BIORachel Wolan / CPO, Webflow

Bio.

Building product orgs that ship with AI in the loop, not around it.

The builder.

Two decades shipping delightful, enduring, applied AI products. The last several years spent rewiring product orgs to run with both AI and humans in the loop.

Currently Chief Product Officer at Webflow, leading Product, Design, Data, UXR, and Pricing & Packaging across 300k+ customers and 15% of the top 5,000 domains. Led the transition from PLG no-code website builder to SLG agentic marketing platform, with thousands of enterprise customers running agents daily in production.

Range: founder; seed through Series D, pre-IPO, and public. SaaS, consumer, martech, adtech, healthtech, edtech, servicetech, salestech. 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.

Operating style.

Sees her job as building a product factory: distributed product judgment, faster cross-functional decisions, quality as the bar. Still ships and codes daily, builds in public. Doesn’t need a big org to figure out what to build. Hires very senior, high-agency IC builders; keeps the structure flat; runs a low-meeting, low-process, low-ego culture with room to explore. Takes product risks, doubles down on winners, kills losers.

What she’s building.

Inside Webflow, the focus above. Outside Webflow, an open set of artifacts on how operators and orgs actually go agent-first:

  • Becoming Agentic. A working series on what shifts when an individual operator, and then a whole org, rebuilds around agents.
  • The Toolkit. Open library of prompts, patterns, prototyping personas, and operating playbooks for executives building with AI.
  • The Builder Factory and AI-Native Org. Opinionated views on what a product org should look like in 2026.
  • Prototyping Personas. The pattern library underneath how most of this work ships.

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.
  • CEO & Co-founder, YadaZing. Built an English-learning product on top of YouTube videos using transcription, NLP, and human-in-the-loop work (pre-LLM era), sold it directly into schools, and raised a round.
  • Earlier. Developer and product manager at several startups and enterprises. Helped launch Facebook Ad Network at Facebook in 2008.

Investing & teaching.

Active angel investor in early-stage SaaS, AI, and design startups; mentor at UC Berkeley. Portfolio includes Ando, Bobyard, Bounti, CrewAI, Fermat, GrowthX, Metronome (exited), Prepared (exited), Speakeasy, Starfolk, and You.com.

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. Portfolio includes Ando, Bobyard, Bounti, CrewAI, Fermat, GrowthX, Metronome (exited), Prepared (exited), Speakeasy, Starfolk, and You.com.
What is Rachel Wolan currently focused on?
Enterprise Agents: building the trust layer, governance, and composable primitives that let large organizations safely deploy AI agents against real production work.
Where can I read Rachel Wolan’s writing on AI?
The Becoming Agentic series covers what shifts when operators and orgs go agent-first. The Toolkit is an open library of prompts, patterns, and operating playbooks for executives building with AI.
How can I contact Rachel Wolan?
Available for speaking engagements and podcasts. Reach out on LinkedIn or X.