The short version.
Rachel Wolan brings over two decades of experience, with a focus on building delightful products for businesses, ranging from SMB to Fortune 500, and applying AI in those product experiences.
Rachel is currently the Chief Product Officer at Webflow, where she oversees Product, Design, Data, UXR, and Pricing & Packaging teams. Webflow has 300k+ customers and powers 15% of the top 5,000 domains.
Her experience spans a diverse range of company stages (Founder, Seed through Series D / pre-IPO, and public), multiple industries (SaaS, Consumer, Martech, Adtech, Service, Sales) and markets (US, EMEA, Asia-Pacific).
Currently focused onEnterprise Agents.Building the trust layer, governance, and composable primitives that let large organizations safely deploy AI agents against real production work.
Previous roles.
- VP & General Manager, Dropbox Core Business. Owned a $2B+ P&L. Ran a 550-person team across Product, Growth, and Engineering. Expanded the business to over 700 million users globally and built the Generative AI product suite, including the Command E acquisition.
- VP Product, LiveRamp. Built products for marketers and launched the CDP business from inception. Built CDP and Data Collaboration platform for several major retailers, QSR chains, and ad platforms. Built major distribution partnership on multiple clouds.
- Head of Product & Design, Talkdesk. First Head of Product (seed round, $30M → $10B), focused on building an enterprise-grade cloud call center, launching the most popular app in the Salesforce ecosystem, and launching the Enterprise AI ecosystem.
- Earlier. Developer and product manager at several startups and enterprises. Helped launch Facebook Ad Network at Facebook in 2008.
Now.
Active mentor at UC Berkeley and angel investor in early-stage SaaS, AI, and design startups. Current portfolio includes Bounti, Metronome, Speakeasy, Prepared, Fermat, Bobyard, CrewAI, GrowthX, You.com, and Ando. Writing on AI products and agentic systems. Maintaining the AI-Native Exec Toolkit.
FAQ.
- Who is Rachel Wolan?
- Chief Product Officer at Webflow, where she oversees Product, Design, Data, UXR, and Pricing & Packaging teams. Over two decades of experience building delightful products for businesses from SMB to Fortune 500, with a focus on applying AI in those product experiences.
- What did Rachel Wolan do before Webflow?
- VP and General Manager of Dropbox’s Core Business ($2B+ P&L, 550-person team, 700M+ users, Generative AI suite incl. Command E acquisition). Before that, VP Product at LiveRamp (launched the CDP business from inception) and Head of Product & Design at Talkdesk (first product hire, seed round to $10B valuation). Earlier: helped launch Facebook Ad Network at Facebook in 2008.
- What is Rachel Wolan’s educational background?
- B.S. from Northwestern University and an M.B.A. from UC Berkeley’s Haas School of Business.
- Does Rachel Wolan invest in startups?
- Yes. Active angel investor in early-stage SaaS, AI, and design startups, and a mentor at UC Berkeley. Current portfolio includes Bounti, Metronome, Speakeasy, Prepared, Fermat, Bobyard, CrewAI, GrowthX, You.com, and Ando.
- How can I contact Rachel Wolan?
- Available for speaking engagements and podcasts. Reach out on LinkedIn or X.