NASHVILLE, TN (May 21, 2026): Bailey & Company announced today that it served as the exclusive financial advisor to benefitbay®, a leading Individual Coverage Health Reimbursement Arrangement (ICHRA) partner serving the nation’s top brokerages, employers, and their employees, on its strategic investment from Ten Coves Capital. The investment will fund the next phase of benefitbay’s growth, including continued build-out of its payments infrastructure, expansion of direct carrier and payroll integrations, and enhancements to the broker enablement tools that have made benefitbay the administrator of choice for top brokerages.
The financing comes at an inflection point for employer-sponsored health benefits. Traditional group premiums have outpaced what employers can absorb, and employees are demanding greater flexibility in their coverage, which is accelerating a structural shift from defined benefit to defined contribution healthcare. ICHRA has emerged as the leading vehicle for that shift.
As large brokerages build dedicated ICHRA practices and bring 1,000-life-and-above groups to market, benefitbay is positioned to scale alongside them. The company was founded with a deliberate broker-first strategy and now supports more than 40,000 covered lives across a national footprint of premier brokerages.
“We built benefitbay because we believe employees deserve more than a one-size-fits-no-one health plan,” said Brandy Thompson, Founder and CEO of benefitbay. “Brokers are how we make that vision real at scale, and this investment means we can go further, faster with better tools for the brokers who trust us, better infrastructure for the employers who rely on us, and better outcomes for the employees who depend on us to get it right.”
Ten Coves brings direct experience in consumer-directed healthcare, having backed HSA administrator HealthEquity (NYSE: HQY) from early growth through its 2014 IPO.
“We’ve seen firsthand that when employees are given control over their healthcare dollars, supported by the right technology and infrastructure, the model is durable and the category compounds,” said Dan Kittredge, Managing Partner of Ten Coves Capital. “ICHRA represents the next chapter of that story, and benefitbay has built the infrastructure to lead it.”
Beyond the macro tailwind, Ten Coves was drawn to three elements of benefitbay’s business: the broker channel as the durable demand aggregator for ICHRA, the company’s payments and reconciliation architecture as a meaningful technical moat, and a track record of winning and retaining large employer groups.
“What stood out to us about benefitbay is the quality of what the team has built and the conviction with which they’ve built it,” said Michael Lipin, Principal at Ten Coves Capital. “The platform reflects a deep understanding of how brokers, employers, and employees actually engage with health benefits, and that understanding shows up in the product, the partnerships, and the results. We’re thrilled to partner with this team and lock arms for their next phase of growth.”
“Over the past year, we’ve seen ICHRA grow from a niche benefits mechanism to an established cost containment strategy with growing traction among large employers,” said Rebecca Springer, Senior Director at Bailey & Company. “benefitbay has led the way in developing strong broker relationships and enterprise-grade tooling for ICHRA. We are excited to see the company partner with Ten Coves to further accelerate momentum,” added James Metcalf, Managing Director at Bailey & Company.
ABOUT BENEFITBAY
benefitbay® is a broker-first ICHRA administration partner helping employers modernize healthcare benefits through personalized, defined contribution healthcare models. The company provides enterprise-grade technology supporting plan comparison, enrollment, compliance, payroll integration, payments infrastructure, carrier connectivity, and employee education. benefitbay works with employers, brokers, carriers, and employees nationwide to simplify and scale consumer-driven healthcare solutions. For more information, visit www.benefitbay.com.
ABOUT TEN COVES CAPITAL
Ten Coves Capital backs high-growth companies across the FinTech ecosystem where its capital, network, and decades of experience can help accelerate growth and value creation. Investing across payments, banking & lending, asset management, capital markets, and insurance & benefits (among other segments), the Ten Coves team has helped scale over 40 companies that are solving industry pain points, enabling workflows, and providing critical infrastructure to the largest financial institutions down to SMBs. For more information, visit tencoves.com.
CONTACT INFORMATION
James Metcalf
Co-Head of Healthcare Services & Managing Director
Bailey & Company is a Nashville-based merchant banking platform focused on middle market healthcare companies in the healthcare services, healthcare technology, payer services and pharma services/medtech/life sciences sectors. As one of the largest independent, sector-focused investment banking and investing platforms in the country, Bailey & Company supports strong management teams that have built scalable platforms by providing strategic insights, world-class advice and access to one of the most diverse networks of industry experts. For more information see: www.bnco.com
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