Selling What They Think Is Free with Eric Appel

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 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 and engineering The three questions you should never ask a prospect (and what to do instead) Why hypothesis selling is replacing discovery in today's AI-driven sales environment What separates leaders from followers in the AI era — and why followers will get left behind Eric Appel is the Chief Revenue Officer at Island, the enterprise browser company redefining how organizations think about security, productivity, and AI enablement. With a career that spans Arthur Anderson, Yahoo, McAfee, and some of the most pivotal chapters in information security, Eric has spent over two decades building go-to-market engines for category-defining companies. At Island, he helped architect the sales strategy that brought the world's largest financial institutions, pharma companies, and global enterprises onto the platform — proving that even a "free" product can command a premium price when the value proposition is airtight. Connect with Eric Appel: Website: LinkedIn: John Barrows is a sales trainer, speaker, and founder of JB Sales with over 25 years of experience in the industry. He has made hundreds of cold calls a week, led startups to acquisition, and trained high-performing teams at companies like Salesforce, LinkedIn, Amazon, and Okta. Through JB Sales, John focuses on practical sales execution—helping reps fill pipeline, close deals, and build trust with buyers in today’s AI-driven sales environment. Connect with John Barrows: LinkedIn: Instagram: TikTok: Check out John's Membership: Join John's Newsletter:

You can listen to Selling What They Think Is Free with Eric Appel online on Radio and Podcast. Open the player on this page to stream the available audio.

Selling What They Think Is Free with Eric Appel is an episode from Make It Happen Mondays - B2B Sales Talk with John Barrows by John Barrows.

This episode is 57:52 long.

This episode was published on Apr 13, 2026.

Yes. Use the heart button on the episode page to add it to your favorite episodes list.

Yes. This page shows related episodes from Make It Happen Mondays - B2B Sales Talk with John Barrows when more episodes are available from the podcast feed.