Press release

Upland Software Announces Pricing of Public Offering of Common Stock

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Upland Software, Inc. (Nasdaq: UPLD) (“Upland”), a leader in cloud-based
Enterprise Work Management software, today announced the pricing of an
underwritten public offering of 3,300,000 shares of common stock at a
price to the public of $42.00 per share. The aggregate offering size,
before deducting the underwriting discounts and commissions and other
offering expenses, is expected to be approximately $138,600,000. The
offering is expected to close on or about May 13, 2019, subject to
customary closing conditions. In addition, the underwriters have been
granted a 30-day option to purchase up to an additional 495,000 shares
of common stock at the public offering price, less the underwriting
discounts and commissions.

Credit Suisse and Jefferies are acting as active book running managers
for the offering. Canaccord Genuity and Needham & Company are acting as
passive book running managers. William Blair, Craig-Hallum Capital
Group, Raymond James, Roth Capital Partners and SunTrust Robinson
Humphrey are acting as co-managers for the offering. The offering is
subject to market and other conditions, and there can be no assurance
that the offering will be completed.

A shelf registration statement relating to the shares of common stock
offered in the public offering described above was filed with the
Securities and Exchange Commission (“SEC”) on December 12, 2018 and
declared effective by the SEC on January 31, 2019. A preliminary
prospectus supplement relating to the offering has been filed with the
SEC and is available on the SEC’s website at
Copies of the final prospectus supplement, when available, may be
obtained from Credit Suisse Securities (USA) LLC; By mail: Attn:
Prospectus Department, Eleven Madison Avenue, 3rd floor, New York, NY
10010; By phone: 1-800-221-1037; By e-mail:
or Jefferies LLC, Attn: Equity Syndicate Prospectus Departments, 520
Madison Avenue, 2nd Floor, New York, NY 10022, by telephone at
877-821-7388 or by email at

This press release does not constitute an offer to sell or the
solicitation of an offer to buy, nor shall there be any offer,
solicitation or sale of these securities in any state or jurisdiction in
which such offer, solicitation or sale would be unlawful prior to
registration or qualification under the securities laws of any such
state or jurisdiction.

About Upland Software, Inc.

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

Forward-looking Statements

This release contains “forward-looking statements” within the meaning of
Section 27A of the Securities Act, and Section 21E of the Securities
Exchange Act of 1934, as amended. Forward-looking statements generally
relate to future events or our future financial or operating
performance, including our proposed offering, and are subject to
substantial risks, uncertainties and assumptions. We may not actually
achieve the plans, intentions, or expectations disclosed in our
forward-looking statements. Our forward-looking statements do not
reflect the potential impact of any future acquisitions, mergers,
dispositions, joint ventures, or investments we may make. 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
“believe,” “expect,” “anticipate,” “intend,” “plan,” “estimate,” “seek,”
“will,” “may,” “hope,” “predict,” “could,” “should,” “would,” “project,”
or the negative or plural of these words or similar expressions,
although not all forward-looking statements contain these words. Actual
results may differ materially from those indicated by such
forward-looking statements as a result of various important factors,
including, but are not limited to: the completion of the public
offering; the satisfaction of customary closing conditions related to
the proposed public offering; and the impact of general economic,
industry or political conditions in the United States or
internationally. These and other risks are described in greater detail
under the caption “Risk Factors” included in Upland’s Annual Report on
Form 10-K for the year ended December 31, 2018 filed with the SEC on
March 15, 2019, under the caption “Risk Factors” included in the
preliminary prospectus supplement to be filed in relation to the
offering described above, and other filings Upland may make with the SEC
in the future. 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, except as required by law. 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