise) of the Borrower; or (iii) a material impairment of the prospect of repayment of any portion of the Obligations ;or
(iv) Bank determines, based upon information available to it and in its reasonable judgment, that there is a reasonable likelihood that Borrower shall fail to comply with one or more of the financial covenants in Section 6 during the next succeeding financial reporting period.

"Net Loss" is a reconciled amount that is calculated as the net loss of the Borrower (on a consolidated basis) as determined by GAAP, and adjusted by adding back, without duplication (i) amortization of acquisition intangibles,
(ii) acquisition stock compensation expense and (iii) non-cash charges related to the issuance of warrants.

"Obligations" are debts, principal, interest, Bank Expenses and other amounts Borrower owes Bank now or later under this Agreement, including letters of credit, cash management services, and foreign exchange contracts, if any, and including interest accruing after Insolvency Proceedings begin.

"Permitted Indebtedness" is:

(a) Borrower's indebtedness to Bank under this Agreement or the Loan Documents;

(b) Indebtedness existing on the Closing Date and shown on the Schedule;

(c) Subordinated Debt;

(d) Indebtedness to trade creditors incurred in the ordinary course of business;

(e) Indebtedness incurred for the purchase or lease of Equipment not to exceed $1,000,000.00 in the aggregate during the term hereof, which Indebtedness may be secured in accordance with subsection (c) of the definition of Permitted Liens;

(f) Indebtedness secured by Permitted Liens other than subsection
(c) thereof;

(g) Extensions, refinancings, modifications, amendments and restatements of any items of Permitted Indebtedness (a) through (f) above, provided that the principal amount thereof is not increased or the terms thereof are not modified to impose more burdensome terms upon Borrower.

"Permitted Investments" are:

(a) Investments shown on the Investments Schedule and existing on the Closing Date;

(b) Equity Investments of a strategic nature in an aggregate outstanding amount not to exceed $1,000,000.00;

(c) Loans or advances to Borrower's employees as determined by Borrower's management up to an aggregate outstanding amount of $100,000 at any time; and

(d) (i) marketable direct obligations issued or unconditionally guaranteed by the United States or its agency or any state maturing within 1 year from its acquisition, (ii) commercial paper maturing no more than 1 year after its creation and having the highest rating from either Standard & Poor's Corporation or Moody's Investors Service, Inc., (iii) Bank's certificates of deposit issued maturing no more than 1 year after issue,
(iv) any other investments administered through the Bank, and (v) equity investments of a strategic nature consistent with Borrower's investment policy previously delivered to Bank.

"Permitted Liens" are:

(a) Liens existing on the Closing Date and shown on the Schedule or arising under this Agreement or other Loan Documents;

(b) Liens for taxes, fees, assessments or other government charges or levies, either not delinquent or being contested in good faith and for which Borrower maintains adequate reserves on its Books, if they have no priority over any of Bank's security interests;

(c) Purchase money Liens (i) on Equipment acquired or held by Borrower incurred for financing the acquisition of the Equipment, or (ii) existing on equipment when acquired, if the Lien is confined to the property and improvements and the proceeds of the equipment;

(d) Carriers', warehousemen's, mechanics', materialmen's repairmen's or other like liens arising in the ordinary course of business which are not overdue for a period of more than ninety (90) days or which are being contested in good faith by appropriate proceedings;

(e) Leases or subleases and non-exclusive licenses or sublicenses granted in the ordinary course of Borrower's business, if the leases, subleases, licenses and sublicenses permit granting Bank a security interest; and

(f) Liens incurred in the extension, renewal or refinancing of the indebtedness secured by Liens described in (a) through (e), but any extension, renewal or replacement Lien must be limited to the property encumbered by the existing Lien and the principal amount of the indebtedness may not increase.

"Person" is any individual, sole proprietorship, partnership, limited liability company, joint venture, company, trust, unincorporated organization, association, corporation, institution, public benefit corporation, firm, joint stock company, estate, entity or government agency.

"Prime Rate" is Bank's most recently announced "prime rate," even if it is not Bank's lowest rate.

"Quick Assets" is, on any date, the Borrower's consolidated, unrestricted cash held by Bank, cash equivalents held by Bank, net billed accounts receivable and investments with maturities of fewer than 12 months held by Bank, determined according to GAAP; provided that until March 1, 2002, unrestricted cash or cash equivalents on deposit by Borrower with Fleet National Bank shall be included as Quick Assets herein.

"Responsible Officer" is each of the Chief Executive Officer, President, Chief Financial Officer and Treasurer of Borrower.

"Revolving Maturity Date" is the date which is twelve months from the Closing Date.

"Schedule" is any attached schedule of exceptions.

"Subordinated Debt" is debt incurred by Borrower subordinated to Borrower's debt to Bank (pursuant to a subordination agreement entered into between the Bank, the Borrower and the subordinated creditor), on terms acceptable to Bank.

IN WITNESS WHEREOF, the parties hereto have caused this Agreement to be executed as a sealed instrument under the laws of the Commonwealth of Massachusetts as of the date first above written.

BORROWER:

BOTTOMLINE TECHNOLOGIES (de), INC.

By: /s/ Robert Eberle

------------------------------------------

Name: Robert Eberle

Title: Exec VP, COO & CFO

BANK:

SILICON VALLEY BANK, d/b/a
SILICON VALLEY EAST

By: /s/ Nancy Funkhouser

------------------------------------------

Name: Nancy Funkhouser

Title: Vice President

SILICON VALLEY BANK

By: /s/ Maggie Garcia

------------------------------------------

Name: Maggie Garcia

EXHIBIT A

The Collateral consists of all right, title and interest of Borrower in and to the following:

All goods, equipment, inventory, contract rights or rights to payment of money, license agreements, franchise agreements, general intangibles (including payment intangibles), accounts (including health-care receivables), documents, instruments (including any promissory notes), chattel paper (whether tangible or electronic), cash, deposit accounts, fixtures, letters of credit rights (whether or not the letter of credit is evidenced by a writing), commercial tort claims, securities, and all other investment property supporting obligations, and financial assets, whether now owned or hereafter acquired, wherever located; and

All Borrower's Books relating to the foregoing and any and all claims, rights and interests in any of the above and all substitutions for, additions, attachments, accessories, accessions and improvements to and replacements, products, proceeds and insurance proceeds of any or all of the foregoing.

Notwithstanding the foregoing, the Collateral does not include, in any event:

Any and all copyright rights, copyright applications, copyright registrations and like protections in each work of authorship and derivative work thereof, whether published or unpublished; any and all trade secrets, and any and all intellectual property rights in computer software and computer software products; any and all design rights which may be available to Borrower; all mask work or similar rights available for the protection of semiconductor chips; all patents, patent applications and like protections; any trademark and servicemark rights, whether registered or not, applications to register and registrations of the same and like protections; all licenses or other rights to use any of the foregoing; or any claims for damages by way of any past, present and future infringement of any of the foregoing. Notwithstanding the foregoing, the Collateral shall include all accounts, license and royalty fees and other revenues, proceeds, or income arising out of or relating to any of the foregoing intellectual property. To the extent a court of competent jurisdiction holds that a security interest in any Intellectual Property is necessary to have a security interest in any accounts, license and royalty fees and other revenues, proceeds, or income arising out of or relating to any of the foregoing Intellectual Property, then the Collateral shall, effective as of the Closing Date, include the Intellectual Property, to the extent necessary to permit perfection of the Bank's security interest in such accounts, license and royalty fees and other revenues, proceeds, or income arising out of or relating to any of the Intellectual Property and to the extent such inclusion is not violative of, prohibited by or would trigger an adverse consequence under any material agreement relating to such Intellectual Property or applicable law.

Fax To: (617) 969-5965                                Date: ____________________

--------------------------------------------------------------------------------
LOAN PAYMENT:

                     Sample documents Client Name (Borrower)

From Account #_______________________            To Account #___________________
                  (Deposit Account #)                           (Loan Account #)

Principal $_____________________ and/or Interest $______________________________

All Borrower's representation and warranties in the Loan and Security Agreement are true, correct and complete in all material respects to on the date of the telephone transfer request for and advance, but those representations and warranties expressly referring to another date shall be true, correct and complete in all material respects as of the date:

Authorized Signature: _________________________ Phone Number: __________________

LOAN ADVANCE:

Complete Outgoing Wire Request section below if all or a portion of the funds from this loan advance are for an outgoing wire.

From Account #______________________ To Account #______________________

(Loan Account #) (Deposit Account #)

Amount of Advance $______________________

All Borrower's representation and warranties in the Loan and Security Agreement are true, correct and complete in all material respects to on the date of the telephone transfer request for and advance, but those representations and warranties expressly referring to another date shall be true, correct and complete in all material respects as of the date:

Authorized Signature: _________________________ Phone Number: __________________

Beneficiary Name: ____________________________    Amount of Wire: $_____________

Beneficiary Bank: ____________________________    Account Number: ______________

City and Sate: _______________________________

Beneficiary Bank Transit (ABA) #: ____________    Beneficiary Bank Code
                                                   (Swift, Sort, Chip, etc.):
                                                   (For International Wire Only)

Intermediary Bank: ___________________________    Transit (ABA) #: _____________

For Further Credit to: _________________________________________________________

Special Instruction: ___________________________________________________________

By signing below, I (we) acknowledge and agree that my (our) funds transfer request shall be processed in accordance with and subject to the terms and conditions set forth in the agreements(s) covering funds transfer service(s), which agreements(s) were previously received and executed by me (us).

Authorized Signature: ___________________

Print Name/Title: _______________________

Telephone # _____________________________

2nd Signature (If Required): ____________

Print Name/Title: _______________________

Telephone # _____________________________

EXHIBIT C

BORROWING BASE CERTIFICATE

Borrower: Bottomline Technologies (de), Inc. Lender: Silicon Valley Bank

Commitment Amount: $5,00,000.00

ACCOUNTS RECEIVABLE
1. Accounts Receivable Book Value as of ___________ $_______________
2. Additions (please explain on reverse) $_______________
3. TOTAL ACCOUNTS RECEIVABLE $_______________

ACCOUNTS RECEIVABLE DEDUCTIONS (without duplication)

4. Amounts over 90 days due $_______________
5. Balance of 50% over 90 day accounts $_______________
6. Credit balances over 90 days $_______________
7. Concentration Limits $_______________
8. Foreign Accounts $_______________
9. Governmental Accounts $_______________
10. Contra Accounts $_______________
11. Promotion or Demo Accounts $_______________
12. Intercompany/Employee Accounts $_______________
13. Other (please explain on reverse) $_______________
14. TOTAL ACCOUNTS RECEIVABLE DEDUCTIONS $_______________
15. Eligible Accounts (#3 minus #14) $_______________
16. LOAN VALUE OF ACCOUNTS ( 80% of #15) $_______________

BALANCES

17. Maximum Loan Amount $_______________
18. Total Funds Available (Lesser of #17 or #16) $_______________
19. Present balance owing on Line of Credit $_______________
20. Outstanding under Sublimits (letters of credit ) $_______________
21. RESERVE POSITION (#18 minus #19 and #20) $_______________

The undersigned represents and warrants that this is true, complete and correct, and that the information in this Borrowing Base Certificate complies with the representations and warranties in the Loan and Security Agreement between the undersigned and Silicon Valley Bank.

                                              ----------------------------------
COMMENTS:                                               BANK USE ONLY

                                              Received by: _____________________
By: ___________________________                              AUTHORIZED SIGNER
           Authorized Signer
                                              Date: ____________________________

                                              Verified: ________________________
                                                             AUTHORIZED SIGNER

                                              Date: ____________________________

                                              ----------------------------------

EXHIBIT D

COMPLIANCE CERTIFICATE

TO: SILICON VALLEY BANK

FROM: BOTTOMLINE TECHNOLOGIES (de), INC.

The undersigned authorized officer of BOTTOMLINE TECHNOLOGIES (de), INC. certifies that under the terms and conditions of the Loan and Security Agreement between Borrower and Bank (the "Agreement"), (i) Borrower is in complete compliance for the period ending _______________ with all required covenants except as noted below and (ii) all representations and warranties in the Agreement are true and correct in all material respects on this date. Attached are the required documents supporting the certification. The Officer certifies that these are prepared in accordance with Generally Accepted Accounting Principles (GAAP) consistently applied from one period to the next except as explained in an accompanying letter or footnotes. The Officer acknowledges that no borrowings may be requested at any time or date of determination that Borrower is not in compliance with any of the terms of the Agreement, and that compliance is determined not just at the date this certificate is delivered.

Please indicate compliance status by circling Yes/No under "Complies" column.

Reporting Covenant                      Required                  Complies
------------------                      --------                  --------

Monthly financial statements            Monthly within 30 days    Yes   No
  with CC
Annual(CPA Audited)                     FYE within 90 days        Yes   No
10-Q, 10-K and 8-K                      Within 10 days after      Yes   No
                                          filing with SEC
BBC A/R Agings                          Monthly within 30 days    Yes   No

Financial Covenant                      Required       Actual     Complies
------------------                      --------       ------     --------

Maintain on a Monthly  Basis:
Minimum Adjusted Quick Ratio            2.0:1.0        _____:1.0  Yes   No

Profitability(net loss/min profit)      $_*_______     $________  Yes   No

Sincerely,
                                              Received by: _____________________
_____________________________                                  AUTHORIZED SIGNER
SIGNATURE                                     Date: ____________________________

_____________________________                 Verified: ________________________
TITLE                                                        AUTHORIZED SIGNER

_____________________________                 Date: ____________________________

DATE

Exhibit 10.2

NEGATIVE PLEDGE AGREEMENT

This Negative Pledge Agreement is made as of December 28, 2001, by and between BOTTOMLINE TECHNOLOGIES (de), INC. ("Borrower") and SILICON VALLEY BANK, a California-chartered bank, with its principal place of business at 3003 Tasman Drive, Santa Clara, California 95054 and with a loan production office located at One Newton Executive Park, Suite 200, 2221 Washington Street, Newton, Massachusetts 02462, doing business under the name "Silicon Valley East" ("Bank").

In connection with, among other documents, the Loan and Security Agreement (the "Loan Documents") being concurrently executed herewith between Borrower and Bank, Borrower agrees as follows:

1. Except for the granting of non-exclusive licenses or sublicenses by Borrower in the ordinary course of business, Borrower has not, and shall not, sell, transfer, assign, mortgage, pledge, lease, grant a security interest in, or encumber any of Borrower's Intellectual Property (as defined below).

2. Borrower has not, and shall not, enter into a negative pledge agreement, or similar agreement, affecting the rights of the Intellectual Property with any other party.

3. It shall be an event of default under the Loan Documents between Borrower and Bank if there is a breach of any term of this Negative Pledge Agreement.

4. As used herein,

a. "Intellectual Property" means:

(i) Any and all Copyrights;

(ii) Any and all trade secrets, and any and all intellectual property rights in computer software and computer software products now or hereafter existing, created, acquired or held;

(iii) Any and all design rights which may be available to Borrower now or hereafter existing, created, acquired or held;

(iv) All Mask Works or similar rights available for the protection of semiconductor chips;

(v) All Patents;

(vi) Any Trademarks;

(vii) Any and all claims for damages by way of past, present and future infringements of any of the rights included above, with the right, but not the obligation, to sue for and collect such damages for said use or infringement of the intellectual property rights identified above;

(viii) All licenses or other rights to use any of the Copyrights, Patents, Trademarks, or Mask Works and all license fees and royalties arising from such use to the extent permitted by such license or rights; and

(ix) All amendments, extensions, renewals and extensions of any of the Copyrights, Trademarks, Patents, or Mask Works; and

(x) All proceeds and products of the foregoing, including without limitation all payments under insurance or any indemnity or warranty payable in respect of any of the foregoing.

b. "Copyrights" means any and all copyright rights, copyright applications, copyright registrations and like protections in each work of authorship and derivative work thereof, whether published or unpublished and whether or not the same also constitutes a trade secret, now or hereafter existing, created, acquired or held.

c. "Mask Works" means all mask work or similar rights available for the protection of semiconductor chips, now owned or hereafter acquired;

d. "Patents" means all patents, patent applications and like protections including without limitation improvements, divisions, continuations, renewals, reissues, extensions and continuations-in-part of the same.

e. "Trademarks" means any trademark and servicemark rights, whether registered or not, applications to register and registrations of the same and like protections, and the entire goodwill of the business of Borrower connected with and symbolized by such trademarks.

5. Capitalized terms used but not otherwise defined herein shall have the same meaning as in the Loan Documents.

6. The laws of the Commonwealth of Massachusetts shall apply to this Agreement. BORROWER ACCEPTS FOR ITSELF AND IN CONNECTION WITH ITS PROPERTIES, UNCONDITIONALLY, THE NON-EXCLUSIVE JURISDICTION OF ANY STATE OR FEDERAL COURT OF COMPETENT JURISDICTION IN THE COMMONWEALTH OF MASSACHUSETTS IN ANY ACTION, SUIT, OR PROCEEDING OF ANY KIND, AGAINST IT WHICH ARISES OUT OF OR BY REASON OF THIS AGREEMENT; PROVIDED, HOWEVER, THAT IF FOR ANY REASON BANK CANNOT AVAIL ITSELF OF THE COURTS OF THE COMMONWEALTH OF MASSACHUSETTS, BORROWER ACCEPTS JURISDICTION OF THE COURTS AND VENUE IN SANTA CLARA COUNTY, CALIFORNIA.

7. This Agreement shall terminated upon repayment in full of all Obligations (as defined in the Loan and Security Agreement) and the termination of Bank's commitment to lend under any Loan Documents.

8. This Agreement shall become effective only when it shall have been executed by Borrower and Bank (provided, however, in no event shall this Agreement become effective until signed by an officer of Bank in California).

EXECUTED as a sealed instrument under the laws of the Commonwealth of Massachusetts as of the date first written above.

BORROWER:

BOTTOMLINE TECHNOLOGIES (de), INC.

By:     /s/  Robert Eberle
    ------------------------------
Name: Robert A. Eberle
      ----------------------------
Title:  Exec. VP, COO & CFO
      ----------------------------

BANK:

SILICON VALLEY BANK d/b/a SILICON
VALLEY EAST

By:  /s/  Nancy E. Funkhouser
    ------------------------------
Name: Nancy E. Funkhouser
      ----------------------------
Title:  Vice President
       ---------------------------

SILICON VALLEY BANK

By:  /s/ Maggie Garcia
    ------------------------------
Name:  Maggie Garcia
      ----------------------------
Title: Loan Admin. Team Leader
      ----------------------------
(Signed in Santa Clara, California)

Confirmation of Committed Business Overdraft                      [LOGO] NatWest
Facility

Private and Confidential                                Branch Address:
S Cutler Esq                                            13 Market Place
Bottomline Technologies Europe Ltd                      READING
Chatham Street                                          Berkshire
READING                                                 RG1 2EP
Berkshire
RG1 7JX

Facility Account:                   67486932 (60-17-21)
Overdraft Limit:                    (pound)2,000,000 (two million pounds)
Agreed Interest Rate:               2% per annum over the Bank's Base Rate
Bank's Base Rate:                   currently 4% per annum (but may vary from
                                    time to time)
Interest Frequency:                 quarterly

Unarranged Borrowing Rate:          4% per annum over the Bank's Base Rate (but
                                    may vary from time to time subject to one
                                    month's notice)
Arrangement & Commitment Fee:       (pound)8125
Expiry Date:                        31 December 2002

Principal Terms

1. We offer you a committed overdraft facility (the Facility) subject to the terms of this Confirmation and the Committed Overdraft General Terms (COGT) attached.

2. Provided that none of the Events of Default detailed in Clause 3 occur, the Facility will be available until the Expiry Date.

3. If any of the following events (Events of Default) occurs, we may, by giving written notice, demand immediate repayment of the outstanding borrowing in the Facility account, require that the amounts from time to time owing under the Facility become repayable on demand or cancel the Facility and exercise our rights under any security:-

(a) the Overdraft Limit is exceeded;
(b) the commencement of any winding-up, bankruptcy of administration proceeding against you or the appointment of a receiver or administrative receiver in respect of any of your property or you make arrangements with creditors;

(c) if you are a sole trader, you die;
(d) your business ceases to trade or, if you are a partnership, the partnership is dissolved;
(e) any procedure is used against you to attach or take possession of any property for payment of a debt;
(f) you are in breach of any financial obligation to us or any other creditor;
(g) you fail to provide any information regarding your financial condition or business operations detailed in Clause 5; or
(h) any information given to us is inaccurate or there is a material non-disclosure by you to us.

4. Interest will be charged:-

(a) up to the Overdraft Limit, at the Agreed Interest Rate; and
(b) in excess of the Overdraft Limit (or borrowing outstanding after the Expiry Date or after we have demanded immediate repayment if the outstanding borrowing on the Facility Account in terms of Clause 3 of this Confirmation or Clause C of the COGT), at the Unarranged Borrowing Rate.

5. To enable us to monitor the Facility you will provide:-

(a) as soon as they become available but in any event within 180 days after the end of your financial year and in a format acceptable to us, copies of your business accounts for that year;

(b) as soon they become available but in any event no later than 30 days after the end of the accounting period to which they relate and in a format acceptable to us, monthly management accounts incorporating balance sheet, profit and loss account, and aged list of debtors and creditors; and

(c) promptly, such further information regarding your financial condition and business operations as we may reasonably request (including audited business/management accounts where not already supplied).

6. The Arrangement Fee will be debited by us to the Facility Account on the date of this Confirmation or shortly thereafter.

7. The Facility will be secured as set out in an attached Schedule. We shall not be obliged to provide the Facility until any such security is completed to our satisfaction. All security will require to be granted in our standard form.

8. We are not obliged to provide the Facility until you have accepted the Facility on the terms set out in this Confirmation and COGT by returning the duplicate of this Confirmation to us duly signed.

For National Westminster Bank Plc

/s/ Paul Marston

PAUL MARSTON ACIB AMCT
Corporate Manager

18 December 2001

Having decided that the Facility is appropriate and in our interests, it is hereby accepted on the terms set out in this Confirmation and the COGT attached.

Signature /s/ P. Fortune                    Date 21/12/01
          --------------------------------       -----------------

Signature /s/ S.J. Cutler                   Date 21/12/01
          --------------------------------       -----------------

Committed Overdraft General Terms (COGT)

These COGT explain your and our rights and responsibilities in respect of the Facility and should be read in conjunction with the Confirmation attached specified to the Facility. Definitions and meanings used in the Confirmation attached also apply in these COGT (and vice versa) unless the context require otherwise. Our "Code of practice for business banking" and "Services and charges for business customers" booklets are available on request.

A. Overdraft Limit

The Facility enables you to overdraw the Facility Account up to the Overdraft Limit. The Overdraft Limit should not be exceeded without our prior consent and we may refuse to allow any payment or withdrawal which could have that effect. If we allow a payment or withdrawal or a series of payments or withdrawals which results in the Overdraft Limit being exceeded, it will not mean that the Overdraft Limit has changed or that we are bound to allow any other payment or withdrawal which could result in the Overdraft Limit being exceeded at other times.

We may debit the Facility Account under Clause D and E of these COGT even if it results in the Overdraft Limit being exceeded.

B. Uncleared credits

We may disregard any uncleared credits when calculating the amount outstanding under the Facility (and any interest payable). If however we pay a cheque or cheques (or allow any other payment or withdrawal or a series of payments or withdrawals) against uncleared credits at any time we are not bound to do so at other times.

C. Renewal of Facility

At any time during the 30 days prior the Expiry Date you may request (or we may offer) to renew the Facility for a further period of up to 365 days, subject to us undertaking a full credit assessment and further documentation. If the Facility is not renewed before the Expiry Date any borrowing outstanding under the Facility will become repayable on demand and the Facility may be unconditionally cancelled by us at any time.

D. Interest

Interest will be calculated both before and after demand, decree or judgment on a daily basis on the cleared debit balance and will be debited by us to the Facility Account at the Interest Frequency on our usual charging days.

E. Costs/Charges

If the Overdraft Limit is exceeded (or if any borrowing is outstanding after the Expiry Date or after the date on which we demand immediate repayment of the Facility) our published charges for unarranged borrowing will apply. You will be given at least one month's notice of any changes to our published charges. You must pay any costs incurred by us in connection with the Facility whether as a result of you breaking the terms of the Facility or not. These costs will include (but not be limited to) costs of taking and discharging any security; taking steps, including court action, to obtain payment; enforcing and/or preserving the Bank's rights under any security held for the Facility; tracing you if you change address without notice and communicating with you of you break the terms of the Facility or an Event of Default occurs. We may debit such costs to the Facility Account.

F. Change in law, regulations or directive

If as a result of a change of any applicable law, regulation or directive, the cost to us of providing the Facility (including the cost of any undrawn portion of the Facility) increases we may, upon one month's written notice, convert the Facility into an overdraft repayable on demand and/or otherwise vary the terms and conditions of the Facility, including effecting an increase in the interest charged to reflect the increased cost of providing the Facility.

G. Set off

We shall be entitled to set-off against any of your liabilities under this agreement (whether present, future, actual or contingent) any of your credit balances (whether subject to notice or not) on any of your accounts with us in your name. We do not have to give you any prior notice to do this.

H. Joint and several liability

If you are more than one person then the word "you" shall refer to such persons both together and separately and the obligations of those persons under the Facility shall be joint and several, that is to say, each of you can be held liable both jointly and individually for all of the obligations under the Facility.

I. Miscellaneous

(a) These terms will not be affected by the Facility Account being allocated another account number by us or being transferred to another of our branches, offices or departments. In the event of a conflict between (i) the terms of the Confirmation attached and these COGT and (ii) any other terms which apply to the Facility Account then the terms of the Confirmation attached and these COGT will prevail.

(b) Without any obligation upon us to do so, we shall be entitled to allow you extended time to pay or grant you any other concession without affecting any of our rights in whole or in part.

[LOGO] NatWest

This is the Schedule referred to in the Bank's Confirmation of Committed Business Overdraft Facility to the Customer dated: 18 December 2001

Customer: Bottomline Technologies Europe Ltd

The overdraft facility made by the Bank to the Customer in terms of the Confirmation of Committed Business Overdraft Facility shall be secured by the following:-

(a) Motgage Debenture

(b) 1st Legal Mortgage over the freehold property known as 115 Chatham Street, Reading

Definitions

Mortgagor:               Bottomline Technologies Europe Limited
                                                        Company Number: 01911956

Bank:                    National Westminster Bank Plc

Interest:                Interest at the rate(s) charged to the Mortgagor by the
                         Bank for time to time

Property:                Administrative Area :      Reading

                         Description         :      115 Chatham Street

                         Tenure              :      Freehold

                         Title Number        :      BK110384

Charged Assets:          The assets charged by Clause 1.2

Goodwill:                The present and future goodwill of any business carried
                         on at the Property by or on behalf of the Mortgagor

Mortgagor's              Obligations: All the Mortgagor's liabilities to the
                         Bank of any kind and in any currency (whether present
                         or future actual or contingent and whether incurred
                         alone or jointly with another) together with the Bank's
                         charges and commission Interest and Expenses

Expenses:                All expenses (on a full indemnity basis) incurred by
                         the Bank or any Receiver at any time in connection with
                         the Property the Charged Assets the Goodwill or the
                         Mortgagor's Obligations or in taking or perfecting this
                         deed or in preserving defending or enforcing the
                         security created by this deed or in exercising any
                         power under this deed or otherwise with Interest from
                         the date they are incurred.

Required Currency:       The currency or currencies in which the Mortgagor's
                         Obligations are expressed from time to time

Charge

1       The Mortgagor covenants to discharge on demand the Mortgagor's
        Obligations and as a continuing security for such discharge and with
        full title guarantee charges to the Bank:-

1.1     By way of legal mortgage of all legal interests and otherwise by way of
        fixed charge the Property (to the full extent of the Mortgagor's
        interest in the Property or its proceeds of sale)

1.2     By way of fixed charge if the Mortgagor is a company:-

1.2.1   All the plant machinery and fixtures and fittings of the Mortgagor now
        and in the future at the Property

1.2.2   All furniture furnishings equipment tools and other chattels of the
        Mortgagor now and in the future at the Property and not regularly
        disposed of in the ordinary course of business

1.3     By way of fixed charge the Goodwill and the proceeds of any insurance
        from time to time affecting the Property or the Charged Asset

Repair Alteration and Insurance

2.1 The Mortgagor will keep the Property and the Charged Assets in good condition and comprehensively insured to the Bank's reasonable satisfaction for their full reinstatement cost and in default the Bank (without becoming liable to account as mortgagee in possession) may enter and repair or insure the Property and the Charged Assets. The Mortgagor will deposit with the Bank the insurance policy or where the Bank agrees a copy of it

2.2 The Mortgagor will not without the prior written consent of the Bank make any alteration to the Property which would require Planning Permission or approval under any Building Regulations

2.3 The Mortgagor will hold in trust for the Bank all money received under any insurance of the Property or the Charged Assets and at the Bank's option will apply the same in making good the relevant loss or damage or in or towards discharge of the Mortgagor's Obligations

Restrictions on Charging Leasing Disposing and Parting with possession

3.1     The mortgagor will not without the Bank's prior written consent:-

3.1.1   Create or permit to arise any mortgage charge or lien on the Property
        the Charged Assets or the Goodwill

3.1.2   Grant or accept a surrender of any lease or licence of the Property the
        Charged Assets or the Goodwill

3.1.3   Dispose of or part with or share possession or occupation of the
        Property the Charged Assets or the Goodwill

3.2     The Mortgagor requests the Chief Land Registrar to enter a restriction
        on the Register of any Registered Land that except under an order of the
        Registrar no disposition by the proprietor(s) of the land is to be
        registered without the consent of the registered proprietor of this deed

Powers of the Bank

4.1 The Bank may without restriction grant or accept surrenders of leases of the Property and the Charged Assets

4.2 Section 103 of the Law of Property Act 1925 shall not apply and the Bank may exercise its power of sale and other powers under that or any other Act or this deed at any time after the date of this deed

4.3 The Bank may under the hand of any official or manager or by deed appoint or remove a Receiver or Receivers of the Property the Charged Assets and the Goodwill and may fix and pay the fees of a Receiver but any Receiver shall be deemed to be the agent of the Mortgagor and the Mortgagor shall be solely responsible for the Receiver's acts defaults and remuneration

4.4 All or any of the powers conferred on a Receiver by Clause 5 may be exercised by the Bank without first appointing a Receiver or notwithstanding any appointment

4.5 The Bank will not be liable to account to the Mortgagor as mortgagee in possession for any money not actually received by the Bank

4.6 Section 93(1) of the Law of Property Act 1925 shall not apply to this deed

4.7 In addition to any lien or right to which the Bank may be entitled by law the Bank may from time to time without notice and both before and after demand set off the whole or any part of the Mortgagor's Obligations against any deposit or credit balance on any account of the Mortgagor with the Bank (whether or not that deposit or balance is due to the Mortgagor)

4.8 Despite any term to the contrary in relation to any deposit or credit balance on any account of the Mortgagor with the Bank that deposit or balance will not be capable of being assigned dealt with mortgaged or charged and will not be repayable to the Mortgagor before all the Mortgagor's Obligations have been discharged but the Bank may without prejudice to this deed permit the Mortgagor to make withdrawals from time to time

4.9 The Bank may exchange or convert to the Required Currency any currency held or received

5.1.1   To take possession of and generally manage the Property and the Charged
        Assets and any business carried on at the Property

5.1.2   To carry out on the Property any new works or complete any unfinished
        works of building reconstruction maintenance furnishing or equipment

5.1.3   To purchase or acquire any land or other property and purchase acquire
        grant or release any interest in or right over land or the benefit of
        any covenants (positive or restrictive) affecting land

5.1.4   To sell lease surrender or accept surrenders of leases charge or
        otherwise deal with and dispose of the Property the Charged Assets and
        the Goodwill without restriction including (without limitation) power to
        dispose of any fixtures separately from the Property

5.1.5   To carry into effect and complete any transaction by executing deeds or
        documents in the name of or on behalf of the Mortgagor

5.1.6   To take continue or defend any proceedings and enter into any
        arrangement or compromise

5.1.7   To insure the Property and the Charged Assets and any works and effect
        indemnity insurance or other similar insurance and obtain bonds and give
        indemnities and security to any bondsmen

5.1.8   To employ advisers consultants managers agents workmen and others and
        purchase or acquire materials tools equipment goods or supplies

5.1.9   To borrow any money and secure the payment of any money in priority to
        the Mortgagor's Obligations for the purpose of the exercise of any of
        his powers

5.1.10  To do any other acts which the Receiver may consider to be incidental or
        conductive to any of his powers or to the realization of the Property
        the Charge Assets and the Goodwill

5.2     If the Mortgagor is not a company the Mortgagor grants to such Receiver
        an irrevocable licence and power to use in connection with any business
        carried on at the Property all property of the Mortgagor at the Property
        when the Receiver is appointed and to remove store sell and/or dispose
        of any such property. The Receiver will account to the Bank for the
        proceeds of any sale of such property after deducting all costs and
        expenses incurred in the sale and that amount shall be a debt due from
        the Bank to the Mortgagor

5.3     A Receiver shall apply all money he receives first in repayment of all
        money borrowed by him and his expenses and liabilities and in payment of
        his fees and secondly towards the remaining matters specified in Section
        109(8) of the Law of Property Act 1925

Power of Attorney

6 The Mortgagor irrevocably appoints the Bank and any Receiver severally to be the Attorney of the Mortgagor (with full power of substitution and delegation) in the Mortgagor's name and on the Mortgagor's behalf and as the Mortgagor's act and deed to sign or execute all deeds instruments and documents or take continue or defend any proceedings which may be required by the Bank or any Receiver pursuant to this deed or the exercise of any of their powers

Appropriation

7.1 Subject to Clause 7.2 the Bank may appropriate all payments received for the account of the Mortgagor in reduction of any part of the Mortgagor's Obligations as the Bank decides

7.2 The Bank may open a new account or accounts upon the Bank receiving actual or constructive notice of any charge or interest affecting the Property the Charged Assets or the Goodwill. Whether or not the Bank opens any such account no payment received by the Bank after receiving such notice shall (if followed by any payment out of or debit to the relevant account) be appropriated towards or have the effect of discharging any part of the Mortgagor's Obligations outstanding at the time of receiving such notice

Preservation of other Security and Rights and Further Assurance

8.1 This deed is in addition to any other security present or future held by the Bank for the Mortgagor's Obligations and shall not merge with or prejudice such other security or any contractual or legal rights of the

Bank

8.2 The Mortgagor will at the Mortgagor's own cost at the Bank's request execute any deed or document and take any action required by the Bank to perfect this security or further to secure the Mortgagor's Obligations on the Property the Charged Assets and the Goodwill

Memorandum and Articles of Association

9 If the Mortgagor is a company the Mortgagor certifies that this deed does not contravene the Mortgagor's Memorandum and Articles of Association

10.1  Any notice or demand by the Bank may be sent by post or fax or delivered
      to the Mortgagor at the Mortgagor's address last known to the Bank or if
      the Mortgagor is a company may be served personally on any director or the
      secretary of the Mortgagor

10.2  A notice or demand by the Bank by post shall be deemed served on the day
      after posting

10.3  A notice or demand by the Bank by fax shall be deemed served at the time
      of sending

Governing Law

11 This deed shall be governed by and construed in accordance with English law

12.1  The expressions "Mortgagor" and "Bank" where the context admits include
      their respective successors in title and assigns

12.2  If two or more persons are included in the expression "Mortgagor" then the
      use in this deed of the word "Mortgagor" shall be deemed to refer to such
      persons both together and separately and the Mortgagor's Obligations shall
      be their joint and several obligations and each of them shall be primarily
      liable by way of indemnity for the liabilities to the Bank of the other or
      others of them

12.3  References to the "Property" and the "Charged Assets" include any part of
      it or them and the "Property" includes all covenants and rights affecting
      or concerning the same. The "Property" also includes any share from time
      to time held by the Mortgagor in any landlord or management company of the
      Property

12.4  Interest will be calculated both before and after demand or judgment on a
      daily basis and compounded according to agreement or in the absence of
      agreement monthly on such days as the Bank may select

12.5  Each of the provisions of this deed shall be severable and distinct from
      one another and if one or more of such provisions is invalid or
      unenforceable the remaining provisions shall not in any way be affected

In Witness of which this deed has been duly executed

/s/ P. Fortune
---------------
Director

/s/ S.J. Cutler
---------------
Secretary/Director

(Please ensure this document is dated)

Signed and Delivered as a deed by the Mortgagor acting by a director and its secretary or two directors

Exhibit 10.5

[LOGO] NatWest Debenture Secs 1 (9/98)

Date:                   17 December 2001

Definitions

Bank:                   National Westminster Bank Plc

Company:                Bottomline Technologies Europe Limited Company No:
                        01911956

Company's               Obligations: All the Company's liabilities to the Bank
                        of any kind and in any currency (whether present or
                        future actual or contingent and whether incurred alone
                        or jointly with another) together with the Bank's
                        charges and commission Interest and Expenses

Expenses:               All expenses (on a full indemnity basis) incurred by the
                        Bank or any Receiver at any time in connection with the
                        Property or Company's Obligations or in taking or
                        perfecting this deed or in preserving defending or
                        enforcing the security created by this deed or in
                        exercising any power under this deed or otherwise with
                        Interest from the date they are incurred

Interest:               Interest at any rate(s) charged to the Company by the
                        Bank from time to time

Property:               The whole and any part of the undertaking property and
                        assets of the Company charged by Clause 1

Registered Land:        Description of property       Land Registry Title Number

Required Currency:      The currency or currencies in which the Company's
                        Obligations are expressed from time to time

Charge

1           The Company covenants to discharge on demand the Company's
            Obligations and as a continuing security for such discharge and with
            full title guarantee charges to the Bank:-

1.1         By way of legal mortgage all the freehold and leasehold property now
            vested in or charged to the Company including any Registered Land

1.2         By way of fixed charge all estates or interests in any freehold and
            leasehold property now and in the future vested in or charged to the
            Company except the property charged by Clause 1.1

1.3         By way of fixed charge all the plant machinery and fixtures and
            fittings of the Company present and future

1.4         By way of fixed charge all furniture furnishings equipment tools and
            other chattels of the Company present and future not regularly
            disposed of in the ordinary course of business

1.5         By way of fixed charge all the goodwill and uncalled capital of the
            Company present and future

1.6         By way of fixed charge all stocks shares and other securities of the
            Company present and future

1.7         By way of fixed charge all intellectual property rights choses in
            action and claims of the Company present and future and the proceeds
            of any insurance from time to time affecting the Property

1.8         By way of fixed charge the benefit of any currency or interest rate
            swap cap or collar or other hedging agreement or any futures
            transaction or treasury instrument made with the Bank or any third
            party

1.9         By way of fixed charge all book debts and other debts of the Company
            present and future and the proceeds of payment or realisation of
            each of them until the receipt of the proceeds from time to time
            into an account in accordance with Clause 4.2

1.10        By way of fixed charge all funds standing to the credit of the
            Company from time to time on any account with the Bank or any other
            bank or financial institution or organisation including all receipts
            from time to time paid into an account in accordance with Clause
            4.2.

1.11        By way of floating charge all the undertaking and all property
            assets and rights of the Company present and future not subject to a
            fixed charge under this deed

Restrictions

2.1         The Company will not without the previous written consent of the
            Bank:-

2.1.1       Create or permit to arise any mortgage charge or lien on the
            Property

2.1.2       Dispose of the Property charged by Clauses 1.1 to 1.10 inclusive

2.1.3       Deal with the Company's book debts and other debts otherwise than by
            collecting them in the ordinary course of the Company's business and
            in particular the Company will not realise its book debts and other
            debts by means of block discounting factoring or the like

2.1.4       Dispose of the Property charged by Clause 1.11 other than in the
            ordinary course of business

2.1.5       Grant or accept a surrender of any lease or license of or part with
            or share possession or occupation of its freehold and leasehold
            property or any part of it

2.2         The Company requests the Chief Land Registrar to enter a restriction
            on the Register of any Registered Land that except under an order of
            the Registrar no disposition by the proprietor(s) of the land is to
            be registered without the consent of the registered proprietor of
            this deed

Insurance

3.1         The Company will keep comprehensively insured to the Bank's
            reasonable satisfaction all of the Property which is of an insurable
            nature for its full reinstatement cost and in default the Bank may
            enter and effect such insurance (without becoming liable to account
            as mortgagee in possession)

3.2         The Company will hold in trust for the Bank all money received under
            any insurance of the Property and at the Bank's option will apply
            the same in making good the relevant loss or damage or in or towards
            discharge of the Company's Obligations

4.1         The Company will from time to time deposit with the Bank all
            insurance policies (or where the Bank agrees copies of them) deeds
            and documents of title relating to the Property

4.2         The Company will pay into the Company's account with the Bank (or
            such other account as the Bank may specify from time to time) all
            money which the Company may receive in respect of the Company's book
            debts and other debts

5.1         The Company will keep the Property charged by Clauses 1.1 to 1.4
            inclusive in good condition and in default the Bank may enter and
            effect repairs (without becoming liable to account as mortgagee in
            possession)

5.2         The Company will not without prior written consent of the Bank make
            any alteration to the Property charged by Clauses 1.1 and 1.2 which
            would require Planning Permission or approval under any Building
            Regulations

6           The Bank may by written notice to the Company convert the floating
            charge into a fixed charge as regards any of the Property specified
            in the notice

Powers of the Bank

7.1         The Bank may without restriction grant or accept surrenders of
            leases of the Company's freehold and leasehold property or any part
            of it

7.2         Section 103 of the Law of Property Act 1925 shall not apply and the
            Bank may exercise its power of sale and other powers under that or
            any other Act or this deed at any time after the date of this deed

7.3         The Bank may under the hand of any official or manager or by deed
            appoint or remove a Receiver or Receivers of the Property and may
            fix and pay the fees of a Receiver but any Receiver shall be deemed
            to be the agent of the Company and the Company shall be solely
            responsible for the Receiver's acts defaults and remuneration

7.4         All or any of the powers conferred on a Receiver by Clause 8 may be
            exercised by the Bank without first appointing a Receiver or
            notwithstanding any appointment

7.5         The Bank will not be liable to account to the Company as mortgagee
            in possession for any money not actually received by the Bank

7.6         Section 93(1) of the Law of Property Act 1925 shall not apply to
            this deed

7.7         In addition to any lien or right to which the Bank may be entitled
            by law the Bank may from time to time without notice and both before
            and after demand set off the whole or any part of the Company's
            Obligations against any deposit or credit balance or any account of
            the Company with the Bank (whether or not that deposit or balance is
            due to the Company)

7.8         Despite any term to the contrary in relation to any deposit or
            credit balance on any account of the Company with the Bank that
            deposit or balance will not be capable of being assigned dealt with
            mortgaged or charged and will not be repayable to the Company before
            all the Company's Obligations have been discharged but the Bank may
            without prejudice to this deed permit the Company to make
            withdrawals from time to time

7.9         The Bank may exchange or convert to the Required Currency and
            currency held or received

Receivers

8.1         Any Receiver appointed by the Bank shall be a Receiver and Manager
            and shall (in addition to all powers conferred on him by law) have
            the following powers which in the case of Joint Receivers may be
            exercised jointly or severally:-

8.1.1       To take possession of and generally manage the Property and any
            business of the Company

8.1.2       To carry out on any freehold or leasehold property of the Company
            any new works or complete any unfinished works of building
            reconstruction maintenance furnishing or equipment

8.1.3       To purchase or acquire any land or other property and purchase
            acquire grant or release any interest in or right over land or the
            benefit of any covenants (positive or restrictive) affecting land

8.1.4       To sell lease surrender or accept surrenders of leases charge or
            otherwise deal with or dispose of the Property without restriction
            including (without limitation) power to dispose of any fixtures
            separately from the land

8.1.5       To carry into effect and complete any transaction by executing deeds
            or documents in the name of or on behalf of the Company

8.1.6       To take continue or defend any proceedings and enter into any
            arrangement or compromise

8.1.7       To insure the Property and any works and effect indemnity insurance
            or other similar insurance and obtain bonds and give indemnities and
            security to any bondsmen

8.1.8       To call up any uncalled capital of the Company with all the powers
            conferred by the Articles of Association of the Company in relation
            to calls

8.1.9       To employ advisers consultants managers agents workmen and others

8.1.10      To purchase or acquire materials tools equipment goods or supplies

8.1.11      To borrow any money and secure the payment of any money in priority
            to the Company's Obligations for the purpose of the exercise of any
            of his powers

8.1.12      To do any other acts which the Receiver may consider to be
            incidental or conducive to any of his powers or to the realisation
            of the Property

8.2         A Receiver shall apply all money he receives first in the repayment
            of all money borrowed by him and his expense and liabilities and in
            payment of his fees and secondly towards the remaining matters
            specified in Section 109(8) of the Law of Property Act 1925

9           The Company irrevocably appoints the Bank and any Receiver severally
            to be the Attorney of the Company (with full power of substitution
            and delegation) in the Company's name and on the Company's behalf
            and as the Company's act and deed to sign or execute all deeds
            instruments and documents or take continue or defend any proceedings
            which may be required by the Bank or any Receiver pursuant to this
            deed or the exercise of any of their powers

Appropriation

10.1        Subject to Clause 10.2 the Bank may appropriate all payments
            received for the account of the Company in reduction of any part of
            the Company's Obligations as the Bank decides

10.2        The Bank may open a new account or accounts upon the Bank receiving
            actual or constructive notice of any charge or interest affecting
            the Property. Whether or not the Bank opens any such account no
            payment received by the Bank after receiving such notice shall (if
            followed by any payment out of or debit to the relevant account) be
            appropriated towards or have the effect of discharging any part of
            the Company's Obligations outstanding at the time of receiving such
            notice

11.1        This deed is in addition to any other security present or future
            held by the Bank for the Company's Obligations and shall not merge
            with or prejudice such other security or any contractual or legal
            rights of the Bank

11.2        The Company will at its own cost at the Bank's request execute any
            deed or document and take any action required by the Bank to perfect
            this security or further to secure on the Property the Company's
            Obligations

12          The Company certifies that this deed does not contravene the
            Company's Memorandum and Articles of Association

Notices

13.1        Any notice or demand by the Bank may be served personally on any
            director or the secretary of the Company or may be sent by post or
            fax or delivered to the Company at the Company's address last known
            to the Bank

13.2        A notice or demand by the Bank by post shall be deemed served on the
            day after posting

13.3        A notice or demand by the Bank by fax shall be deemed served at the
            time of sending

Governing Law

14 This deed shall be governed by and construed in accordance with English Law

15.1        The expressions "Company" and "Bank" where the context admits
            include their respective successors in title and assigns

15.2        Interest will be calculated both before and after demand or judgment
            on a daily basis and compounded according to agreement or in the
            absence of agreement monthly on such days as the Bank may select

15.3        References to the "Property" include any part of it

15.4        References to freehold and leasehold property include all covenants
            and rights-affecting or concerning the same

15.5        Each of the provisions of this deed shall be severable and distinct
            from one another and if one or more of such provisions is invalid or
            unenforceable the remaining provisions shall not in any way be
            affected

In Witness of which this deed has been duly executed

Signed and Delivered as a deed by the Company acting by a director and its secretary or two directors

/s/ P. Fortune
--------------------------------
Director

/s/ S.J. Cutler
--------------------------------
Secretary/Director

(Please ensure the document is dated)


/s/ [ILLEGIBLE]
--------------------------------
Duly  Authorized Official

For and on behalf of the Bank

National Westminster Bank Plc releases to the within named Company the undertaking and other property and assets comprised in the within written document

For and on behalf of National Westminster Bank Plc

Date