Jessy Cross

Born and raised in Polk City, Florida, Jessy Cross brings a hometown mindset and strong work ethic to his role as a licensed insurance agent with HealthMarkets Insurance Agency. His local roots shape the way he works with clients — focused on trust, consistency, and doing right by the people he serves.

Jessy helps individuals, families, and retirees navigate health insurance and Medicare options, including Medicare Advantage, Medicare Supplement, dental, vision, and supplemental plans. By working with multiple insurance carriers, he’s able to offer unbiased comparisons and help clients choose coverage that fits their real-world needs — not just what looks good on paper.

Rather than rushing decisions, Jessy emphasizes education and simplicity. He believes clients should feel confident and informed, not overwhelmed, when choosing insurance. From first-time health coverage to Medicare enrollment and annual plan reviews, he stays involved long after the policy is in place.

Known for being approachable, responsive, and detail-oriented, Jessy takes pride in making insurance easier to understand and easier to manage — always at no cost to the client.