Sam Newland, CFP®
A fiduciary path, sixteen years in the making
The path started in 2009. Sam's father was diagnosed with cancer, and the experience pulled him into the intersection of healthcare and personal finance. How a family pays for care, what coverage actually does, where the system breaks down, and what it costs the people inside it.
In 2013 Sam joined HealthMarkets, then a subsidiary of Blackstone. That's where the industry education began. Over the next several years, the work shifted away from individual policies and toward employer-side benefits, where the complexity is higher and the impact spans dozens or hundreds of lives at a time.
Sam left HealthMarkets because pitching a single set of solutions to every client is not a fiduciary act. The right answer for a company depends on its size, its workforce, its claims history, its tolerance for risk, and the funding arrangement that actually fits — not the one the agent happens to sell. To do that work properly meant building a brokerage with no captive ties.
At 26, Sam earned the Certified Financial Planner designation — and earned it in four months, from first textbook to passing the board exam, against the two- to three-year arc most candidates take. The pursuit wasn't required by the role. It was a deliberate move to deepen the analytical toolkit he could bring to every client recommendation. The CFP curriculum forces a discipline most benefits brokers never touch: tax, investments, retirement, insurance, and estate planning, all read together. The same focus that compressed three years of study into four months — full domains absorbed quickly, then applied — is still the operating speed at Benefitra: read everything, ask the harder questions, finish faster.
In 2018, the PEO question arrived. A client asked Sam about PEOs and he didn't know the answer. He asked a longtime industry colleague, who shrugged and said, "they're the competition." That answer pointed at a much bigger map. Sam started reading the white papers, learning the math behind level-funded plans, captives, reference-based pricing, MEWAs, and the rest of the alternative-funding landscape that most brokerages either don't sell or don't understand.
Benefitra is the extension of that work. A brokerage operating across all seven funding arrangements, instead of the one or two most agents are equipped to discuss. A SaaS platform that elegantly organizes policies and employee information, makes benefits administration easier for both the agent and the client, and delivers significant time and financial savings versus standard industry competitors. And a small, focused team that values curiosity, math, and doing the right thing for the client over selling whatever the carrier discounts hardest this quarter.
Pragmatic, driven by constant improvement, constantly curious, and built to help businesses save, succeed, and grow.
Win deals. Win talent. Win on costs.
Three outcomes every employer is trying to land at once. Benefitra is structured around all three, not just one.
Better benefits per dollar
We design the plan around what the workforce will actually use, then we shop the funding arrangement that delivers that plan at the lowest defensible cost. The math is the proof.
Stronger teams
Benefits people understand are benefits people use. We build the materials, the open-enrollment flow, and the year-round support that turn a binder into a tool the workforce values.
Win more deals
For brokers and agents on our platform: the same tools, calculators, and materials we use to close our own book. Modern automation that lets one operator do the work of many.
A brokerage, a platform, and a marketing arm — under one roof
Three lines of work that compound on each other. The brokerage funds the platform. The platform multiplies the brokerage. The marketing arm scales the agents who use both.
Employee Benefits Brokerage
Independent. Not captive. Expert across all seven funding arrangements: fully insured, level-funded, self-funded, self-funded captives, ICHRA, PEO-integrated, and Taft-Hartley. We design the right fit, not the easy one.
Marketing Arm
Websites, SEO, social content, and inbound-lead systems built for the trades. Currently focused on roofing and adjacent construction verticals, run by a dedicated team that knows that buyer and that sales cycle.
"Our superpower is making one operator as productive as twenty-six full-time employees."
Through automated marketing, SEO, and the technology layer we have built ourselves — leagues ahead of what most operators using "AI" are actually doing. The same leverage we apply to our own book is what we ship to the brokers and agents on our platform.
Small, sharp, distributed
Eight operators across benefits, technology, and growth. Every role is hands-on.
Sam Newland, CFP®
Juan Reyes
Vin Cannistraro
Scott Breault
Noa Belillti
Salveena Khan
Shalom Tellis
Harrison Piper
Independent
Not captive. Not tied to a specific carrier or solution set. Every recommendation comes from the math, not the contract.
Fiduciary by design
Sam earned the CFP® designation at 26 to formalize what was already the operating standard: act in the client's best interest, full stop.
Curiosity as a discipline
The funding landscape changes every renewal. We read the white papers, run the analysis, and bring back the option that fits — not the one we already know how to sell.
Ready to see what your benefits could be?
Bring your current plan, your renewal, and your headcount. We will show you the math across every funding arrangement that could work — and you decide what fits.