BOTTOMLINE TECHNOLOGIES INC /DE/
S-3, 2000-11-28
PREPACKAGED SOFTWARE
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<PAGE>
             AS FILED WITH THE SECURITIES AND EXCHANGE COMMISSION
                              ON NOVEMBER 28, 2000

                                                REGISTRATION NO. 333-
================================================================================

                       SECURITIES AND EXCHANGE COMMISSION
                             WASHINGTON, D.C. 20549


                                    FORM S-3
                             REGISTRATION STATEMENT
                                     UNDER
                           THE SECURITIES ACT OF 1933

                                  ----------

                       BOTTOMLINE TECHNOLOGIES (de), INC.
             (Exact Name of Registrant as Specified in its Charter)

                                    DELAWARE
--------------------------------------------------------------------------------
         (State or other Jurisdiction of Incorporation or Organization)

                                   02-0433294
--------------------------------------------------------------------------------
                    (I.R.S. Employer Identification Number)

               155 Fleet Street, Portsmouth, New Hampshire 03801
                                 (603) 436-0700
--------------------------------------------------------------------------------
       (Address, including zip code, and telephone number, including area
               code, of registrant's principal executive offices)

                                Daniel M. McGurl
               Chairman of the Board and Chief Executive Officer
                       Bottomline Technologies (de), Inc.
                                155 Fleet Street
                        Portsmouth, New Hampshire 03801
                                 (603) 436-0700
--------------------------------------------------------------------------------
           (Name, address, including zip code, and telephone number,
                   including area code, of agent for service)

                                With a copy to:
                             John A. Burgess, Esq.
                               Hale and Dorr LLP
                                60 State Street
                          Boston, Massachusetts 02109

     Approximate date of commencement of proposed sale to the public: from time
to time after this Registration Statement becomes effective.

     If the only securities being registered on this form are being offered
pursuant to dividend or interest reinvestment plans, please check the following
box. [_]

     If any of the securities being registered on this form are to be offered on
a delayed or continuous basis pursuant to Rule 415 under the Securities Act of
1933 (the "Securities Act"), other than securities offered only in connection
with dividend or interest reinvestment plans, check the following box. [X]

     If this form is filed to register additional securities for an offering
pursuant to Rule 462(b) under the Securities Act, please check the following box
and list the Securities Act registration statement number of the earlier
effective registration statement for the same offering. [_]

     If this form is a post-effective amendment filed pursuant to Rule 462(c)
under the Securities Act, check the following box and list the Securities Act
registration statement number of the earlier registration statement for the same
offering. [_]

     If delivery of the prospectus is expected to be made pursuant to Rule 434,
please check the following box. [_]
<PAGE>

                         CALCULATION OF REGISTRATION FEE
<TABLE>
<CAPTION>

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

                                                                          Proposed Maximum
     Title of Shares to be          Amount to be      Proposed Maximum       Aggregate           Amount of
          Registered                 Registered      Price Per Share(1)  Offering Price(1)   Registration Fee

<S>                             <C>                      <C>             <C>                 <C>
 Common Stock, $.001 par value    1,137,518 shares         $25.75          $29,291,088.50     $7,732.85
           per share
-------------------------------------------------------------------------------------------------------------------
</TABLE>


(1)  Estimated solely for the purpose of determining the registration fee, in
     accordance with Rule 457 under the Securities Act, based upon the average
     of the reported high and low sales prices of the Common Stock on the Nasdaq
     National Market on November 27, 2000.


     THE REGISTRANT HEREBY AMENDS THIS REGISTRATION STATEMENT ON SUCH DATE OR
DATES AS MAY BE NECESSARY TO DELAY ITS EFFECTIVE DATE UNTIL THE REGISTRANT SHALL
FILE A FURTHER AMENDMENT WHICH SPECIFICALLY STATES THAT THIS REGISTRATION
STATEMENT SHALL THEREAFTER BECOME EFFECTIVE IN ACCORDANCE WITH SECTION 8(A) OF
THE SECURITIES ACT OF 1933 OR UNTIL THE REGISTRATION STATEMENT SHALL BECOME
EFFECTIVE ON SUCH DATE AS THE SECURITIES AND EXCHANGE COMMISSION, ACTING
PURSUANT TO SECTION 8(a), MAY DETERMINE.
<PAGE>

The information in this prospectus is not complete and may be changed.  The
shares are being registered for re-sale not by the Company.  These securities
may not be sold nor may offers to buy these securities be accepted until the
registration statement filed with the Securities and Exchange Commission is
effective.  This prospectus is not an offer to sell these securities, and the
holder of the securities is not soliciting offers to buy these securities in any
state where the offer or sale is not permitted.




PROSPECTUS (Subject to Completion)
Dated November 28, 2000

                       BOTTOMLINE TECHNOLOGIES (de), INC.

                      1,137,518 SHARES OF COMMON STOCK

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

     This prospectus relates to registering for resale shares of common stock
previously issued by Bottomline to the former stockholders of Checkpoint
(Holdings) Limited, a company that Bottomline has acquired.

     The prices at which the selling stockholders identified in this prospectus,
or their pledgees, donees, transferees or other successors-in-interest,
collectively termed the "selling stockholders," may sell the shares registered
hereby will be determined by the prevailing market price for the shares or in
negotiated transactions.  Bottomline will not receive any proceeds from the sale
of the shares.

     Bottomline's common stock is listed on the Nasdaq National Market under the
symbol "EPAY". On November 28, 2000, the last reported sale price of
Bottomline's common stock was $25.00.

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

     INVESTING IN OUR COMMON STOCK INVOLVES A HIGH DEGREE OF RISK.  SEE "RISK
FACTORS" BEGINNING ON PAGE 3.

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

     Neither the Securities and Exchange Commission nor any state securities
commission has approved or disapproved of these securities or passed upon the
adequacy or accuracy of this prospectus.  Any representation to the contrary is
a criminal offense.

                 The date of this Prospectus is ________, 2000.



<PAGE>

                                TABLE OF CONTENTS



PAGE

BOTTOMLINE.........................................   2
RISK FACTORS.......................................   3
SPECIAL NOTE REGARDING FORWARD-LOOKING STATEMENTS..   8
USE OF PROCEEDS....................................   8
SELLING STOCKHOLDERS...............................   9
PLAN OF DISTRIBUTION...............................  13
LEGAL MATTERS......................................  15
EXPERTS............................................  15
WHERE YOU CAN FIND MORE INFORMATION................  16
INCORPORATION BY REFERENCE.........................  16


     No person has been authorized to give any information or to make any
representations other than those contained in this prospectus in connection with
the offering made hereby, and if given or made, such information or
representations must not be relied upon as having been authorized by Bottomline,
the selling stockholders or by any other person. Neither the delivery of this
prospectus nor any sale made hereunder shall, under any circumstances, create
any implication that information herein is correct as of any time subsequent to
the date hereof.

     This prospectus does not constitute an offer to sell or a solicitation of
an offer to buy any security other than the securities covered by this
prospectus, nor does it constitute an offer to or solicitation of any person in
any jurisdiction in which such offer or solicitation may not lawfully be made.





<PAGE>

                                   BOTTOMLINE

     Bottomline's principal executive offices are located at 155 Fleet Street,
Portsmouth, New Hampshire 03801, and our telephone number is (603) 436-0700.
Unless the context otherwise requires, references in this prospectus to
"Bottomline," "the Registrant," "we," "us" and "our" refers to Bottomline
Technologies (de), Inc.


                                       2
<PAGE>

                                  RISK FACTORS

     Investing in our common stock involves a high degree of risk.  You should
carefully consider the risks and uncertainties described below before purchasing
our common stock.  The risks and uncertainties described below are not the only
ones facing our company.  Additional risks and uncertainties may also impair our
business operations.  If any of the following risks actually occur, our
business, financial condition or results of operations would likely suffer.  In
that case, the trading price of our common stock could fall, and you may lose
all or part of the money you paid to buy our common stock.

A SIGNIFICANT PERCENTAGE OF OUR REVENUES TO DATE HAS COME FROM OUR PAYMENT
MANAGEMENT OFFERINGS AND OUR PERFORMANCE WILL DEPEND ON CONTINUED MARKET
ACCEPTANCE OF THESE OFFERINGS

          A significant percentage of our revenues to date has come from the
license and maintenance of our payment management offerings and sales of related
products and services. Any reduction in demand for our payment management
offerings could have a material adverse effect on our business, operating
results and financial condition. Our future performance will depend to a large
degree upon the market acceptance of our payment management offerings as a
payment management solution. Our prospects will also depend upon enterprises
seeking to enhance their payment functions to integrate electronic payment
capabilities. In addition, our future results will depend on the continued
market acceptance of desktop software for use in a departmental setting,
including our laser check printing solutions, as well as our ability to
introduce enhancements to meet the market's evolving needs for secure, payment
management solutions.

OUR FUTURE FINANCIAL RESULTS WILL DEPEND UPON CONTINUED MARKET ACCEPTANCE OF OUR
NETTRANSACT AND BANKQUEST PRODUCTS

          If the NetTransact and BankQuest products that we acquired do not
continue to achieve market acceptance, our future financial results will be
adversely affected. We acquired the NetTransact bill presentment software from
The Northern Trust Company, a financial institution, in July 1999. General
availability of the NetTransact product was announced in February 2000. We
acquired the web-based BankQuest cash management software in our acquisition of
Integrated Cash Management Services, Inc. in October 1999. BankQuest was
commercially introduced in April 2000 and is now generally available. If either
of these products has any unanticipated performance problems or bugs, or does
not enjoy wide commercial success, our long-term business strategy would be
adversely affected.

INTEGRATION OF ACQUISITIONS OR STRATEGIC INVESTMENTS COULD DISRUPT OUR BUSINESS
AND OUR FINANCIAL CONDITION COULD BE HARMED

          We have made acquisitions of companies, including our recent
acquisitions of Checkpoint and Flashpoint, and we may acquire or make
investments in other businesses, products or technologies in the future. Our
acquisitions of Checkpoint and Flashpoint, as well as any other acquisitions or
strategic investments, if any, may entail numerous risks that include the
following:

    .   difficulties in assimilating acquired operations, technologies or
        products;

    .   diversion of management's attention from our core business concerns;

    .   risks of entering markets in which we have no or limited prior
        experience;

    .   substantial dilution of our current stockholders' ownership;

    .   incurrence of substantial debt;

    .   incurrence of significant amortization expenses related to goodwill and
        other intangible assets; and

                                       3
<PAGE>

    .   incurrence of significant immediate write-offs.

Any such difficulties encountered as a result of any mergers or acquisition
could materially affect our business, operating results and financial condition.

WE FACE RISKS ASSOCIATED WITH OUR INTERNATIONAL OPERATIONS THAT COULD HARM OUR
FINANCIAL CONDITION AND RESULTS OF OPERATIONS

    Our future growth rates and success are in part dependent on continued
growth and success in international markets. As is the case with most
international operations, the success and profitability of our international
operations are subject to numerous risks and uncertainties that include the
following:

    .   difficulties and costs of staffing and managing foreign operations;

    .   certification requirements and differing regulatory and industry
        standards;

    .   reduced protection for intellectual property rights in some countries;

    .   fluctuations in currency exchange rates; and

    .   import or export licensing requirements.

WE MUST ATTRACT AND RETAIN HIGHLY SKILLED PERSONNEL WITH KNOWLEDGE OF ELECTRONIC
PAYMENT AND BILL PRESENTMENT TECHNOLOGY AND THE BANKING INDUSTRY

    We are dependent upon the ability to attract, hire, train and retain highly
skilled technical, sales and marketing, and support personnel, particularly with
expertise in electronic payment and bill presentment technology and knowledge of
the banking industry. Competition for qualified personnel is intense. In
addition, our corporate headquarters location in Portsmouth, New Hampshire may
limit our access to skilled personnel. Any failure to attract, hire or retain
qualified personnel could have a material adverse effect on our business,
operating results and financial condition. In addition, we plan to expand our
sales and marketing and product development organizations. Based on our
experience, it takes an average of nine months for a salesperson to become fully
productive. We cannot assure you that we will be successful in increasing the
productivity of our sales personnel, and the failure to do so could have a
material adverse effect on our business, operating results and financial
condition.

OUR FIXED COSTS MAY LEAD TO FLUCTUATIONS IN OPERATING RESULTS IF OUR REVENUES
ARE BELOW EXPECTATIONS, AND IF OUR OPERATING RESULTS ARE BELOW EXTERNAL
EXPECTATIONS, THE MARKET PRICE OF OUR COMMON STOCK MAY FALL

    A significant percentage of our expenses, particularly personnel costs and
rent, are relatively fixed, and based in part on expectations of future
revenues. We may be unable to reduce spending in a timely manner to compensate
for any significant fluctuations in revenues. Accordingly, shortfalls in
revenues may cause significant fluctuations in operating results in any quarter.
Quarterly operating results that are below the expectations of public market
analysts could adversely affect the market price for our common stock. Factors
that could cause these fluctuations include the following:

   .   the timing of orders and longer sales cycles, particularly due to any
   increase in average selling prices of our software solutions;

   .   the timing and market acceptance of new products or product enhancements
   by either us or our competitors;

    .   the timing of product implementations, which are highly dependent on
    customers' resources and discretion;

                                       4
<PAGE>

    .   the incurrence of costs relating to the integration of software products
    and operations in connection with acquisitions of technologies or
    businesses;

    .   delivery interruptions relating to equipment and supplies purchased from
    third-party vendors, which could delay system sales; and

    .   economic conditions which may affect our customers' and potential
    customers' budgets for technological expenditures.

Because of these factors, we believe that period to period comparisons of our
results of operations are not necessarily meaningful.

THE MARKET PRICE OF OUR COMMON STOCK HAS EXPERIENCED, AND MAY CONTINUE TO BE
SUBJECT TO, EXTREME PRICE AND VOLUME FLUCTUATIONS

  Stock markets, in general, and The Nasdaq Stock Market in particular, have
experienced extreme price and volume fluctuations. Broad market fluctuations of
this type may adversely affect the market price of our common stock.

  The market price of our common stock has experienced, and may continue to be
subject to extreme fluctuations due to a variety of factors, including:

 .   public announcements concerning us, our competitors or our industry;

 .   fluctuations in operating results;

 .   introductions of new products or services by us or our competitors;

 .   adverse developments in patent or other proprietary rights;

 .   changes in analysts' earnings estimates;

 .   announcements of technological innovations by our competitors; and

 .   general and industry-specific business, economic and market conditions

OUR SUCCESS DEPENDS ON OUR ABILITY TO DEVELOP NEW AND ENHANCED SOFTWARE,
SERVICES AND RELATED PRODUCTS

  The bill presentment, payment and cash management software markets in which we
compete are subject to rapid technological change and our success is dependent
on our ability to develop new and enhanced software, services and related
products that meet our evolving market needs. Trends which could have a critical
impact on us include:

 .   rapidly changing technology that could require us to make our products
compatible with new database or network systems;

 .   evolving industry standards and mandates, such as those mandated by the
National Automated Clearing House Association, the Association for Payment
Clearing Services and the Debt Collection Improvement Act of 1996; and

 .   developments and changes relating to the Internet that we must address as
we introduce new products.


 If we are unable to develop and introduce new products, or enhancements to
 existing products, in a timely and successful manner, our business, operating
 results and financial condition could be materially adversely affected.

 OUR SUCCESS DEPENDS ON THE WIDE-SPREAD ADOPTION OF THE INTERNET AND GROWTH OF
 ELECTRONIC BUSINESS

     Our future success will in large part depend upon the willingness of
 businesses and financial institutions to adopt the Internet as a medium of e-

                                       5
<PAGE>

 business. These entities will probably accept this new medium only if the
 Internet provides substantially greater efficiency and enhances their
 competitiveness. There are critical issues involved in the commercial use of
 the Internet which are not yet fully resolved, including concerns regarding the
 Internet's:

 .   security;

 .   reliability;

 .   ease of access; and

 .   quality of services.

To the extent that any of these issues inhibit or limit the adoption of the
Internet as a medium of e-commerce, our business prospects could be adversely
affected. If electronic business does not continue to grow or grows more slowly
than expected, demand for our products and services may be reduced.

IF THE INTERNET INFRASTRUCTURE IS NOT ADEQUATELY MAINTAINED, THE DEMAND FOR OUR
PRODUCTS AND SERVICES MAY DECREASE

  Our future success will depend, in part, on the maintenance of the Internet
infrastructure. To the extent that the Internet continues to experience
increased numbers of users, frequency of use or increased bandwidth requirements
of users, the Internet infrastructure may not continue to support the demands
placed on it and, as a result, the performance or reliability of the Internet
may be adversely affected. In addition, the Internet could lose its viability as
a form of media due to delays in the development or adoption of new standards
and protocols that can handle increased levels of activity. The infrastructure
and complementary products and services necessary to maintain the Internet as a
viable communications and commercial medium may not be developed or maintained.
Any failure in performance or reliability of the Internet could adversely affect
the demand for our products and services and, consequently, adversely affect our
operating results.

INCREASED GOVERNMENT REGULATION AND LEGAL UNCERTAINTIES MAY IMPAIR THE GROWTH OF
THE INTERNET AND DECREASE DEMAND FOR OUR PRODUCTS AND SERVICES

The laws governing the Internet remain largely unsettled, even in areas where
there has been some legislative action. It may take years to determine whether
and how existing laws, including those governing intellectual property, privacy,
libel and taxation, apply to the Internet generally and to e-commerce in
particular. Legislation could limit the growth in the use of the Internet
generally and decrease the acceptance of the Internet as a communications and
commercial medium, which may decrease demand for our products and services and
thus have a material adverse effect on our business, operating results and
financial condition.

OUR BUSINESS CAN BE ADVERSELY AFFECTED BY PROBLEMS WITH THIRD-PARTY HARDWARE
THAT WE RESELL

  Any problems with third-party hardware that we resell could harm our customer
relationships, industry credibility and financial condition. In a prior fiscal
year, we experienced a significant problem with a third-party printer that we
were then reselling which had a material adverse effect on our operating
results. Any repetition of these or similar problems with third party hardware
could have a material adverse effect on our business, operating results and
financial condition.

INCREASED COMPETITION MAY RESULT IN PRICE REDUCTIONS AND DECREASED DEMAND FOR
OUR PRODUCTS AND SERVICES

  The market for bill presentment, payment and cash management software is
intensely competitive and characterized by rapid technological change. Growing
competition may result in price reductions of our products and services, reduced
revenues and gross margins and loss of market share, any one of which could have

                                       6
<PAGE>

a material adverse effect on our business, operating results and financial
condition. Some competitors in our market have longer operating histories,
significantly greater financial, technical, marketing and other resources,
greater brand recognition and a larger installed customer base than we do. In
addition, current and potential competitors may make strategic acquisitions or
establish cooperative relationships to expand their product offerings and to
offer more comprehensive solutions. We also expect to face additional
competition as other established and emerging companies enter the market for
payment management solutions.

RAPID GROWTH COULD STRAIN OUR PERSONNEL, SYSTEMS AND CONTROLS

  In the past, rapid growth has strained our managerial and other resources. Our
ability to manage any future growth will depend in part on our ability to
continue to enhance our operating, financial and management information systems.
We cannot assure you that our personnel, systems and controls will be adequate
to support any future growth. If we are not able to manage growth effectively,
should it occur, the quality of our services, our ability to retain key
personnel and our business, operating results and financial condition could be
materially adversely affected.

WE DEPEND ON A FEW KEY EMPLOYEES WHO ARE SKILLED IN E-COMMERCE, PAYMENT AND BILL
PRESENTMENT METHODOLOGY AND INTERNET AND OTHER TECHNOLOGIES

Our success depends upon the efforts and abilities of our executive officers
and key technical employees who are skilled in e-commerce, payment methodology
and regulation, and Internet, database and network technologies. We currently do
not maintain "key man" life insurance policies on any of our employees. While
some of our executive officers have employment agreements with us, the loss of
the services of any of our executive officers or other key employees could have
a material adverse effect on our business, operating results and financial
condition.

UNDETECTED BUGS IN OUR SOFTWARE COULD ADVERSELY AFFECT THE PERFORMANCE OF OUR
SOFTWARE AND DEMAND FOR OUR PRODUCTS

  Our software products could contain errors or "bugs" that we have not been
able to detect which could adversely affect their performance and reduce demand
for our products. Any defects or errors in new products, such as NetTransact or
BankQuest, or enhancements could harm our customer relationships and result in
negative publicity regarding us and our products, which could have a material
adverse effect on our business, operating results and financial condition.

OUR BUSINESS COULD BE SUBJECT TO PRODUCT LIABILITY CLAIMS

  Because our software and hardware products are designed to provide critical
payment management, invoicing and cash management functions, we may be subject
to significant product liability claims. Our insurance may not be sufficient to
cover us against these claims or may not be available at all. A product
liability claim brought against us, even if not successful, could require us to
spend significant time and money in litigation. As a result, any such claim,
whether successful or not, could seriously damage our reputation and harm our
business, operating results and financial condition.

OUR BUSINESS COULD BE ADVERSELY AFFECTED IF WE ARE UNABLE TO PROTECT OUR
PROPRIETARY TECHNOLOGY

  We rely upon a combination of patent, copyright and trademark laws and non-
disclosure and other intellectual property contractual arrangements to protect
our proprietary rights. However, we cannot assure you that our patents, pending
applications that may be issued in the future, or other intellectual property
will be of sufficient scope and strength to provide meaningful protection of our
technology or any commercial advantage to us, or that the patents will not be
challenged, invalidated or circumvented. We enter into agreements with our
employees and clients that seek to limit and protect the distribution of
proprietary information. We cannot assure you that the steps we have taken to
protect our intellectual property rights will be adequate to deter

                                       7
<PAGE>

misappropriation of proprietary information, and we may not be able to detect
unauthorized use and take appropriate steps to enforce our intellectual property
rights.

WE COULD BECOME SUBJECT TO LITIGATION REGARDING INTELLECTUAL PROPERTY RIGHTS,
WHICH COULD SERIOUSLY HARM OUR BUSINESS

  In recent years, there has been significant litigation in the United States
involving patents and other intellectual property rights. We may be a party to
litigation in the future to protect our intellectual property or as a result of
an alleged infringement of the intellectual property of others. These claims
could require us to spend significant sums in litigation, pay damages, delay
product installments, develop non-infringing intellectual property or acquire
licenses to intellectual property that is the subject of the infringement claim.
These claims could have a material adverse effect on our business, operating
results and financial condition.

WE MAY INCUR SIGNIFICANT COSTS FROM CLASS ACTION LITIGATION DUE TO THE EXPECTED
VOLATILITY OF OUR COMMON STOCK

     In the past, companies that have experienced volatility in the market price
of their stock have been the object of securities class action litigation. If we
were the object of securities class action litigation, we could incur
substantial costs and experience a diversion of our management's attention and
resources and such securities class action litigation could have a material
adverse effect on our business, financial condition and results of operations.

THE FUTURE SALE OF SHARES OF OUR COMMON STOCK MAY NEGATIVELY AFFECT OUR STOCK
PRICE

     If our stockholders sell substantial amounts of our common stock, including
shares issuable upon the exercise of outstanding warrants and options to
purchase a total of 3,060,127 shares of our common stock as of November 24,
2000, the market price of our common stock could fall. These sales also might
make it more difficult for us to sell equity securities in the future at a time
and price that we deem appropriate.

               SPECIAL NOTE REGARDING FORWARD-LOOKING STATEMENTS

     This prospectus contains forward-looking statements that involve
substantial risks and uncertainties.  In some cases you can identify these
statements by forward-looking words such as "anticipate," "believe," "could,"
"estimate," "expect," "intend," "may," "should," "will," and "would" or similar
words.  You should read statements that contain these words carefully because
they discuss future expectations, contain projections of future results of
operations or of financial position or state other "forward-looking"
information.  The important factors listed above in the section captioned "Risk
Factors," as well as any cautionary language in this prospectus, provide
examples of risks, uncertainties and events that may cause our actual results to
differ materially from the expectations described in these forward-looking
statements.  You should be aware that the occurrence of the events described in
these risk factors and elsewhere in this prospectus could have an adverse effect
on our business, results of operations and financial position.

     Any forward-looking statements in this prospectus are not guarantees of
future performance, and actual results, developments and business decisions may
differ from those envisaged by such forward-looking statements, possibly
materially. We disclaim any duty to update any forward-looking statements, all
of which are expressly qualified by the statements in this section.

                                 USE OF PROCEEDS

     We will not receive any proceeds from the sale of the shares by the selling
stockholders.

     The selling stockholders will pay any selling commissions and expenses
incurred by them for brokerage, accounting or tax services or other expenses

                                       8
<PAGE>

incurred by the selling stockholders in disposing of their shares (other than
the reasonable fees and expenses of counsel for selling stockholders who were
not employees of Checkpoint (Holdings) Limited at the time we acquired that
company) as well as any transfer taxes on the shares that they sell. We will
bear all other costs, fees and expenses incurred in effecting the registration
of the shares covered by this prospectus, including, without limitation, all
registration and filing fees, Nasdaq listing fees, fees and expenses of our
counsel, fees of our accountants, blue sky fees and expenses and reasonable fees
and expenses of counsel for selling stockholders who were not employees of
Checkpoint (Holdings) Limited at the time we acquired that company.

                              SELLING STOCKHOLDERS

     The shares of common stock covered by this prospectus consist of 1,137,518
shares of common stock issued in connection with our acquisition Checkpoint
(Holdings) Limited on August 28, 2000.

     The following table sets forth the number of shares beneficially owned by
the selling stockholders. Beneficial ownership is calculated based on
requirements of the Securities and Exchange Commission and is not necessarily
indicative of beneficial ownership for any other purpose. Peter Fortune is Chief
Executive and a director of our wholly-owned subsidiary Checkpoint (Holdings)
Limited, a company incorporated in England and Wales. Stephen Cutler is Finance
Director of Checkpoint (Holdings) Limited. Aside from these relationships, and
the relationships set forth in the table below, the selling stockholders have
not had a material relationship with Bottomline within the past three years
other than as a result of the ownership of the shares described in the table
below. No estimate can be given as to the amount of shares covered by this
prospectus that will be held by the selling stockholders after completion of
this offering because the selling stockholders may offer all or some of the
shares and because there currently are no agreements, arrangements or
understandings with respect to the sale of any of the shares. However, for
purposes of this table, we have assumed that, after completion of the offering,
none of the shares covered by this prospectus will be held by the selling
stockholders. The shares offered by this prospectus may be offered from time to
time by the selling stockholders named below.

<TABLE>
<CAPTION>

                                            Number of Shares       Number of Shares               Percent of Outstanding
       Name of Selling Stockholders       Registered for Sale    Beneficially Owned as          Shares of Common Stock as
                                               Hereby (1)        of November 24, 2000 (2)        of November 24, 2000 (%)

<S>                                             <C>                      <C>                              <C>
  Andrew Colin McCallum***                      79,520                   114,972 (3)                         *

  Catherine McCallum+                            5,336                   114,972 (3)                         *

  Danielle McCallum+                               853                   114,972 (3)                         *

  Oliver Glenn**                                   853                   114,972 (3)                         *

  Andrew Colin McCallum and Catherine              853                   114,972 (3)                         *
  McCallum as Trustees of Charlotte
  McCallum++

  Andrew Colin McCallum and Catherine              853                   114,972 (3)                         *
  McCallum as Trustees of Ashleigh
  Glenn++

  Richard McCallum+                                853                   114,972 (3)                         *

  Christopher Wilson Peck***                    13,875                    22,267 (4)                         *

  Tracy Jane Peck**                              3,201                    22,267 (4)                         *

  Rowan Nominees Limited c/o Mercury           777,010                 1,056,649 (5)                        7.6
  Asset Management Limited
</TABLE>
                                       9
<PAGE>

<TABLE>
<S>                                       <C>                    <C>                      <C>
  Rowan Nominees Limited a/c RR c/o              56,979                1,056,649 (5)                 *
  Mercury Asset Management Limited

  Peter Kenneth Rooke***                         62,494                   95,269 (6)                 *

  Pamela Rooke+                                   6,912                   95,269 (6)                 *

  Peter Kenneth Rooke and Pamela Rooke            2,304                   95,269 (6)                 *
  as Trustees of Thomas Penn Rooke++

  Simon Thomas Peter Rooke+                       2,303                   95,269 (6)                 *

  James Daniel Wood                               2,303                    3,004                     *

  Peter Stanley Fortune+++                       27,393                   44,531 (7)                 *

  Joanne Barbara Fortune+                         5,336                   44,531 (7)                 *

  Peter Stanley Fortune and Joanne                  711                   44,531 (7)                 *
  Barbara Fortune as Trustees of
  Harriet Joanne Louise Fortune++
</TABLE>

                                      10

<PAGE>

<TABLE>

<S>                                             <C>                      <C>                       <C>
  Peter Stanley Fortune and Joanne                 711                           44,531 (7)          *
  Barbara Fortune as Trustees of James
  Peter Matthew Fortune++

  Stephen Joseph Cutler***+++                    9,605                           16,700 (8)          *

  Kathryn Elizabeth Cutler+                      3,201                           16,700 (8)          *

  John A. Clarke***                             12,807                           16,700              *

  John Christopher Shore**                       3,329                            4,342              *

  Sharon Taylor**                                2,049                            2,672              *

  Kevin Michael Hart**                           2,049                            2,672              *

  Paul John Fannon**+++                          4,098                            8,239 (9)          *

  Timothy Roger John Miller**                    2,049                            2,672              *

  Simon Turley**                                 2,049                            2,672              *

  Stewart James Miller**                         2,049                            2,672              *

  Nigel Kevin Savory**+++                        6,318                            8,239              *

  David Graham Campion**                           853                            1,113              *

  Martin John Weller**                             853                            1,113              *

  Simon Morton**                                   853                            1,113              *

  Ian George Whitney**                             597                              779              *

  Simon David Josephs**                            597                              779              *

  Robert Bailey**                                  597                              779              *

  Edward Charles Adshead-Grant**                   853                            1,113              *

  Paul Lee Simpson**                               597                              779              *

  Ian Frank Armstrong**                            597                              779              *

  Simon John Huntley**                             597                              779              *

  Keith William Adams**                            515                              672              *

  Margaret Luzanycia**                           1,543                            2,013              *

  Steven Andrew Crosson-Smith**                    782                            1,021              *

  Michael Hassan**                                 683                              891              *

  Sally Joy Bailey**                               142                              186              *

  Alistair Ian McQuade**                           597                              779              *

  Paul Christopher Gordon**                        142                              186              *

  Simon Collinson**                                597                              779              *

  Alister James Humphreys**                        597                              779              *
</TABLE>

                                      11
<PAGE>

<TABLE>

<S>                                             <C>                      <C>                       <C>
  Edward Pryor**                                  142                               186              *

  Richard James Harris**                          597                               779              *

  Peter John Dale**                               142                               186              *

  Anthony Steven White**                          355                               464              *

  Ian Raymond Wheeler**                           597                               779              *

  Nathan Jackson**                                177                               232              *

  Richard Alan Dewar**                            177                               232              *

  Ryan Jackson**                                  177                               232              *

  Douglas Wilkinson**                             427                               557              *

  Lisa Kathryn Jackson**                          177                               232              *

  Paul Candahar Nott**                            142                               185              *

  Ian Greville Jones**                            142                               185              *

  Andrew Peter Ryan**                             142                               185              *

  Philip Taylor**                                 427                               557              *

  Patrick Lawrence Reeves**                       142                               185              *

  Peter Michael Phillips**                        142                               185              *

  Richard Gordon Machin**                         142                               185              *

  David Charles Jewell**                          355                               464              *

  Richard David Hatton**                          142                               186              *

  Michelle Lees**                                  89                               116              *

  Julie Mary McGuire**                            142                               186              *

  Kerry Elizabeth Jones**                         142                               186              *

  Candace Melanie Pridgeon**                      142                               186              *

  Ceri Elizabeth Hancox**                          89                               116              *

  Zoe Ann Kirby**                                  89                               116              *

  Carlos Hugh Esperanca**                         107                               140              *

  Clive Kenneth Griffiths**                       107                               140              *

  Mark John Overton**                             107                               140              *

  Andrew Tather**                                 107                               140              *

  Richard Alan Baldock**                          107                               140              *

  Tim Ager**                                       89                               116              *

  Philip David Charnick**                         142                               186              *

  Benjamin Toby Clacy**                            89                               116              *

</TABLE>

                                      12
<PAGE>

<TABLE>

<S>                                             <C>                      <C>                       <C>
  Elaine Duncan**                                 142                               186              *

  Harvey Durrant**                                142                               186              *

  Janet Edwina Mary Hester**                      142                               186              *

  Wayne Jones**                                   142                               186              *

  James Richard Malyon**                          542                               707              *

  Alexis McArdle**                                142                               186              *

  Richard Anthony Parry**                         355                               464              *

  Gareth Rory Priest**                            597                               779              *

  Andrew James Scarborough**                       89                               116              *

  Matthew Andrew Shaw**                            89                               116              *

  Anthony James Skinner**                         427                               557              *

  Christopher John Conway***                   12,807                            16,700              *

  Wendy Crosson Smith*                            427                               557              *

  Anna Elizabeth Webb**                           115                               150              *

  Vanda Jane Fannon**+                          2,220                             8,239 (9)          *
  _________________________
</TABLE>
  *     Less than one percent.
  **    Employed by Checkpoint either currently or within the past three years.
  ***   Former director of Checkpoint or one of its subsidiaries and employed by
        Checkpoint either currently or within the past three years.
  +     Immediate family member of individual(s) employed by Checkpoint either
        currently or within the past three years.
  ++    Trustee has been employed by Checkpoint within the past three years.
  +++   Current director of Checkpoint or one of its subsidiaries.
  (1)   This registration statement also shall cover any additional shares of
        common stock which become issuable in connection with the shares
        registered for sale hereby by reason of any stock split, stock dividend
        or similar transaction.
  (2)   Includes 100,000 shares of common stock issuable pursuant to common
        stock purchase warrants that are currently exercisable.
  (3)   Includes (a) 102,449 shares held by Andrew Colin McCallum, (b) 6,958
        shares held by Catherine McCallum, (c) 1,113 shares held by Danielle
        McCallum, (d) 1,113 shares held by Oliver Glenn, (e) 1,113 shares held
        by Andrew Colin McCallum and Catherine McCallum as Trustees of Charlotte
        McCallum, (f) 1,113 shares held by Andrew Colin McCallum and Catherine
        McCallum as Trustees of Ashleigh McCallum and (g) 1,113 shares held by
        Richard McCallum. The selling stockholder disclaims beneficial ownership
        of such shares other than those held by the selling stockholder (other
        than any shares held by the selling shareholder as trustee).
  (4)   Includes (a) 18,092 shares held by Christopher Wilson Peck and (b) 4,175
        shares held by Tracy Jane Peck. The selling stockholder disclaims
        beneficial ownership of such shares other than those held by the selling
        stockholder.
  (5)   Includes (a) 984,481 shares held by Rowan Nominees Limited c/o Mercury
        Asset Management Limited and (b) 72,168 shares held by Rowan Nominees
        Limited a/c RR c/o Mercury Asset Management Limited. The selling
        stockholder disclaims beneficial ownership of such shares other than
        those held by the selling stockholder.
  (6)   Includes (a) 80,247 shares held by Peter Kenneth Rooke, (b) 9,013 shares
        held by Pamela Rooke, (c) 3,005 shares held by Peter Kenneth Rooke and
        Pamela Rooke as Trustees of Thomas Penn Rooke, and (d) 3,004 shares held
        by Simon Thomas Peter Rooke. The selling stockholder disclaims
        beneficial ownership of such shares other than those held by the selling
        stockholder (other than any shares held by the selling shareholder as
        trustee).
  (7)   Includes (a) 35,719 shares held by Peter Stanley Fortune, (b) 6,958
        shares held by Joanne Barbara Fortune, (c) 927 shares held by Peter
        Stanley Fortune and Joanne Barbara Fortune as Trustees of Harriet Joanne
        Louise Fortune and (d) 927 shares held by Peter Stanley Fortune and
        Joanne Barbara Fortune as Trustees of James Peter Matthew Fortune. The
        selling stockholder disclaims beneficial ownership of such shares other
        than those held by the selling stockholder (other than any shares held
        by the selling shareholder as trustee).
  (8)   Includes (a) 12,525 shares held by Stephen Joseph Cutler and (b) 4,175
        shares held by Kathryn Elizabeth Cutler. The selling stockholder
        disclaims beneficial ownership of such shares other than those held by
        the selling stockholder.
  (9)   Includes (a) 5,344 shares held by Paul John Fannon and (b) 2,895 shares
        held by Vanda Jane Fannon.

                              PLAN OF DISTRIBUTION

     The selling stockholders may sell the shares covered by this prospectus
from time to time.  The term "selling stockholders" includes pledgees, donees,
transferees or other successors-in-interest selling the shares covered by this
prospectus received from a selling stockholders as a gift, partnership
distribution or other non-sale-related transfer after the date of this
prospectus.  The selling stockholders will act independently of us in making
decisions with respect to the timing, manner and size of each sale.

     The sales of the shares may be made on one or more exchanges or in the
over-the-counter market or otherwise, at prices and at terms then prevailing or
at prices related to the then current market price, or in negotiated
transactions.  The selling stockholders may effect such transactions by selling
the shares covered by this prospectus to or through broker-dealers or directly
to purchasers (in the event of a private sale).  The shares may be sold by one
or more of, or a combination of, the following:

     .  a block trade in which the broker-dealer so engaged will attempt to sell
        the shares as agent but may position and resell a portion of the block
        as principal to facilitate the transaction,

                                      13
<PAGE>

     .  purchases by a broker-dealer as principal and resale by such broker-
        dealer for its account pursuant to this prospectus,

     .  an over-the-counter distribution in accordance with the rules of the
        Nasdaq National Market,

     .  ordinary brokerage transactions and transactions in which the broker
        solicits purchasers, and

     .  in privately negotiated transactions.

     To the extent required, this prospectus may be amended or supplemented from
time to time to describe a specific plan of distribution.  In effecting sales,
broker-dealers engaged by the selling stockholders may arrange for other broker-
dealers to participate in the resales.

     The selling stockholders may enter into hedging transactions with broker-
dealers in connection with distributions of the shares or otherwise.  In such
transactions, broker-dealers may engage in short sales of the shares in the
course of hedging the positions they assume with the selling stockholders.  The
selling stockholders may also sell shares short and redeliver the shares to
close out such short positions. The selling stockholders may enter into option
or other transactions with broker-dealers which require the delivery to the
broker-dealer of the shares. The broker-dealer may then resell or otherwise
transfer such shares pursuant to this prospectus. The selling stockholders also
may loan or pledge the shares to a broker-dealer. The broker-dealer may sell the
shares so loaned, or upon a default the broker-dealer may sell the pledged
shares pursuant to this prospectus.

     Broker-dealers or agents may receive compensation in the form of
commissions, discounts or concessions from the selling stockholders.  Broker-
dealers or agents may also receive compensation from the purchasers of the
shares for whom they act as agents or to whom they sell as principals, or both.
Usual and customary brokerage fees will be paid by the selling stockholders.
Broker-dealers or agents and any other participating broker-dealers or the
selling stockholders may be deemed to be "underwriters" within the meaning of
Section 2(11) of the Securities Act in connection with sales of the shares.
Accordingly, any such commission, discount or concession received by them and
any profit on the resale of the shares purchased by them may be deemed to be
underwriting discounts or commissions under the Securities Act.  Because the
selling stockholders may be deemed to be "underwriters" within the meaning of
Section 2(11) of the Securities Act, the selling stockholders will be subject to
the prospectus delivery requirements of the Securities Act. In addition, any
securities covered by this prospectus which qualify for sale pursuant to Rule
144 promulgated under the Securities Act may be sold under Rule 144 rather than
pursuant to this prospectus.

     The selling stockholders may sell the shares only through registered or
licensed brokers or dealers if required under applicable state securities laws.
In addition, in certain states the shares may not be sold unless they have been
registered or qualified for sale in the applicable state or an exemption from
the registration or qualification requirement is available and is complied with.

     Under applicable rules and regulations under the Exchange Act, any person
engaged in the distribution of the shares may not simultaneously engage in
market making activities with respect to Bottomline's common stock for a
specified period prior to the commencement of such distribution.  In addition,
the selling stockholders will be subject to applicable provisions of the
Exchange Act and the associated rules and regulations under the Exchange Act,
including Regulation M, which provisions may limit the timing of purchases and
sales of shares of our common stock by the selling stockholders.  Bottomline
will make copies of this prospectus available to the selling stockholders and
has informed the selling stockholders of the need for delivery of copies of this
prospectus to purchasers at or prior to the time of any sale of the shares.

     Bottomline will file a supplement to this prospectus, if required, pursuant

                                      14
<PAGE>

to Rule 424(b) under the Securities Act upon being notified by a selling
stockholder that any material arrangement has been entered into with a broker-
dealer for the sale of shares through a block trade, special offering, exchange
distribution or secondary distribution or a purchase by a broker or dealer.
Such supplement will disclose:

     .  the name of the selling stockholder and of the participating broker-
        dealer(s),

     .  the number of shares involved,

     .  the price at which such shares were sold,

     .  the commissions paid or discounts or concessions allowed to such broker-
        dealer(s), where applicable,

     .  that such broker-dealer(s) did not conduct any investigation to verify
        the information set out or incorporated by reference in this prospectus,
        and

     .  other facts material to the transaction.

     The selling stockholders will bear all underwriting discounts and selling
commissions, if any, attributable to the sales of the shares.  The selling
stockholders may agree to indemnify any broker-dealer or agent that participates
in transactions involving sales of the shares against certain liabilities,
including liabilities arising under the Securities Act.  Nevada Bond Investment
Corp. II has agreed to indemnify certain persons, including underwriters,
against certain liabilities in connection with the offering of the shares,
including liabilities arising under the Securities Act.

     We have agreed with the selling stockholders to keep the registration
statement of which this prospectus constitutes a part effective until the
earlier of (i) August 28, 2002 and (ii) the date the shares covered by this
prospectus have been sold pursuant to such registration statement.

                                  LEGAL MATTERS

     The validity of the common stock being offered has been passed upon for us
by Hale and Dorr LLP, Boston, Massachusetts.

                                     EXPERTS

     The consolidated financial statements and schedule of Bottomline
Technologies (de), Inc. appearing in Bottomline Technologies (de), Inc.'s annual
report (Form 10-K) for the year ended June 30, 2000 have been audited by Ernst &
Young LLP, independent auditors, as set forth in their report thereon included
therein and incorporated herein by reference. Such financial statements and
schedule are incorporated herein by reference in reliance upon such report given
on the authority of such firm as experts in accounting and auditing.

     The financial statements of Flashpoint, Incorporated as of and for the year
ended December 31, 1999 appearing in Bottomline Technologies (de), Inc.'s
Current Report on Form 8-K/A, dated November 13, 2000, have been audited by
Ernst & Young LLP, independent auditors, as set forth in their report thereon
included therein and incorporated herein by reference.  Such financial
statements are incorporated herein by reference in reliance upon such report
given on the authority of such firm as experts in accounting and auditing.


     The consolidated financial statements of Checkpoint (Holdings) Limited as
of April 30, 2000 and 1999 and for the year ended April 30, 2000 and the period
January 11, 1999 (inception) to April 30, 1999 and Checkpoint Security Services
Limited for the period May 1, 1998 to March 10, 1999 appearing in Bottomline
Technologies (de), Inc.'s Current Report on Form 8-K/A, dated November 13, 2000,
have been audited by Ernst & Young, independent auditors, as set forth in their
report thereon included therein and incorporated herein by reference. Such

                                      15

<PAGE>

financial statements are incorporated herein by reference in reliance upon such
report given on the authority of such firm as experts in accounting and
auditing.

     The financial statements of Checkpoint Security Services Limited for the
year ended April 30, 1998 appearing in Bottomline Technologies (de), Inc.'s
Current Report on Form 8-K/A, dated November 13, 2000, have been audited by
Smith & Williamson, independent auditors, as set forth in their report thereon
included therein and incorporated herein by reference. Such financial statements
are incorporated herein by reference in reliance upon such report given on the
authority of such firm as experts in accounting and auditing.

                       WHERE YOU CAN FIND MORE INFORMATION

     We file annual, quarterly, and special reports, proxy statements, and other
information with the SEC.  You can read our Securities and Exchange Commission
filings, including the registration statement, over the Internet at the
Securities and Exchange Commission 's web site at HTTP://WWW.SEC.GOV.  You may
also read and copy any document we file with the Securities and Exchange
Commission at its public reference facilities at 450 Fifth Street, N.W.,
Washington, D.C. 20549.  You may also obtain copies of the documents at
prescribed rates by writing to the Public Reference Section of the Securities
and Exchange Commission at 450 Fifth Street, N.W., Washington, D.C. 20549.
Please call the Securities and Exchange Commission at 1-800-SEC-0330 for further
information on the operation of the public reference facilities.

     This prospectus is part of a registration statement that we filed with the
Securities and Exchange Commission. The registration statement contains more
information than this prospectus regarding us and our common stock, including
certain exhibits and schedules. You can obtain a copy of the registration
statement from the Securities and Exchange Commission at the address listed
above or from its Internet web site.

                           INCORPORATION BY REFERENCE

     The Securities and Exchange Commission allows us to "incorporate by
reference" certain information we file with them, which means that we can
disclose important information to you by referring you to those documents.  We
incorporate by reference the documents listed below and any future filings made
by us with the Securities and Exchange Commission under Sections 13(a), 13(c),
14 or 15(d) of the Exchange Act until the selling stockholders sell all of the
securities that we have registered in this prospectus.  Information that we file
later with the Securities and Exchange Commission will automatically update and
supersede this information.

     We have incorporated by reference into this prospectus the following
documents we filed with the Securities and Exchange Commission:

     (i)   the Annual Report on Form 10-K for the fiscal year ended June 30,
           2000,

     (ii)  the Quarterly Report on Form 10-Q for the quarter ended September 30,
           2000,

     (iii) the Current Report on Form 8-K filed on September 12, 2000, as
           amended by a Form 8-K/A filed on November 13, 2000, and

     (iv)  the description of the common stock contained in our Registration
           Statement on Form 8-A dated January 12, 1999.

     You may request a copy of these filings, at no cost, by writing or
telephoning us at the following address: Bottomline Technologies (de), Inc., 155
Fleet Street, Portsmouth, New Hampshire 03801, (603) 436-0700.

                                      16

<PAGE>

PART II. INFORMATION NOT REQUIRED IN PROSPECTUS

ITEM 14. OTHER EXPENSES OF ISSUANCE AND DISTRIBUTION

     The following table sets forth the various expenses to be incurred by us in
connection with the registration of the securities being registered hereby, all
of which will be borne by us except any underwriting discounts and commissions
and expenses incurred by the selling stockholders for brokerage, accounting or
tax services or any other expenses incurred by the selling stockholders in
disposing of the shares (other than the reasonable fees and expenses of counsel
for selling stockholders who were not employees of Checkpoint (Holdings) Limited
at the time we acquired that company).

SEC Registration Fee           $ 7,732.85

Accounting Fees and Expenses..     10,000

Legal Fees and Expenses.......     10,000

Transfer Agent Fees...........          0

Printing Fees.................      1,000

Miscellaneous Expenses........          0
                               ----------

Total......................... $28,732.85

- - *All fees are estimates


ITEM 15. INDEMNIFICATION OF DIRECTORS AND OFFICERS


     Article EIGHTH of the Registrant's Amended and Restated Certificate of
Incorporation (the "Restated Certificate of Incorporation") provides that no
director of the Registrant shall be personally liable for any monetary damages
for any breach of fiduciary duty as a director, except to the extent that the
Delaware General Corporation Law prohibits the elimination or limitation of
liability of directors for breach of fiduciary duty.

     Article NINTH of the Registrant's Restated Certificate of Incorporation
provides that a director or officer of the Registrant (a) shall be indemnified
by the Registrant against all expenses (including attorneys' fees), judgments,
fines and amounts paid in settlement incurred in connection with any litigation
or other legal proceeding (other than an action by or in the right of the
Registrant) brought against him by virtue of his position as a director or
officer of the Registrant if he acted in good faith and in a manner he
reasonably believed to be in, or not opposed to, the best interests of the
Registrant, and, with respect to any criminal action or proceeding, had no
reasonable cause to believe his conduct was unlawful and (b) shall be
indemnified by the Registrant against all expenses (including attorneys' fees)
and amounts paid in settlement incurred in connection with any action by or in
the right of the Registrant brought against him by virtue of his position as a
director or officer of the Registrant if he acted in good faith and in a manner
he reasonably believed to be in, or not opposed to, the best interests of the
Registrant, except that no indemnification shall be made with respect to any
matter as to which such person shall have been adjudged to be liable to the
Registrant, unless a court determines that, despite such adjudication but in
view of all of the circumstances, he is entitled to indemnification of such
expenses. Notwithstanding the foregoing, to the extent that a director or
officer has been successful, on the merits or otherwise, including, without
limitation, the dismissal of an action without prejudice, he is required to be
indemnified by the Registrant against all expenses (including attorneys' fees)
incurred in connection therewith. Expenses shall be advanced to a director or
officer at his request, provided that he undertakes to repay the amount advanced
if it is ultimately determined that he is not entitled to indemnification for
such expenses.

                                     II-1
<PAGE>

     Indemnification is required to be made unless the Registrant determines
that the applicable standard of conduct required for indemnification has not
been met. In the event of a determination by the Registrant that the director or
officer did not meet the applicable standard of conduct required for
indemnification, or if the Registrant fails to make an indemnification payment
within 60 days after such payment is claimed by such person, such person is
permitted to petition the court to make an independent determination as to
whether such person is entitled to indemnification.  As a condition precedent to
the right of indemnification, the director or officer must give the Registrant
notice of the action for which indemnity is sought and the Registrant has the
right to participate in such action or assume the defense thereof.

     Article NINTH of the Registrant's Restated Certificate of Incorporation
further provides that the indemnification provided therein is not exclusive, and
provides that in the event that the Delaware General Corporation Law is amended
to expand the indemnification permitted to directors or officers the Registrant
must indemnify those persons to the fullest extent permitted by such law as so
amended.

     Section 145 of the Delaware General Corporation Law provides that a
corporation has the power to indemnify a director, officer, employee or agent of
the corporation and certain other persons serving at the request of the
corporation in related capacities against amounts paid and expenses incurred in
connection with an action or proceeding to which he is or is threatened to be
made a party by reason of such position, if such person shall have acted in good
faith and in a manner he reasonably believed to be in or not opposed to the best
interests of the corporation, and, in any criminal proceeding, if such person
had no reasonable cause to believe his conduct was unlawful; provided that, in
the case of actions brought by or in the right of the corporation, no
indemnification shall be made with respect to any matter as to which such person
shall have been adjudged to be liable to the corporation unless and only to the
extent that the adjudicating court determines that such indemnification is
proper under the circumstances.  The Registrant has entered into letter
agreements with certain of its officers and directors confirming its undertaking
to provide indemnification as contemplated by Section 145 under certain
circumstances.


ITEM 16. EXHIBITS
<TABLE>
<CAPTION>



Exhibit No.                                              Description
------------------  -------------------------------------------------------------------------------------
<S>                <C>
            2.1*    Share Purchase Agreement between the Persons named in column (A) of Schedule 1 thereto and
                    Bottomline Technologies (de), Inc. dated August 28, 2000

            4.1**   Amended and Restated Certificate of Incorporation of the Registrant

            4.2**   Amended and Restated By-laws of the Registrant

            4.3**   Specimen Certificate for Shares of Common Stock, $.001 par  value per share, of the
                    Registrant

            5.1     Opinion of Hale and Dorr LLP

           23.1     Consent of Ernst & Young LLP

           23.2     Consent of Ernst & Young

           23.3     Consent of Smith & Williamson

           23.4     Consent of Hale and Dorr LLP (included in the opinion of Hale and Dorr LLP filed in
                    Exhibit 5.1 hereto)
</TABLE>
________________

*     Incorporated herein by reference to the Registrant's Current Report on
      Form 8-K dated September 12, 2000 (File No. 000-25259).

                                     II-2
<PAGE>

**    Incorporated herein by reference to the Registrant's Registration
      Statement on Form S-1, as amended (File No. 333-67309).


ITEM 17. UNDERTAKINGS

     The undersigned registrant hereby undertakes:

     (4) to file, during any period in which offers or sales are being made, a
post-effective amendment to this registration statement: (i) to include any
prospectus required by Section 10(a)(3) of the Securities Act; (ii) to reflect
in the prospectus any facts or events arising after the effective date of the
registration statement, or the most recent post-effective amendment thereof,
which, individually or in the aggregate, represent a fundamental change in the
information set forth in the registration statement; and (iii) to include any
material information with respect to the plan of distribution not previously
disclosed in the registration statement or any material change to such
information in the registration statement.

     (5) That, for the purpose of determining any liability under the Securities
Act, each such post-effective amendment shall be deemed to be a new registration
statement relating to the securities offered therein, and the offering of such
securities at that time shall be deemed to be the initial bona fide offering
thereof.

     (6) To remove from registration by means of a post-effective amendment any
of the securities being registered which remain unsold at the termination of the
offering.

     Insofar as indemnification for liabilities arising under the Securities Act
may be permitted to directors, officers and controlling persons of the
registrant pursuant to the foregoing provisions or otherwise, the registrant has
been advised that in the opinion of the Securities and Exchange Commission such
indemnification is against public policy as expressed in the Securities Act and
therefore is unenforceable.  In the event that a claim for indemnification
against such liabilities, other than the payment by the registrant of expenses
incurred or paid by a director, officer or controlling person of the registrant
in the successful defense of any action, suit or proceeding is asserted by such
director, officer or controlling person in connection with the securities being
registered, the registrant will, unless in the opinion of its counsel the matter
has been settled by controlling precedent, submit to a court of appropriate
jurisdiction the question whether such indemnification by it is against public
policy as expressed in the Securities Act and will be governed by the final
adjudication of such issue.

     The undersigned registrant hereby undertakes that, for purposes of
determining any liability under the Securities Act, each filing of the
registrant's annual report pursuant to Section 13(a) or Section 15(d) of the
Exchange Act, and, where applicable, each filing of an employee benefit plan's
annual report pursuant to Section 15(d) of the Exchange Act, that is
incorporated by reference in the registration statement shall be deemed to be a
new registration statement relating to the securities offered therein, and the
offering of such securities at that time shall be deemed to be the initial bona
fide offering thereof.

                                     II-3
<PAGE>

                                    SIGNATURE

     Pursuant to the requirements of the Securities Act of 1933, as amended, the
Registrant certifies that it has reasonable grounds to believe that it meets all
the requirements for filing on Form S-3 and has duly caused this Registration
Statement to be signed on its behalf by the undersigned, thereunto duly
authorized, in the City of Portsmouth, State of New Hampshire, as of this 28th
day of November, 2000.

                                   BOTTOMLINE TECHNOLOGIES (de), INC.
                                    (Registrant)

                                   By:
                                      /s/ Daniel M. McGurl
                                   -------------------------------
                                   Daniel M. McGurl
                                   Chairman of the Board
                                   and Chief Executive Officer


                        POWER OF ATTORNEY AND SIGNATURES

     We, the undersigned officers and directors of Bottomline Technologies (de),
Inc., hereby severally constitute Daniel M. McGurl, Robert A. Eberle and John A.
Burgess, Esq., and each of them singly, our true and lawful attorneys with full
power to them, and each of them singly, to sign for us and in our names in the
capacities indicated below, the registration statement on Form S-3 filed
herewith and any and all subsequent amendments to said registration statement,
and generally to do all such things in our names and behalf in our capacities as
officers and directors to enable Bottomline Technologies (de), Inc. to comply
with the provisions of the Securities Act of 1933, as amended, and all
requirements of the Securities and Exchange Commission, hereby ratifying and
confirming our signatures as they may be signed by our said attorneys, or any of
them, to said Registration Statement and any and all amendments thereto.

     Pursuant to the requirements of the Securities Act of 1933, as amended,
this Registration Statement has been signed by the following persons in the
capacities and on the dates indicated.



<TABLE>
<CAPTION>
Signature                                Title                                  Date
---------                                -----                                  ----
<S>                                      <C>                                   <C>
  /s/ Daniel M. McGurl                   Chairman of the Board and Chief        November 28, 2000
------------------------------           Executive Officer (Principal
Daniel M. McGurl                         Executive Officer)



  /s/ Joseph L. Mullen                   President, Chief Operating Officer     November 28, 2000
------------------------------           and Director
Joseph L. Mullen
</TABLE>

                                     II-4
<PAGE>

<TABLE>

<S>                                      <C>                                   <C>
  /s/ Robert A. Eberle                   Executive Vice President, Chief        November 28, 2000
------------------------------           Financial Officer, Treasurer and
Robert A. Eberle                         Director (Principal Financial and
                                         Accounting Officer)

  /s/ James L. Loomis                    Director                               November 28, 2000
------------------------------
James L. Loomis

  /s/ Joseph L. Barry, Jr.               Director                               November 28, 2000
------------------------------
Joseph L. Barry, Jr.

  /s/ Dianne Gregg                       Director                               November 28, 2000
------------------------------
Dianne Gregg

  /s/ James W. Zilinski                  Director                               November 28, 2000
------------------------------
James W. Zilinski

</TABLE>

                                     II-5
<PAGE>

EXHIBIT INDEX

<TABLE>
<CAPTION>


Exhibit No.                                   Description
------------------  ------------------------------------------------------------------------------
<S>                 <C>
            2.1*    Share Purchase Agreement between the Persons named in column (A) of Schedule 1
                    thereto and Bottomline Technologies (de), Inc. dated August 28, 2000

            4.1**   Amended and Restated Certificate of Incorporation of the Registrant

            4.2**   Amended and Restated By-laws of the Registrant

            4.3**   Specimen Certificate for Shares of Common Stock, $.001 par value per
                    share, of the Registrant

            5.1     Opinion of Hale and Dorr LLP

           23.1     Consent of Ernst & Young LLP

           23.2     Consent of Ernst & Young

           23.3     Consent of Smith & Williamson

           23.4     Consent of Hale and Dorr LLP (included in the opinion of Hale and Dorr LLP
                    filed in Exhibit 5.1 hereto)

</TABLE>
________________

*   Incorporated herein by reference to the Registrant's Current Report on Form
    8-K dated September 12, 2000 (File No. 000-25259).
**  Incorporated herein by reference to the Registrant's Registration Statement
    on Form S-1, as amended (File No. 333-67309).



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