Anna Baird spent years as a CFO, COO, president, and CRO—including helping Outreach grow from about $25M to over $1B in value—and before that spent 17 years at KPMG, where she was the lead partner for Google before its IPO and later worked with McAfee's leadership on board and acquisition matters. At Madrona, she focuses on the practical side of scaling a company, like building customer proof before a product launch, understanding why buyers hesitate to adopt new tools, and using founders' public visibility to build trust, while also serving on the boards of Semrush and SeatGeek, where she chairs the audit committee.