Assoc Mgr Underwriting

Progressive Insurance; Indiana; Remote; USD 90,000 - 120,000; Full time

Benefits offered by this job

Gainshare incentive

Flexible work arrangement

Job summary

Progressive Insurance is seeking an Associate Manager for Fleet & Specialty Underwriting to lead a workers’ compensation underwriting team, focusing on transportation. The role requires experience with guaranteed cost and loss sensitive accounts and strong skills in risk selection, pricing, and portfolio management.

You will lead a team of underwriters, coaching and supporting them to achieve strong performance and professional growth, while building internal and external business relationships.

Qualifications

• 3+ years of experience with guaranteed cost and loss sensitive workers’ compensation accounts.
• 4+ years of experience leading at an insurance carrier or agency

Responsibilities

• Lead and develop a team of underwriters, providing coaching, guidance, and support to drive underwriting performance and professional growth.
• Drive strong underwriting performance through risk selection, pricing, and portfolio management.
• Partner in the development and execution of underwriting strategies that support profitable growth and operational excellence.

Skills

Underwriting leadership

Workers’ comp underwriting

Job description

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).