Ingram's July 2026

NUMBER ONE

Brandy Thompson, CEO of benefitbay.

benefitbay

Growth: 873.78% 2022: $872,215

Average Annual Growth Rate: 291.26%

1 st Year

Gross Revenue: 2025: $8,493,494 Full-time employees: 100 Four years before its trek to be the fastest-growing company in the Kansas City region, benefitbay had roughly $300,000 in the bank, $400,000 in liabilities, and a board preparing to wind it down. It was 5 o’clock on a Friday when the directors handed Brandy Thompson, then the chief operating officer, their terms: Come back Monday with a survival plan—the bare minimum of people the company could run on—and take 30 days to raise rescue capital. The alternative was keeping just enough staff to offboard the customers and turn out the lights. The Omaha-launched startup had burned through $4 million in its first year, hiring 33 people in three months while chasing a huge vision. “Year one, I was pretty sure we were just going to run into the wall — full speed, a thousand miles an hour,” Thompson recalls. The board removed the founding CEO and turned to Thompson, a Kansas City finance executive whose résumé ran through Visit KC and NetStandard—and who had never raised a dime. “I’ve never led sales, I’ve never raised capital, I don’t have wealthy friends and family,” she told them. Their answer, as she remembers it: We believe in you. You’re a great storyteller, and there’s nothing to lose. Let’s give it a try. She built a deck and pitched her head off for three weeks. On day 26 of 30, a bite: Scott Shane, a Case Western Reserve professor of economics and an entrepreneurship guru himself, whose fund was named, fittingly, Comeback Capital. The $500,000 lifeline came on bruising terms—a 10-to-1 stock split, and 90 days without pay for the executives, to prove they were all-in. Thompson took the CEO seat, stretched the money six months, then landed Invest Nebraska—whose $250,000 required her to match it with angel money in 60 days. What she was rescuing was a bet on ICHRA—the defined-contribution model that lets employers fund fixed health-care dollars while employees choose their own coverage. Benefitbay’s mission was building exclusively for brokers while competitors sold direct to employers at fatter margins. “Investors were saying, ‘She’s going the wrong way,’” Thompson says. But the math was leverage, not margin: “We find one agent, we have a champion. We find one agency, we have thousands of champions.” With only three salespeople until this year, broker-partners did the selling — starting with savvy Northeast agencies that rivals avoided. Those firms were acquired into national brokerages, seeding ICHRA expertise inside the giants. In March 2023, Thompson brought the company home to Kansas City, where remote job postings drew hundreds of applicants, Hub International lent office space the budget couldn’t cover, and KC Rise tracked the company for two years before investing ahead of its Series A. The reference ladder climbed from 20-life employers to 300, to 1,000, to enterprise accounts—with one executive telling peers that Thompson’s team had saved it $1.5 million. Revenue followed as did hiring. Only halfway through 2026, the company now has 100 employees. The next hurdle? “Scale—the messy middle,” she says. But she isn’t shy about the ceiling: “benefitbay with a B—a billion. We’ll put it out there.”

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I ngr am ’ s

Kansas City’s Business Media

July 2026