CELab - Ep 172 - Bessie Weiss - From PLG Darling to Enterprise Powerhouse: How Webflow Scales Customer Education

In this episode of CELab – The Customer Education Lab, host Adam Avramescu sits down with Bessie Weiss, Senior Director of Customer Education at Webflow, to unpack what it really takes to evolve a beloved PLG education motion into an enterprise-ready engine. Bessie shares how she inherited the iconic Webflow University, the “don’t mess it up” mandate from leadership, and the practical tradeoffs her team makes every day between pixel-perfect production and keeping pace with a rapidly changing SaaS + AI product. They dive into the org design behind Webflow’s modern education function—video production, instructional design, platform, certifications, and onboarding—and how those pieces work together to support both self-serve users and large enterprise accounts. From launching high-stakes certifications in under a year, to deciding when humor helps (or hurts) learning, to using AI for exam development and just‑in‑time learning, this episode is a masterclass for Customer Education and Customer Success leaders building programs that actually move product adoption and revenue. Highlights: How Webflow University evolved from PLG top-of-funnel magnet to a dual PLG + enterprise education engine. The “make it better, but don’t mess it up” mandate when inheriting a beloved program and community. Balancing high production value vs. speed and scalability in a fast-changing SaaS + AI product. Where marketing ends and education begins—and how Webflow split teams and responsibilities. Structuring a modern education org: video, instructional design, platform/experience, certifications, onboarding. Why rigid instructional design can backfire—and how to flex based on audience (developers vs. designers vs. marketers). Designing high‑stakes, AI‑proctored certifications that are meaningful to partners and the ecosystem. Using AI as a tool for question authoring, psychometrics, and in‑product just‑in‑time learning—without replacing humans. Metrics that matter in PLG vs. enterprise: traffic and conversion vs. time‑to‑value, renewal, and expansion. The future: customers learning via agents and contextual AI, but still needing conceptual scaffolding and strategy.

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