Ep. 75 - Preparing for the war of founding a SaaS with Guy Benjamin, CEO and co-founder of Healthee

Does anyone really understand their health benefits? 

Most of us have experienced going to HR with a benefits question, only to be redirected to a call center just to sit on hold and maybe get answers.

Guy Benjamin, CEO and co-founder of Healthee, developed a way to simplify this age-old problem with a platform that lets employees easily navigate their health and wellness benefits, and even helps choose the best plan for them.

In just two years, Healthee has managed to raise $26 million dollars. But it hasn’t been simple or easy. Benjamin declares that starting Healthee has been his toughest challenge yet - even more challenging his prior experience as an Israeli fighter pilot. 

He shares his experience as a founder, and other key takeaways including:

• The perks of outsourcing the R&D team from Israel (and spoiler, they are not all financial)
• How AI boosts customer experience and gives key insights to employers
• Hiring the right experts to fill in your knowledge gaps
• Finding the champion in the organization you’re selling to - in this case it’s HR

Other resources to check out:

Interview with Vinay Bhagat, Founder and CEO of TrustRadius who publish a yearly report about how B2B buyer behavior is changing.

The Lead Gen Mistake I Guarantee You’re Making – how to create content that better identifies intent from today’s b2b buyer.

And, if you want an outside look at your content with actionable advice, take advantage of our Content Audit. Valued at $20K in free consulting.

---

Not Getting Enough Demos?

Your messaging could be turning buyers away before you even get a chance to pitch.

🔗 Get a Free Messaging & Conversion Review

We’ll analyze your website and content through the eyes of your buyers to uncover what’s stopping them from booking a demo. Then, we’ll give you a personalized report with practical recommendations to help you turn more visitors into sales conversations.

And the best part?

💡 It’s completely free.

No commitments, no pressure—just actionable advice to help you book more demos.

Your next demo is just a click away—claim your free review now.