Upland Software, Inc.: insider trades · United States · SEC (Form 4)

About Upland Software, Inc.

Upland Software, Inc. is a U.S.-based software company listed on the Nasdaq stock market in the United States, with headquarters in Austin, Texas. The company has been built through a long-running acquisition strategy, assembling a portfolio of cloud software assets that are designed to improve enterprise productivity, knowledge access, customer support workflows, and document-centric operations. In its recent communications, Upland describes itself as a leader in AI-powered knowledge and content management software, positioning the company around enterprise search, knowledge delivery, proposal management, and related workflow automation use cases. ([investor.uplandsoftware.com](https://investor.uplandsoftware.com/news/news-details/2026/New-Upland-BA-Insight-Platform-Delivers-Integrated-AI-Search-Experiences-for-Enterprises/default.aspx?utm_source=openai)) Upland was founded in 2010 by Jack McDonald. Since then, its growth model has relied heavily on acquiring complementary software businesses and integrating them into a broader B2B platform. That strategy has shaped Upland’s market identity: it is not a single-product vendor, but rather a roll-up style software operator with multiple niche offerings that address specific operational pain points inside large organizations. In 2026, Jack McDonald stepped down from the CEO role while remaining chairman of the board, marking an important governance transition for the company. ([investor.uplandsoftware.com](https://investor.uplandsoftware.com/news/news-details/2026/Upland-Announces-Commencement-of-New-CEO-Tenure-and-Inducement-Awards/default.aspx?utm_source=openai)) The company’s core product set spans knowledge management, enterprise search, proposal and RFP automation, customer service enablement, and cloud fax and related communications tools. Key brands include Upland BA Insight, Upland Panviva, Upland RightAnswers, Upland Qvidian, and Upland InterFAX. These offerings help customers organize institutional knowledge, improve access to trusted content, accelerate proposal generation, and support frontline service teams. A major strategic theme in 2025 and 2026 has been the incorporation of AI capabilities, including conversational search and broader AI-enhanced knowledge experiences. ([investor.uplandsoftware.com](https://investor.uplandsoftware.com/news/news-details/2026/New-Upland-BA-Insight-Platform-Delivers-Integrated-AI-Search-Experiences-for-Enterprises/default.aspx?utm_source=openai)) From a competitive standpoint, Upland operates in a crowded and fragmented enterprise software landscape, competing with point-solution vendors as well as larger software suites. Its advantage is less about category dominance and more about specialized functionality, vertical relevance, and the ability to cross-sell across a diversified product portfolio. Recent financial disclosures also show a deliberate portfolio rationalization effort: Upland completed divestitures in 2025 to streamline the business and focus on higher-priority areas. ([investor.uplandsoftware.com](https://investor.uplandsoftware.com/news/news-details/2026/Upland-Software-Reports-First-Quarter-2026-Financial-Results/default.aspx?utm_source=openai)) Geographically, Upland remains a U.S. company headquartered in Austin, Texas, with an international customer base served from that operating platform. Recent highlights include the launch of a new BA Insight platform with integrated AI search features, repeated recognition in G2 market reports, and a July 2025 debt refinancing that replaced existing borrowings with a new $240 million six-year term loan due in 2031, plus a revolving credit facility. Taken together, these developments suggest a company focused on strengthening balance-sheet flexibility while sharpening its positioning around AI-enabled enterprise knowledge management. ([investor.uplandsoftware.com](https://investor.uplandsoftware.com/news/news-details/2026/New-Upland-BA-Insight-Platform-Delivers-Integrated-AI-Search-Experiences-for-Enterprises/default.aspx?utm_source=openai))