Selling What They Think Is Free with Eric Appel

Selling What They Think Is Free with Eric Appel

From Make It Happen Mondays - B2B Sales Talk with John Barrows by John Barrows

April 13, 2026 · 58 min · Episode 465

About this episode

John Barrows interviews Eric Appel about positioning and selling in a market where prospects believe they can get products for free.

If your prospect thinks they can already get what you're selling for free, you don't have a product problem — you have a positioning problem. In this episode, John sits down with Eric Appel, CRO of Island, the company that turned a free commodity — the browser — into one of the fastest-growing enterprise security platforms in the world. Eric pulls back the curtain on how Island landed eight of the top ten US financial institutions as early customers, why the advisor network beats outbound at scale, and what today's sales reps are getting catastrophically wrong before they even open their mouths. If you're navigating a market where AI is commoditizing everything around you and buyers think they don't need what you're selling, this conversation will change how you think about value, positioning, and the future of selling. Visit www.jbarrows.com and learn how you can Make It Happen. What You’ll Learn How Island sold a "free" product to the world's biggest enterprises — and won The advisor network strategy that replaced traditional outbound prospecting Why the first 15 sales hires at Island were all known killers — and why that matters How to build a real feedback loop between sales…

People in this episode

Host: John Barrows

Guest: Eric Appel

Topics covered

  • sales positioning
  • enterprise security
  • AI in sales
  • prospecting strategies
  • value selling

Keywords

  • sales
  • positioning
  • enterprise
  • prospecting
  • AI
  • value
  • feedback loop

Mentioned in this episode

Organizations: Island, US financial institutions, AI

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