Sales, Leadership & the Power of Connection: Lessons from Kirt Giresi of The Assurance Group
In this episode of the Grit Won’t Quit podcast, host Tom Mirabella sits down with Kirt Giresi of The Assurance Group for an in-depth conversation on sales, leadership, and why meaningful connections are at the heart of business success. With over a decade in the insurance industry, Kirt shares his journey from new agent to team leader, offering valuable insights for anyone looking to excel in sales—or build a high-performing team.
From New Agent to Industry Leader
Kirt began his insurance career in 2013 and joined The Assurance Group in 2018. He’s the first to admit that the industry isn’t easy—there’s no salary safety net, and agents are often selling an intangible product people may not want to think about. But for Kirt, the challenge is worth it.
“People don’t want to talk about dying, and they don’t want to spend money. But when you help them protect their loved ones and save money, the impact is huge,” he says.
From helping clients avoid probate issues to providing financial peace of mind, Kirt sees insurance not as a hard sell, but as a way to create meaningful change in people’s lives.
Why Residual Income and Flexibility Matter
One of the biggest draws to the insurance industry is residual income—the ability to keep earning after the initial sale. Kirt points out that for Medicare plans, many enrollments are $0 to the client, making them an easy conversation starter.
“That residual income gives you flexibility,” he explains. “You can spend more time with your family, pursue what you love, and not be chained to a 9-to-5.”
Leadership That Lifts Others
As a team leader, Kirt believes leadership is about being selfless—giving credit when things go right, taking responsibility when they don’t.
“I love seeing other people succeed,” he says, recalling a time when a new agent with no insurance experience closed a single sale that earned him $40,000 and changed the trajectory of his life.
But leadership also means making tough calls. Not everyone is the right fit for the industry, and part of the job is helping people recognize when another path might make them happier.
Rethinking Prospecting: The TAG Difference
One of the standout differences at The Assurance Group is its lead generation system. Many agents in the industry rely on selling to friends and family or paying for expensive leads—both of which can burn people out quickly.
TAG invests heavily in providing free, high-quality leads to its agents. That means less time chasing prospects and more time building relationships and closing deals. This system is paired with daily training and support to ensure agents make the most of every opportunity.
“When you have a full pipeline, a ‘no’ doesn’t hurt as much. You just move on to the next,” Kirt says. “It helps you avoid what we call ‘commission breath’—that desperation clients can smell a mile away.”
The Power of Suggestion in Sales
Kirt shared one of his favorite sales techniques: the power of suggestion. By asking permission to make a suggestion and starting small—“Let’s just start here and we can add more later”—agents lower the client’s defenses and open the door to bigger opportunities.
“It’s about creating urgency without being pushy,” he explains.
The Game Changer Bonus: Recruiting the Right People
TAG’s Game Changer Bonus offers up to $7,000 for referring someone who becomes a successful agent. But Kirt is quick to point out that success in insurance comes down to just two traits:
Attitude – Staying positive, being grateful, and believing in the opportunity.
Activity – Putting in the time and effort consistently.
“With those two things, you can learn the rest,” he says.
Always Looking for the Right Fit
Kirt’s territory covers the Northeast—New Jersey, Pennsylvania, Maryland, Delaware, Connecticut, Massachusetts, and Rhode Island—and he’s always open to meeting motivated people who want to succeed in insurance sales.
If you’re interested in learning more, Kirt recommends connecting with him on LinkedIn and visiting assurp.com or meetwithtag.com to see an overview of what The Assurance Group offers.
Final Takeaway:
Whether you’re a seasoned sales pro or just starting out, Kirt’s story is a reminder that success comes from building genuine connections, committing to the work, and leading with both purpose and persistence.
This podcast episode was filmed at Wingman Planning in Belmar.
