In this end-of-year special, Adam Avramescu and Dave Derington look back at 2025 through the lens of the things they love most outside of work: video games and live music. They unpack how titles like Helldivers 2, Peak, and Megabonk model great onboarding, community-based learning, and continuous engagement—and what Customer Education and Customer Success teams can steal from modern game design.
On the music side, they explore Louis Cole, King Gizzard & the Lizard Wizard, Black Country, New Road, St. Vincent, and Tune-Yards. Adam and Dave connect venue, context, and stagecraft to how we design learning environments, build resilient teams, and foster community around our programs. If you’re thinking about onboarding, product adoption, AI-era education, or how to keep your learners coming back, this episode is packed with fresh, unexpected parallels.
Onboarding by design: How Helldivers 2 uses scaffolding, mission flow, and “muscle memory over menus” to teach complex mechanics—mirroring ideal SaaS onboarding.
Context > content: Why the venue (Small venue vs. big noisy hall) transformed Louis Cole vs. King Gizzard orchestral shows—and how that maps to learning environments and attention.
Performance support vs. upfront training: Games as a model for balancing early instruction with in-the-moment guidance.
Community-based learning:Peakas a metaphor for learners pulling each other up the mountain via collaboration and shared discovery.
Resilient teams after setbacks: Black Country, New Road rebuilding after losing their lead singer—parallels to CE teams navigating layoffs and org changes.
Emergent learning & retention: How Megabonk and other games keep players experimenting and returning, similar to driving ongoing product adoption.
Edges and surprise in learning:St. Vincent and Tune-Yards using surprise, constraints, and audience participation to create memorable experiences—vs. bland, predictable training.
AI and emergent workflows: Early thoughts on how AI products shift education from “where to click” to “how to think and prompt.”
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
In this episode of the Customer Education Lab, host Dave Derington welcomes Dan Braithwaite, Senior Director of Product Training at Mediaocean, for a deep dive on modern Instructor-Led Training (ILT) and its powerful impact in B2B SaaS customer education. Dan shares real-world stories, practical frameworks, and a human-centered approach to ILT that has helped shape Mediaocean’s global learning strategy.
Tune in as we debunk ILT myths, unpack a hands-on framework spanning “Tell Me, Show Me, Let Me Try,” and discuss how to build truly engaging experiences for customers and internal learners. If you want actionable strategies on scaling customer education, maximizing engagement, and measuring impact, this episode is a must-listen!
Key Episode Topics & Highlights
ILT’s evolution: from “dead” to indispensable in SaaS training
Building global, scalable, virtual instructor-led programs
“Tell Me, Show Me, Let Me Try” framework
Multimodal learning and accommodating diverse learner styles
Turning classrooms into communities & leveraging peer learning
Avoiding common mistakes in new ILT programs
The power of thoughtful post-training experiences and measurement
Using feedback loops, NPS, support ticket data, and product engagement tools
Driving adoption, retention, and tangible business impact via training
In this episode of CELab, host Dave Derington sits down with April Trask, a leader in partner enablement and enterprise AI at Writer. April unpacks the evolving landscape of partner enablement, exploring how AI and generative tools are reshaping the way organizations educate both partners and customers. April shares her unique journey from academia to tech, offering candid insights into building scalable programs at companies like Dropbox, Slack, CrowdStrike, and Writer. The conversation dives deep into the differences between customer education and partner enablement, the challenges of aligning cross-functional teams, and the importance of adaptability in a rapidly changing industry. April and Dave also discuss practical strategies for leveraging AI in learning, the critical role of collaboration with product and marketing, and advice for professionals navigating the pressures of pipeline and revenue.
Key Topics & Takeaways for Customer Education and Customer Success:
The spectrum of partner enablement models and why “one size fits all” doesn’t work
How AI and generative tools are transforming learning experiences for partners and customers
The difference in motivations between partners and direct customers—and why it matters
Building scalable enablement programs from scratch in fast-growing companies
The importance of cross-functional collaboration (product, marketing, sales enablement)
Why playbooks must be flexible: lessons learned from adapting to new environments
Career advice for those moving from customer education to partner enablement
Launching a customer education program is never easy—especially when you’re racing against the clock. In this episode, CELab’s Dave Derington sits down with Clea Mahoney , Head of Customer Education at Rewst, to unpack how her team rolled out Skilljar’s LMS in just 55 days. Clea shares her unconventional journey from instructor-led training to scalable online learning, and how playfulness, experimentation, and a customer-first mindset fueled Rewst’s rapid growth.
Listeners will discover how Clea and her team navigated the challenges of startup life, balanced perfectionism with progress, and leveraged data and AI to drive customer success. Whether you’re building your first customer education program or scaling an established one, this episode is packed with actionable insights, candid stories, and inspiration for every stage of your journey.
Key Topics & Highlights:
Rapid implementation of Skilljar LMS in just 55 days
Transitioning from instructor-led to scalable, modular online training
Building customer education programs in fast-paced startup environments
Balancing perfectionism with progress: “done is better than perfect”
Using data and analytics to measure and improve learning outcomes
Integrating AI and contextual help into customer education platforms
The importance of soft skills and team culture in Customer Success
Tailoring education for technical and non-technical audiences
Advice for launching your first customer education program
In this episode of CELab, we welcome Nick Mehta and Erica Kuhl to talk about Skilljar by Gainsight! We discuss the integration of their platforms and the future of Customer Education. We explore the importance of community in customer success, the vision behind the Customer OS, and how learning and community can work together to enhance customer experiences. Erica shares her journey from Salesforce to Gainsight, emphasizing the need for collaboration and innovation in the customer education space. The conversation highlights the significance of integrating learning and community to drive customer success and retention.
Highlights
Customer education is essential for growth and retention.
The integration of SkillJar and Gainsight creates a powerful Customer OS.
Community plays a crucial role in customer success.
Learning should be an ecosystem that includes community engagement.
Erica Kuhl emphasizes the importance of collaboration in education.
The future of customer education lies in integrating various platforms.
AI can enhance the customer education experience.
Creating opportunities for practitioners to connect is vital.
Feedback from the community is essential for product development.
The vision for Gainsight is to empower customers through education and community.
