Press release

Upland Software Acquires PostUp, Raises Guidance

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Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based enterprise
work management software, has acquired PostUp, a leading provider of
email and audience development solutions for publishing and media
brands. PostUp is an important addition to Upland’s Customer Experience
Management (CXM) solution suite. The acquisition adds approximately $11
million in annualized revenues and will be immediately accretive to
Upland’s Adjusted EBITDA per share.

“PostUp adds deep market expertise, sophisticated audience development
solutions, and an established customer base in media and publishing to
our CXM solution suite,” said Jack McDonald, chairman and CEO of Upland
Software. “Moreover, the transaction is immediately accretive to
Adjusted EBITDA per share and takes Upland to a $205 million annualized
revenue run rate. As this transaction demonstrates, our acquisition
pipeline is robust, and we are actively pursuing additional
opportunities to build out our solution suites.”

PostUp’s sophisticated email and audience development solutions help
companies in the media and publishing sector to develop and grow their
audiences, drive deeper audience engagement, and monetize their
communications channels by generating new advertising and subscription
revenue streams.

“We are thrilled to welcome PostUp’s customers and team members to
Upland,” said Jed Alpert, Upland’s Executive Vice President and General
Manager of CXM Solutions. “PostUp’s market leading capabilities
establish audience identity through email capture, browser push, and
actionable insights from integration with Google Analytics data to
create hyper-targeted audience segments. This powerful technology will
benefit current Upland CXM customers, as well as add to our growing
media and publishing verticals.”

The purchase price paid for PostUp was $35.0 million in cash at closing,
net of cash acquired. Upland expects the acquisition to generate annual
revenue of approximately $11.0 million, of which $10.8 million is
recurring, subject to reductions for a deferred revenue discount as a
result of GAAP purchase accounting, estimated as inconsequential for the
remainder of 2019. The acquisition is within Upland’s target price range
of 5-8x pro forma Adjusted EBITDA and will generate at least $5.0
million in Adjusted EBITDA annually once fully integrated. For the
remaining stub period of the quarter ending June 30, 2019, Upland
expects PostUp to contribute approximately $2.1 million of total revenue
and approximately $0.4 million of Adjusted EBITDA as Upland integrates
PostUp into model. The acquisition will be immediately accretive to
Upland’s Adjusted EBITDA per share.

In conjunction with this acquisition, $30.0 million of new term debt was
drawn and $10 million of revolver debt was drawn, taking Upland’s gross
debt outstanding from $281.4 million to $321.4 million with debt, net of
cash on hand, now at approximately $307 million at a maximum interest
rate of LIBOR + 400 basis points (currently at approximately 6.5%).

Business Outlook

Upland today also announced that it has raised its full year 2019
guidance to reflect the PostUp acquisition, raising revenue, recurring
revenue, and Adjusted EBITDA guidance ranges. The increase in 2019
revenue guidance below is net of an inconsequential reduction for a
deferred revenue discount as a result of GAAP purchase accounting and
all guidance adjustments are prorated for an effective closing date of
April 18, 2019.

For the full year ending December 31, 2019, Upland expects reported
total revenue to be between $202.4 and $206.4 million, including
subscription and support revenue between $189.2 and $192.4 million, for
growth in recurring revenue of 39.7% at the mid-point over the year
ended December 31, 2018. Adjusted EBITDA is expected to be between $73.7
and $76.1 million, representing growth of 41.0% at the mid-point over
the year ended December 31, 2018. The transaction will be immediately
accretive to Upland’s Adjusted EBITDA per share.

About Upland Software

Upland Software (Nasdaq: UPLD) is a leader in cloud-based enterprise
work management software. Upland provides seven enterprise cloud
solution suites that enable more than one million users at over 9,000
accounts to win and engage customers, automate business operations,
manage projects and IT costs, and share knowledge throughout the
enterprise. All of Upland’s solutions are backed by a 100% customer
success commitment and the UplandOne platform, which puts customers at
the center of everything we do. To learn more, visit

About PostUp

PostUp is a leading provider of email and audience development
technology and services to the publishing and media industries. With a
proven services team, award-winning platform, and hand-picked partners,
PostUp delivers personalized communications that drive engagement and
increase revenues. To learn more, visit

The CoSine Group acted as exclusive financial advisor to PostUp.

Notes & Forward-looking Statements

Annualized revenues exclude the impact of deferred revenue discount
associated with GAAP purchase accounting. This release contains
forward-looking statements, which are subject to substantial risks,
uncertainties and assumptions. Accordingly, you should not place undue
reliance on these forward-looking statements. Forward-looking statements
include any statement that does not directly relate to any historical or
current fact and often include words such as “target,” “believe,”
“expect,” “anticipate,” “intend,” “plan,” “estimate,” “seek,” “will,”
“may” or similar expressions. Actual results may differ materially from
those indicated by such forward-looking statements as a result of
various important factors, including: our financial performance and our
ability to achieve, sustain or increase profitability or predict
financial results; our ability to attract and retain customers; our
ability to deliver high-quality customer service; lack of demand growth
for enterprise work management applications; our ability to effectively
manage our growth; our ability to consummate and integrate acquisitions
and mergers; our ability to maintain our senior management and key
personnel; our ability to maintain and expand our direct sales
organization; the performance of our resellers; our ability to adapt to
changing market conditions and competition; our ability to successfully
enter new markets and manage our international expansion; fluctuations
in currency exchange rates; the operation and reliability of our
third-party data centers and other service providers; and factors that
could affect our business and financial results identified in Upland’s
filings with the Securities and Exchange Commission (the “SEC”),
including Upland’s most recent annual report on Form 10-K filed with the
SEC. Additional information will also be set forth in Upland’s future
quarterly reports on Forms 10-Q, annual reports on Form 10-K, and other
filings that Upland makes with the SEC. The forward-looking statements
herein represent Upland’s views as of the date of this press release and
these views could change. However, while Upland may elect to update
these forward-looking statements at some point in the future, Upland
specifically disclaims any obligation to do so. These forward-looking
statements should not be relied upon as representing the views of Upland
as of any date subsequent to the date of this press release.

Non-GAAP Financial Measures

To supplement our consolidated financial statements, which are prepared
and presented in accordance with GAAP, we use non-GAAP financial
measures including Adjusted EBITDA.

We use non-GAAP financial measures for financial and operational
decision-making and as a means to evaluate period-to-period comparisons.
Our management believes that non-GAAP financial measures provide
meaningful supplemental information regarding our performance and
liquidity by excluding certain expenses and expenditures that may not be
indicative of our recurring core business operating results, such as our
revenues excluding the impact for foreign currency fluctuations or our
operating performance excluding not only non-cash charges, but also
discrete cash charges that are infrequent in nature. We believe that
both management and investors benefit from referring to non-GAAP
financial measures in assessing our performance and when planning,
forecasting, and analyzing future periods. Non-GAAP financial measures
also facilitate management’s internal comparisons to our historical
performance and liquidity as well as comparisons to our competitors’
operating results. We believe non-GAAP financial measures are useful to
investors both because they allow for greater transparency with respect
to key metrics used by management in its financial and operational
decision-making, and they are used by our institutional investors and
the analyst community to help them analyze the health of our business.

Upland defines Adjusted EBITDA as net income (loss), calculated in
accordance with GAAP, plus net income (loss) from discontinued
operations, depreciation and amortization expense, interest expense,
net, other expense (income), net, provision for income taxes,
stock-based compensation expense, acquisition-related expenses,
non-recurring litigation costs, and purchase accounting adjustments for
deferred revenue.

For a reconciliation of non-GAAP financial measures to the most directly
comparable GAAP financial measures, please see Upland’s earnings press
releases filed on Forms 8-K with the SEC and on the Investor Relations
section of Upland’s website at We are
unable to reconcile any forward-looking non-GAAP financial measures to
their directly comparable GAAP financial measures because the
information which is needed to complete a reconciliation is unavailable
at this time without unreasonable effort.