Who We Are — Thrive Benefits Group
Who We Are

A Family Firm With a Head for Numbers

Thrive Benefits Group is a licensed employee benefits advisory built by a family and run like one — the numbers do the talking, and the people behind them answer the phone.

Our Story

Built on Service, Proven With Numbers

Brian Little spent three decades building businesses and fifteen years inside the insurance industry. What he kept seeing was the same gap: employers paying more every year for benefits, and employees using them less. Thrive Benefits Group was his answer — a firm built on the belief that serving people well and running the numbers honestly aren't competing priorities. They're the same job.

What started with Brian grew into a family operation in the most literal sense — two generations of Littles work here, alongside advisors who've been welcomed in like family. That's not a branding angle. It's why clients get callbacks on the first ring and straight answers on the first call.

We show employers money they didn't know they had — then prove it, payroll by payroll.

Today TBG designs benefit programs — SIMRP, DPC-anchored plans, supplementals, group health — for nonprofits, care organizations, and employers who need every dollar to work. No new budget required. The results are on our case study pages, with real names attached.

The Core Team

The People Behind the Math

Brian Little

Brian Little

CEO · Co-Founder

Thirty years an entrepreneur, fifteen in insurance. A man of humble beginnings with an enormous heart for people — his willingness to serve others is the cornerstone TBG was built on.

Jordan Little

Jordan Little

COO · Co-Founder

Behind the scenes for all things TBG. Jordan has helped launch and grow organizations across three industries — if you have a big vision, he's the one who takes it to fruition.

Sydney Little

Sydney Little

Director of Operations

The glue that holds it all together. Degrees in Public Relations and Business, seven-plus years in executive administration, and attention to detail that's simply unmatched.

Jacob Guidi

Jacob Guidi

Sales Account Executive

A top insurance producer painstakingly devoted to protecting his clients — if there's a solution to your need, Jacob will find it. Currently finishing his doctorate.

Jeremy Little

Jeremy Little

Director of Relationship Development

Our jolly giant — 6'7" with an incredible way of making people feel seen and heard. Clients and staff alike love him for his infectiously joyous attitude.

Put Us to Work

See What the Numbers Say for Your Organization

We'll pull a custom savings breakdown based on your headcount — free, specific, and yours to keep either way.