Shepherd Insurance has hired Matt Kleymeyer (pictured) as president of its employee benefits division. The appointment reflects broader investment in dedicated benefits leadership at independent agencies as employer-sponsored healthcare costs approach their steepest rise in 15 years.
Kleymeyer brings nearly 20 years of employee benefits experience to the Carmel, Indiana-based firm. His career has spanned sales, client service, operations, and leadership across both small and large group markets.
Before joining Shepherd, Kleymeyer served as area executive vice president and Indiana market leader at Gallagher. He took on that role after growing and selling an employee benefits agency he co-founded. That path is one more experienced benefits practitioners are taking, drawn to independent platforms with long-standing client relationships and room to lead.
In his new role, Kleymeyer will work with benefits leadership team members Steve Gregory, Shannon Russell, and Susie Brancheau. His focus will include strategic growth, talent development, carrier relationships, and expanding Shepherd's benefits offerings.
"What drew me to Shepherd is the caliber of people already here and the strength of the relationships they've built over decades with the clients they serve," Kleymeyer said. "I'm looking forward to working alongside this team to build on that foundation and position the employee benefits practice for the next chapter of growth."
Quinn Shepherd, CEO of Shepherd Insurance, said Kleymeyer would help drive both operational improvements and strategic expansion at the firm.
The hire comes as the benefits market grows harder to manage. Healthcare costs for employer-sponsored plans are projected to rise between 6.5% and 9.5% in 2026, according to surveys from Mercer, PwC, and Aon. That range represents the largest projected increase in roughly 15 years.
A 2025 Broker Services Survey by Zywave found that balancing competitive benefits with rising healthcare costs is now employers' top HR concern. Employers are looking for advisors who can manage both cost and workforce strategy at once, rather than simply renewing coverage on price.
A LIMRA and Ernst & Young study of 800 US employers found that brokers are taking on a more strategic advisory role in benefits. The same study found that talent availability has become a constraint, and that consolidation among larger firms may reduce innovation in the sector.
