“How do we drive real skills transformation within a company?”

That’s the question we explore in this episode with Eran Vaisfailr, former Product Owner of Learning and Development at Booking.com, now Co-founder and CEO of Plynn, a learning startup focused on turning informal learning into measurable skills. In his time at Booking.com, Eran was at the forefront of building a skills-based organisation, focusing on aligning employee capabilities with business needs.

Our conversation explores why skills-based transformation isn't just about formal training systems or shiny new AI tools. Eran shares his experience at Booking.com, where skills intelligence was key. He highlights how day-to-day work, projects, and even platforms like YouTube often offer more valuable learning insights than LMS completion rates.

If you’re feeling the pressure of complex skills frameworks and a widening gap between training and performance, this episode offers a grounded roadmap for L&D’s evolution in the age of AI.

Some curious takeaways:

• Skills transformations fail when data foundations aren’t clean and aligned
• Measuring performance improvement is the true test of a skills programme’s success
• Start skills work where the business feels the pain, not everywhere at once

Episode highlights:

(00:00) Welcome to Harald’s Curious Corner

(04:26) The biggest mistakes organisations make when implementing LMSs

(10:12) Consolidating learning data in complex organisations

(12:45) Why Booking.com invested in a skills-based organisation

(15:06) Skills only matter when you can prove them

(20:04) The hidden data challenges behind skills verification

(23:36) Working with business leaders on skills change

(28:33) The real reason skills data never lines up

(32:32) Why one-size-fits-all learning keeps failing

(37:37) Turning YouTube into structured, trackable learning

(42:56) Why L&D can’t own just-in-time learning alone

(50:03) Reducing system overload and designing learning where work happens

(52:21) Curious Corner Takeaways

Connect with the guests:

Eran Vaisfailr on LinkedIn: https://www.linkedin.com/in/eran-vaisfailr/ 

Explore Plynn: https://www.plynn.dev/ 

Follow me on the following sites:

Harald Overaa on LinkedIn: https://www.linkedin.com/in/haraldovera/ 

Subscribe to Harald’s Newsletter: https://www.linkedin.com/newsletters/6901795950403186688/