#220 - Shay David, CEO of  Retrain.AI - on Product Market Fit resilience

How to create a product that provides a direct line to value for the relevant market. 

This podcast interview focuses on product innovation that has the power to help bring the global unemployment rates down. My guest is Shay David, Co-founder, and CEO of Retrain.AI

Shay David

Shay is a serial entrepreneur who brings many years of experience in dreaming up products and making them a reality: from concept to market, from slideware to hundreds of millions of dollars in sales.

He co-founded Kaltura where he helped define the future of video – thereby taking responsibility as CRO, then GM, and today as a member of the Board. 

Prior to that he co-founded Destinator Technologies, a mobile-GPS-navigation software, and consulted on open systems to Fortune 500 companies

Today he’s the Co-founder, Chairman, and CEO of Retrain.AI a company founded on the vision to make a measurable impact on global unemployment rates by helping 10+ million users find meaningful career opportunities and help enterprises future-proof their organizations. Their mission: To inform, empower and redefine the way enterprises hire, retain and grow their employees. 

And this inspired me, and hence I invited Shay to my podcast. We explore what’s broken in the Talent Development market and why the best strategy for managing HR & talent management today sadly is: “We’ll do tomorrow what we did yesterday.” Shay share’s his vision of how to solve the global talent problem at the core. He also shares his secrets on how to create a sustainable advantage and what needs to be in place to shape a software business that people not only start talking about but keep talking about. 

Here’s one of his quotes: 

Let me ask you, for any organization that you ever worked for when was the last time you logged in to a corporate learning network and expected to actually learn something? The answer is that never happens. Right? 

When was the last time that you get an email from HR that actually had important career advice for you? Again, that never happens. 

When was the last time that a candidate that a company submitted a resume and got a call within 15 minutes saying we’ve processed your request, we think we understand who you are, we have two questions, and we want to schedule an interview for you for tomorrow? Again, that never happens. 

But this is not a joke. This is a problem affecting billions of people every day, the systems that are intended to manage talent acquisition to manage talent organization, and learning and development, those systems are failing. And the cost of that failure is catastrophic. 

During this interview, you will learn four things:

  1. Why having a shared image with your customers about the future state of the world is critical to creating momentum
  2. That a way to understand whether you are on the right track is to ask your customers to articulate in one sentence how you give them immediate value
  3. Why it’s not about finding product-market fit – but keeping product-market fit.
  4. Why, in order to succeed, you shouldn’t think about technology, regulations, or money. That always comes second

For more information about the guest from this week:


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About the author

Sales Pitch

Ton Dobbe is a former B2B software product marketer who's on a mission to save mission-driven SaaS CEOs from the stress of 'not enough' traction. He's the author of The Remarkable Effect, the host of the Tech-Entrepreneur on a Mission podcast, and writes a daily newsletter on the secrets to mastering predictable traction.