Blackbird.AI Chief Revenue Officer Anna Osborn is one of The Top Women Leaders in Software of 2025
The Software Report is pleased to announce the Top Women Leaders in Software of 2025. These women are leading key functions inside some of the most widely used, fast-growing, and technically complex software organizations. Their work spans product, engineering, revenue, marketing, and operations—often in roles where decisions directly shape company direction and customer outcomes.
Anna Osborn is the Chief Revenue Officer of Blackbird.AI, where she is in charge of global revenue strategy and scales the commercial organization behind the company’s Narrative Intelligence Platform. Anna focuses on building high-performing teams, sharpening go-to-market execution, and helping enterprises adopt technology that protects them from narrative-based disinformation campaigns.
In 2025, the company’s commercial growth accelerated. Blackbird.AI reported 118% year-over-year ARR growth, tripled customer wins, and secured strategic funding, bringing total capital raised to $58 million. As CRO, Anna plays a central role in translating this demand into durable customer relationships and sustainable growth.
Before joining Blackbird.AI, Anna served as CRO at Exiger, where she led the company’s transformation into a supply chain SaaS platform, contributing to its $1.2 billion acquisition by Carlyle Group and Insight Partners. Earlier in her career, she held senior roles at Thomson Reuters and Kroll. Anna holds a bachelor’s degree in marketing from Michigan State University and is a strong advocate for diversity and healthy organizational culture.