CELab: The Customer Education Lab

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.

What happens when you stop thinking about “training” and start designing a revenue architecture? In this episode, we down with Sean Reay - a seasoned revenue enablement leader with experience at companies like Outreach and Canva, and now leading enablement for an AI-first CX company, Intercom. We unpack how AI, enablement, customer education, and customer success are converging into one continuous fabric of learning that spans your entire go-to-market motion. This episode dives into ideas like an “operating system for execution that reduces friction,” why many traditional LMS-centric approaches need to evolve (or die), and how AI agents can finally deliver “learning in the flow of work” instead of more information overload. We explore practical patterns - from conversational intelligence tools to AI roleplay and contextual knowledge delivery in Slack - that help revenue and CS teams ramp faster, execute with clarity, and deliver truly personalized experiences at scale. If you’re in Customer Education, Enablement, or Customer Success and trying to make sense of AI, this conversation is a rich, tactical blueprint. Key Takeaways: From training to clarity: Why high-performing teams need an operating system for execution, not just more content. AI in the workflow: How tools like Outreach, Gong, Intercom’s Fin, and AI-powered knowledge systems can surface the right guidance at the exact moment of need. Personalization at scale: Using AI as a layer across your stack to tailor messaging, content, and guidance for different roles, segments, and customer journeys. Agentic learning: The emerging pattern where AI agents watch, listen, and respond across tools (Slack, email, CRM, product) to drive just-in-time learning. Customer education + enablement ≠ silos: How internal enablement content and external customer education should be co-created and re-used, not duplicated in isolation. “Pull” vs. “push” learning: Moving away from mandated content dumps toward on-demand, contextually triggered support in tools like Slack and in-product. AI-assisted coaching: Using call intelligence and AI roleplay to coach sales, CS, and trainers on talk time, questioning, and customer-centric behaviors. Rethinking the LMS: Why static courses and rigid LMS structures struggle in modern SaaS, and what a more dynamic, AI-driven content fabric might look like. Revenue architecture lens: Viewing the entire customer journey—from acquisition through expansion—as a continuous learning and behavior-change system. Accountability and impact sprints: Using impact sprints and clear business outcomes to connect enablement & education work to measurable revenue and retention.

Are you ready to rethink the way your team delivers customer education? In this episode of CELab, host Dave Derington welcomes Sarah Sedgman, CEO and founder of LearnExperts, for an inspiring discussion about the power of AI in instructional design and customer training. Sarah shares her decades of experience transitioning from instructional designer to entrepreneur, and how LearnExperts’ LEAi platform is reshaping training efficiency and scalability for SaaS and enterprise teams. Listen in to discover proven approaches to accelerate course development, create certification-ready exams, and empower both instructional designers and business experts to deliver high-quality, impactful customer learning at scale. Key Topics: How AI in LearnExperts accelerates course creation by up to 85% while ensuring quality and consistency Overcoming human resistance to change when implementing new technology in learning teams Practical use cases: Equipping non-instructional designers to build effective training content Automating exam/question bank creation with built-in best practices for certification Strategies for updating, customizing, and repurposing training materials quickly for evolving business needs The importance of embedding domain expertise and learning science into scalable platforms Enabling customer education teams to address backlogs and prevent customer churn

In the last episode of the CELab podcast, co-host Dave Derington explored the profound shifts redefining the learning landscape—from the legacy of transactional, revenue-generating education services to agile, outcome-driven customer enablement. Customer Education and Education Services are converging, and Dave continues sharing his thoughts on how B2B SaaS organizations are reimagining what learning means for their customers, partners, and teams. Drawing on his journey through small to large businesses - including Atlassian, Outreach, Gainsight, and ServiceRocket - he breaks down why businesses need to move beyond simply selling training—embracing continuous, measurable, and truly impactful learning experiences. This offers listeners an inside look at the systems, teams, and metrics that set elite learning teams apart. Packed with stories from the frontlines—including modular content wins, the challenge of getting measurable outcomes, and real examples of change led by forward-thinking leaders—this episode is a roadmap for anyone looking to level up their Customer Education or Customer Success game. Want to dive deeper or connect with us? Have stories to share? Reach out to us today through this link on the CELab website, or contact us through LinkedIn! Episode Highlights: Transition from revenue-driven to value and outcomes-driven learning strategies. The “Trinity” of learning measurement: Learner identity, what’s learned, and usage data. Modular, scalable content as a key to modern learning success. Importance of aligning education, enablement, services, and customer success teams. Continuous learning loops beat one-and-done training every time. Tailoring without fully bespoke (costly) solutions: Balancing scale and relevance. Embedding data and business outcomes in learning program design. Practical examples from Atlassian, Gainsight, and more. Tips for leveraging champions and blended content delivery.

What does the future hold for Customer Education in the ever-evolving world of B2B SaaS? In this solo episode, CELab co-founder and host Dave Derington explores the profound shifts redefining the learning landscape—from the legacy of transactional, revenue-generating education services to agile, outcome-driven customer enablement. Drawing on industry experience and personal insights, Dave examines how the disciplines of Education Services and Customer Education are merging to drive both business outcomes and Customer Success. Listeners will discover how digital transformation, the subscription economy, and post-pandemic realities have forced learning organizations to adapt at unprecedented speed. Using real-world examples and honest reflection, Dave highlights practical strategies, common pitfalls, and the importance of continual innovation in customer education. Whether you lead a startup or enterprise, this episode arms you with actionable ideas for thriving in the modern era of learning. Key Highlights: Why Education Services and Customer Education are converging in SaaS Lessons from legacy revenue-driven versus outcomes-based models How the subscription economy demands faster, more agile learning solutions COVID-19’s lasting impact on digital learning and engagement Key risks in “old school” and modern on-demand training programs The real-world business value of blending live and digital learning Practical steps to improve adoption, reduce churn, and drive measurable customer success The critical role of customer success-minded educators in today’s SaaS world