Jack DeBrabander Is Building a Compliance-First Toolkit for Insurance Sales Teams

The health insurance sales business is undergoing a change. Federal regulators received roughly 275,000 complaints in 2025 from consumers who said they were enrolled in Marketplace coverage or switched to a new plan without their consent. In September, the Centers for Medicare & Medicaid Services froze new agent and broker registrations ahead of the 2027 open enrollment period and ordered existing agents to re-verify their identities.

Jack DeBrabander saw the problem coming from the inside. A licensed health insurance agent who works through Compass Health Consultants, DeBrabander spent his early years in the business watching agencies chase volume with tools that were not intended for a regulated industry. So he built his own.

Today he runs three connected businesses under the Strategy name: StrategyB, a CRM platform for sales teams; Strategy Data Solutions, a phone list compliance service; and Strategy Health, a licensed agency that helps self-employed workers and families find private health coverage.

“Most of the trouble in this industry comes from shortcuts,” DeBrabander says. “Calling people who never asked to be called. Texting from lists nobody checked. Enrolling people who never really said yes. I wanted to build tools that make the right way the easy way.”

From engineering to entrepreneurship

DeBrabander’s path into business software started far from insurance. He earned a degree from Michigan State University’s School of Packaging and spent two years as a controls systems engineering intern at Central Process Engineering, building and implementing control system changes alongside engineers and technicians.

“Engineering teaches you to look at the whole system and find the weak point,” he says. “In insurance sales, the weak point is almost always the data and the process around it. If those are broken, nothing downstream works.”

Building the stack

StrategyB is designed to be an all-in-one customer relationship management system (CRM) for agents and sales teams. It’s meant to combine SMS (text) and voice messaging, automated follow-up workflows, appointment booking through third-party calendar sites, and team performance dashboards in a single platform. DeBrabander says he built it with 10DLC-compliant messaging out of the box, a carrier registration standard for businesses that send text messages at scale.

Strategy Data Solutions, which operates at dncready.com, is meant to address the problem one step earlier. Sales teams can upload a phone list, and every number should come back tagged as mobile or landline, is checked against the National Do Not Call Registry, and flagged if it belongs to a known serial litigator under the Telephone Consumer Protection Act. Clean rows can be pushed directly into a StrategyB workflow.

DeBrabander says the service runs on a prepaid, per-number model with no contracts or monthly fees, and duplicate or invalid numbers are never charged.

“TCPA lawsuits can cost an agency $500 to $1,500 per call or text,” DeBrabander says. “One bad list can sink a small business. Scrubbing it first costs a fraction of that, and it means you’re only reaching people who actually want to hear from you.”

Coverage for people the system leaves out

On the consumer side, Strategy Health was created to focus on a group DeBrabander says is increasingly underserved: the self-employed, small-business owners, early retirees, and families who earn too much to qualify for Marketplace subsidies.

That group grew this year. The enhanced premium tax credits that lowered costs for millions of Americans expired at the end of 2025, and subsidies are again limited to households earning between 100% and 400% of the federal poverty level. A family that earns even slightly above that line now typically pays full price.

Strategy Health compares private-market PPO plans from major national carriers alongside Marketplace options and lets the client choose. Because private plans are medically underwritten, pricing and eligibility depend on health history, so the agency quotes both.

“Nobody should leave without coverage,” DeBrabander says. “If a private plan is the better deal, great. If someone needs the Marketplace because of a pre-existing condition or because they qualify for help, we enroll them there. The point is to show people every option honestly and let them decide.”

What other founders can learn

DeBrabander says the regulatory pressure on his industry carries a broader lesson for entrepreneurs in any space where public trust is fragile.

“A lot of founders treat compliance as a cost,” he says. “I treat it as the product. When regulators raise the bar, the companies that were already clearing it get stronger. The ones cutting corners don’t survive.”

He expects the tighter federal rules to shrink the field of agents and push consumers toward advisors with clean track records. For the tools he builds, that shift is the market.

“The bad actors make it harder for everyone, so I’m glad to see the standards go up,” he says. “Be honest with people, respect their time, and make sure they understand what they’re agreeing to. Build your business on that, and it takes care of itself.”

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