#092 The Referral Engine: Jay Wolfberg on Building a Business That Grows Through Trust

Built For This Podcast, with Carly Pepin

October 22, 2026 by

Carly Pepin

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In this episode of Built For This, Carly Pepin sits down with Jay Wolfberg, President of We Insure, to explore how relationships, consistency, and customer-focused leadership can turn a small business into a thriving organization.

Jay shares his unconventional journey from managing Radio Shack stores and navigating the real estate industry to building one of We Insure's most successful franchises, generating more than $32 million in annual premiums before eventually becoming president of the company.

Carly and Jay explore how he built a powerful referral-driven business through what he calls "hyper-responsiveness" and "relentless consistency." They also discuss the challenges of moving from franchise owner to corporate leader, rebuilding trust after an acquisition, and creating a culture built around his belief that happy people sell more.

They also examine the importance of in-person collaboration, peer-to-peer learning, and how AI can help employees work more efficiently without replacing the human relationships that drive business success.

Key Takeaways

Build Relationships That Turn Customers Into Advocates

Jay believes referrals are one of the most valuable ways to grow a business. By responding quickly, delivering consistently excellent service, and actively asking satisfied customers for referrals, he built a business that attracted new clients without relying heavily on traditional marketing.

Great Leadership Starts With Helping Others Succeed

After becoming president of We Insure, Jay focused on rebuilding relationships, removing unnecessary obstacles, and giving franchisees the support they needed to succeed. His philosophy is simple: happy people sell more. When leaders create an environment where people feel supported and empowered, stronger business results follow.

Technology Should Empower People, Not Replace Them

Jay sees AI as an opportunity to simplify administrative tasks, make complex insurance information easier to understand, and free employees to focus on customers. For him, the goal isn't replacing insurance agents but giving them better tools to deliver a more personal and valuable experience.

About Jay Wolfberg

Jay Wolfberg is the President of We Insure, one of the nation's fastest-growing insurance franchise networks, where he focuses on helping franchise owners build successful, sustainable businesses.

Jay's career has taken him from retail management and real estate into insurance entrepreneurship. Following the 2008 financial crisis, he became a We Insure franchise owner in South Florida, eventually growing his agency into a multi-location operation generating more than $32 million in annual premiums.

Today, Jay draws on his firsthand experience as a franchisee to strengthen relationships, support entrepreneurs, and create opportunities for others to achieve financial freedom through business ownership.

Memorable Quotes
"The most valuable way to acquire a customer is through a referral."
"Happy people sell more."
"We want the AI to augment the agent, not replace the agent."

Jay Wolfberg