Sentry employs roughly 2,650 people, making it one of the larger insurance and financial-services organizations headquartered in the Midwest. Recent headcount data shows a net gain of one employee, with seven hires and six departures, indicating a stable workforce. The company maintains a diversified talent base spanning corporate functions, technology, and client-facing roles, which supports its mix of insurance, retirement, and investment products.
Finance and Administration represents the largest share of employees at 19 %, closely followed by Sales and Support at 18 % and Engineering at 18 %. Business Management teams account for 14 % of headcount, while Marketing and Product contribute roughly 10 %. Operations, Human Resources, and Information Technology collectively add another 14 %, and smaller Consulting and miscellaneous groups round out the roster. Hiring and attrition numbers are both in the single digits, underscoring steady staffing levels across these functions.
About one-third of the workforce is based in Sentry’s longtime home of Stevens Point, Wisconsin. Additional concentrations appear in Madison, Plover, Wisconsin Rapids, Mosinee, and several other Midwest communities, reflecting the company’s regional roots. A sizable contingent—just over half of all employees—is distributed among numerous smaller offices and remote setups classified as “Other,” giving the organization nationwide reach. Phoenix, Goldsboro, Davenport, and Freeport each host modest employee counts that support localized customer and operational needs.