Position Summary:
The Associate Manager, Progressive’s Fleet & Specialty Underwriting is responsible for leading the day-to-day operations of a workers’ compensation underwriting team focused on the transportation industry. This role requires prior experience underwriting both guaranteed cost and loss sensitive workers’ compensation accounts, and candidates should bring a strong understanding of risk selection, pricing, and portfolio management within these products.
In this position, the Associate Manager will lead and develop a team of underwriters, providing coaching, guidance, and support to drive strong underwriting performance and professional growth. The role also requires strong critical thinking and sound decision-making skills, as well as the ability to build and maintain effective internal and external business relationships.
The Associate Manager will partner in the development and execution of underwriting strategies that support profitable growth, operational excellence, and continued expansion of the transportation book of business.
Preferred Skills/Experience
3+ years of experience with guaranteed cost and loss sensitive workers’ compensation accounts.
4+ years of experience leading at an insurance carrier or agency
Miscellaneous Information
Location: Countrywide
Compensation: $89,600 - $119,500/year
Gainshare: Gainshare cash incentive up to 30% of your eligible earnings based on company performance.
Work Schedule:
Monday - Friday schedule. Work from Home with occasional travel; option for hybrid or full-time in-office depending on location. Will need to be able to work either Central or Eastern work schedule.
Posting Close Date:
Applications will be accepted through 11:59ET Monday October 19, 2026 (always subject to change).
