UPLD Upland Software Inc.

Upland Software Announces Pricing of Public Offering of its Common Stock

Upland Software, Inc. (Nasdaq: UPLD), a leader in cloud-based tools for digital transformation, today announced the pricing of an underwritten public offering of 3,500,000 shares of common stock at a price to the public of $34.00 per share. The aggregate offering size, before deducting the underwriting discounts and commissions and other offering expenses, is expected to be $119,000,000. The offering is expected to close on or about August 14, 2020, subject to customary closing conditions. The underwriters for the offering will also have a 30-day option to purchase up to an additional 525,000 shares of common stock at the public offering price, less the underwriting discounts and commissions.

Upland intends to use the net proceeds of the offering to continue its acquisition strategy and for general corporate purposes.

Credit Suisse is acting as lead book-running manager for the offering. Jefferies, Canaccord Genuity and Needham & Company are acting as book-running managers. Craig-Hallum Capital Group, Raymond James, Roth Capital Partners, and William Blair are acting as co-managers for the offering.

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 August 10, 2020 and became effective immediately upon its filing. 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, 6933 Louis Stephens Drive, Morrisville, North Carolina 27560; By phone: 1-800-221-1037; By e-mail: .

This press release does not constitute an offer to sell or the solicitation of an offer to buy these securities, 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

Upland Software (Nasdaq: UPLD) is a leader in cloud-based tools for digital transformation. The Upland Cloud enables thousands of organizations to engage with customers on key digital channels, optimize sales team performance, manage projects and IT costs, and automate critical document workflows. As of the date of this release, Upland has more than 10,000 customers with over 1,000,000 users across a broad range of industries, including financial services, retail, technology, manufacturing, legal, education, consumer goods, media, telecommunications, government, non-profit, food and beverage, healthcare and life sciences. The Upland Cloud is backed by a 100% customer success commitment and the UplandOne platform, which puts customers at the center of everything Upland does. To learn more, visit .

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 guidance related to future performance, 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: our ability to complete the offering of common stock and the use of proceeds therefrom, our ability to satisfy the customary closing conditions related to the offering; our financial performance and our ability to achieve, sustain or increase profitability or predict future results; our ability to attract and retain customers; our ability to deliver high-quality customer service; the growth of demand for enterprise work management applications; our plans regarding, and our ability to effectively manage, our growth; our plans regarding future acquisitions and our ability to consummate and integrate acquisitions; maintaining our senior management and key personnel; our ability to maintain and expand our direct sales organization; our ability to obtain financing in the future on acceptable term or at all; 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; the operation and reliability of our third-party data centers and other service providers; our ability to adapt to technological change and continue to innovate; the anticipated impact on our business of the COVID-19 pandemic and related public health measures; our ability to integrate our applications with other software applications; and our ability to comply with privacy laws and regulations. These and other risks are described in greater detail under the caption "Risk Factors" included in our (i) Annual Report on Form 10-K for the year ended December 31, 2019 filed with the SEC on March 2, 2020, (ii) Quarterly Report on Form 10-Q for the quarter ended June 30, 2020 filed with the SEC on August 7, 2020, and (iii) preliminary prospectus supplement filed with the SEC on August 10, 2020 in relation to the offering described above, and other filings we may make with the SEC in the future. Additional information will also be set forth in Upland's future quarterly reports on Form 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, 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 release.

EN
12/08/2020

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