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. officer Micheal D. Hill, who serves as CFO, Treasurer and Secretary, reported an insider transaction involving company common stock. On 12/16/2025, 8,856 shares of common stock were disposed of at $1.485 per share with a transaction code "F," indicating shares were withheld by the issuer to satisfy tax withholding obligations tied to the vesting of restricted stock units, rather than sold in the open market.
Following this tax withholding event, Hill beneficially owned 331,222 shares of common stock directly. In addition, 160,042 shares were held indirectly through the MDH Trust, a trust for the benefit of his family for which he serves as trustee.
Upland Software (UPLD) filed its Q3 2025 10-Q, showing smaller losses amid a leaner footprint. Revenue was $50.5M versus $66.7M a year ago as subscription and support fell to $47.7M. Gross profit was $38.8M. Operating income reached $5.3M, helped by lower operating costs, but other expenses (including interest) led to a net loss of $1.1M.
Year to date, divestitures drove a $24.4M loss and $2.5M of intangible impairment. Cash from operations was $18.5M for the nine months, ending cash at $22.8M. The company refinanced with a new $240.0M senior secured term loan maturing 2031 at SOFR (floor 1.5%) + 6.0% (10.3% at quarter-end) and added a $30.0M revolver (undrawn). Long-term debt was $233.8M. Deferred revenue was $66.9M. The Board approved a $10M repurchase plan; 55,597 shares were bought at an average $2.44, leaving $9.9M authorized. Common shares outstanding were 28,891,348 as of November 4, 2025.
Upland Software, Inc. filed a Form 8-K stating it issued a press release announcing financial results for the quarter ended September 30, 2025. The press release is included as Exhibit 99.1 and incorporated by reference.
The filing identifies UPLD common stock listed on The Nasdaq Global Market. The report is dated November 6, 2025 and was signed by the Chief Financial Officer.
Upland Software (UPLD) director D. Chung reported a grant of 25,000 restricted stock units on 10/27/2025 at a stated price of $0. Half of the RSUs vest on 12/16/2025, with the remaining units vesting in two equal installments on 3/16/2026 and 6/16/2026, contingent on continued board service.
After the grant, Chung beneficially owns 124,484 shares directly. Any proceeds from later sales of shares covered by these RSUs will be transferred to HGGC pursuant to an agreement, and Chung disclaims all pecuniary interest in the reported securities.
Upland Software (UPLD) reported an insider equity grant. A director acquired 25,000 restricted stock units on 10/27/2025 at $0. The RSUs vest as follows: one‑half on 12/16/2025, and the remainder in two equal quarterly installments on 3/16/2026 and 6/16/2026. Following this transaction, the director beneficially owned 124,232 shares, held directly.
Upland Software (UPLD) director T. Mattox reported acquiring 25,000 shares of Common Stock via restricted stock units on 10/27/2025 at a price of $0 per share, according to a Form 4.
The RSUs vest as follows: one-half on 12/16/2025, and the remainder in two equal quarterly installments on 3/16/2026 and 6/16/2026.
Following this transaction, Mattox beneficially owned 419,008 shares, held directly.
Upland Software (UPLD) reported an insider equity award on a Form 4. A company director acquired 25,000 shares of common stock in the form of restricted stock units (RSUs) on 10/27/2025 at a stated price of $0 per unit.
The RSUs vest as disclosed: one-half on 12/16/2025, with the remainder vesting in two equal quarterly installments on 3/16/2026 and 6/16/2026. Following this transaction, the reporting person beneficially owned 191,437 shares. The ownership form is listed as Direct.
Upland Software (UPLD) reported an insider equity award. A director acquired 25,000 shares on 10/27/2025 at a reported price of $0, reflecting a grant of restricted stock units. Following the transaction, the director directly beneficially owns 144,490 shares.
The RSUs vest as follows: one-half on 12/16/2025, and the remainder in two equal installments on 3/16/2026 and 6/16/2026.
Upland Software insider J. McDonald reported a tax-withholding disposition of restricted stock units on 09/16/2025. The filing shows 22,956 shares were withheld at an effective price of $2.48; the filer held 2,429,169 shares directly after the transaction and 363,738 shares indirectly through National Financial Services as custodian for J. McDonald. The report clarifies the withheld shares were to satisfy tax obligations and were not an open-market sale. The filing notes an additional 125,000 shares held in a trust for Mr. McDonald’s children are excluded from the reported beneficial ownership. The form is signed by an attorney-in-fact on 09/17/2025.
Upland Software insider sale and tax withholding reported. Michael Douglass Hill, the company's CFO, Treasurer and Secretary, reported a disposition of 11,152 shares of Upland Software common stock on 09/16/2025 at a price of $2.48 per share. The filing states these shares were withheld by the issuer to satisfy tax withholding obligations related to the vesting of restricted stock units and explicitly notes this was not an open-market sale.
After the reported disposition, Mr. Hill directly beneficially owns 340,078 shares and indirectly owns 160,042 shares held in the MDH Trust for his family, for a total of 500,120 shares referenced in the filing.