People Moves: Shepherd Insurance Names Kleymeyer as President of Employee Benefits

July 24, 2026

Shepherd Insurance announced that Matt Kleymeyer has joined the firm as the President of Employee Benefits, further strengthening the organization’s commitment to delivering innovative employee benefits solutions and exceptional client service.

Based out of Shepherd’s headquarters in Carmel, Indiana, Kleymeyer brings nearly 20 years of employee benefits experience to the organization. His career has spanned nearly every facet of the business across both small and large group markets, including sales, client service, operations, and leadership.

Prior to joining Shepherd, Kleymeyer served as Area Executive Vice President and Indiana Market Leader at Gallagher, following the successful growth and sale of an employee benefits agency he co-founded. Throughout his career, Kleymeyer has built a reputation for fostering strong client relationships, developing high-performing teams, and helping organizations attract employees through benefits services.

As President of Employee Benefits, Kleymeyer will partner closely with Employee Benefits leadership team members Steve Gregory, Shannon Russell, and Susie Brancheau to help drive the continued growth and evolution of Shepherd Insurance’s benefits practice.

In this role, he will focus on strategic leadership, driving departmental growth, talent development, carrier relationships, and identifying opportunities to further enhance the firm’s employee benefits offerings.