Upland Software announced that former executive Sean Nathaniel will become its chief executive officer, effective May 1 2026. Nathaniel previously served as Upland’s chief technology officer and executive vice president of workflow automation solutions before leading DryvIQ, an AI‑driven unstructured data management company, as president and CEO for four years.
The appointment comes as Upland accelerates its shift toward AI‑powered knowledge and content management. The company has already begun divesting lower‑margin assets and has seen its adjusted EBITDA margin rise from 20% in Q2 2024 to 25% in Q2 2025, with guidance that the margin will exceed 30% in Q3 2025. Core organic growth, which was flat in Q1 2025, is projected to be 2% in Q2 2025 and over 4% in 2026, reflecting the growing demand for subscription‑based, high‑margin products.
Nathaniel said, “Enterprises are sitting on a massive amount of knowledge, content, and data, but until it’s contextualized, governed, and trusted, it can’t effectively power AI. That’s exactly what Upland solves. As CEO, my priority will be to ensure Upland serves as a core intelligence layer for the agentic enterprise, enabling customers to unlock the full value of their knowledge, content, and data as they scale AI and agent‑driven operating models.” Chairman Jack McDonald added that the company has “beaten our revenue and adjusted EBITDA guidance midpoints” and that the AI product portfolio is gaining traction with new multi‑year customer wins.
Investors remain cautious because recent revenue declines have weighed on sentiment, even as margin expansion and a clearer AI strategy provide a more favorable outlook. The company’s focus on high‑margin, subscription‑based solutions and its debt refinancing efforts are intended to strengthen its balance sheet and support continued growth.
The CEO transition signals continuity in leadership while reinforcing Upland’s commitment to AI and higher‑margin operations. With Nathaniel’s deep experience in both Upland’s technology stack and AI‑centric business models, the company is positioned to accelerate its transformation and pursue new growth opportunities in regulated industries.
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