Upland Software's SEC filings document a cloud software issuer focused on AI-powered knowledge and content management applications. Recent Form 8-K reports furnish quarterly results and guidance, correct annual-report materials, disclose Nasdaq listing-compliance notices, changes in the independent registered public accounting firm, and chief executive transition and compensation arrangements.
Proxy materials cover annual meeting matters, board governance, executive compensation, equity awards, and pay-versus-performance disclosures. The filings also frame the company's capital structure through common stock and preferred stock purchase rights, while operating disclosures tie revenue and cash-flow measures to subscription and support software operations and completed divestitures.
Upland Software, Inc. (UPLD) reported that officer Dan Doman, Chief Operating & Product Officer, had 2,952 shares of common stock withheld on September 16, 2026 to satisfy tax withholding obligations related to vesting restricted stock units. This was not an open market sale. After this withholding, Doman directly holds 86,473 shares of Upland common stock.
Upland Software, Inc. (UPLD) reported that CEO and President Nathaniel Sean had 1,640 shares of common stock withheld on September 16, 2026 to satisfy tax withholding obligations upon vesting of restricted stock units. The shares were withheld by the issuer and were not an open market sale. Following this transaction, Sean directly held 48,574 shares of Upland Software common stock. No transactions were made under a Rule 10b5-1 trading plan.
Upland Software, Inc. (UPLD) reported that its Chief Financial Officer Jennifer L. Simon had 1,117 shares of common stock withheld on September 16, 2026 to satisfy tax withholding obligations related to vesting of restricted stock units. After this withholding, she directly holds 28,883 shares of Upland common stock. The company notes this was not an open market sale of securities.
Upland Software, Inc. (symbol: UPLD) is the issuer of record for a Form 4 filing submitted to the SEC.
Upland Software, Inc. (UPLD) reported that Jennifer L. Simon, its Chief Financial Officer, filed an initial insider ownership statement as a reporting person. The filing lists no reportable transactions or equity holdings at this time, serving as a baseline disclosure of her status as an officer.
Upland Software, Inc. reported declining revenue and a significantly larger loss for the quarter ended June 30, 2026. Total revenue was $49.1 million, down 8% year over year, with subscription and support revenue falling 9% to $46.2 million as divested product lines and Sunset Assets continued to roll off.
Profitability weakened sharply due to a non-cash goodwill impairment of $35.2 million, driving a quarterly net loss of $35.3 million and a basic and diluted net loss per share of $12.53. For the first six months, revenue declined 16% to $97.8 million and net loss was $36.5 million. Despite this, Adjusted EBITDA remained positive at $12.8 million for the quarter and $25.5 million year to date, and operating cash flow was $11.0 million in the first half.
The balance sheet shows $356.6 million in total assets, including $222.7 million of goodwill, against $223.8 million of senior secured term debt and a total stockholders’ deficit of $89.8 million. Upland also has $136.7 million in Series A preferred liquidation preference plus accrued dividends. After quarter-end, Nasdaq notified the company that its market value of publicly held shares was below the $15 million minimum, giving Upland until January 27, 2027 to regain compliance.
Upland Software reported second quarter 2026 total revenue of $49.1 million, down 8% from $53.4 million a year earlier, mainly due to 2025 divestitures. Subscription and support revenue was $46.2 million, down 9%. Professional services contributed $1.3 million.
GAAP results showed a net loss of $35.3 million, wider than the $13.0 million loss in 2025, driven largely by a non-cash goodwill impairment of $35.2 million. By contrast, non-GAAP net income rose 18% to $6.6 million. Adjusted EBITDA was $12.8 million, or 26% of revenue, versus $13.6 million and a 25% margin a year earlier. Operating cash flow improved to $5.4 million, with free cash flow of $5.3 million and cash on hand of $31.0 million.
For third quarter 2026, Upland guides total revenue to $45.7–$48.7 million and Adjusted EBITDA to $11.9–$13.4 million, with margin expected at 27% versus 32% in the prior-year quarter. For full year 2026, it expects revenue of $190.1–$196.1 million, down 11% at the midpoint from 2025, and Adjusted EBITDA of $49.8–$52.8 million, a 12% decline at the midpoint, with a 27% margin matching 2025.
Upland Software, Inc. director Timothy Mattox reported selling 847.4 shares of common stock on 2026-08-07 in an open market or private transaction at a weighted average price of $4.2801 per share. The sale was made under an approved Rule 10b5-1 trading plan adopted on 03/09/2026, and his directly held stake after the sale was 36,052.6 shares.
Upland Software, Inc. director Timothy Mattox reported a sale of 1,000 shares of common stock on 2026-08-06 at $4.27 per share in an open-market or private transaction. After this sale, he holds 36,900 shares directly. The transaction was conducted under an approved Rule 10b5-1 trading plan with an adoption date of 03/09/2026.
UPLD filed a notice of proposed sale of common stock. Timothy Mattox, using Morgan Stanley Smith Barney LLC Executive Financial Services, plans to sell 848 shares of common stock on NASDAQ on 08/07/2026. The shares relate to restricted stock originally issued on 12/16/2018. The filing also lists several prior sales of 1,000 shares each during late July and early August 2026.