Assoc Mgr Underwriting

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.

Application Process If you decide to apply, you must talk with your manager and complete the following:

  • Update your internal resume and attach it to your profile along with your last two annual performance evaluations.
  • Review the minimum requirements listed under Education and/or Experience section in the internal job description and the preferred skills/experience listed below.
Your ability to be considered for an interview may be impacted by the size of the candidate pool and those who possess the preferred qualifications listed.

Additional Criteria To Confirm

  • You meet the minimum requirements listed under Education and/or Experience section.
  • Your last annual performance evaluation was no less than an overall “Successful”.
  • You’re not currently on any type of performance warning or short-term objectives.
  • You’re not currently on any type of behavioral or attendance warning.
  • You’ve been in your role for at least 12 months. Note: Some business areas may only require six months. Check with your HR consultant to confirm the appropriate requirement for your current business area.
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).
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Common Interview Questions And Answers

1. HOW DO YOU PLAN YOUR DAY?

This is what this question poses: When do you focus and start working seriously? What are the hours you work optimally? Are you a night owl? A morning bird? Remote teams can be made up of people working on different shifts and around the world, so you won't necessarily be stuck in the 9-5 schedule if it's not for you...

2. HOW DO YOU USE THE DIFFERENT COMMUNICATION TOOLS IN DIFFERENT SITUATIONS?

When you're working on a remote team, there's no way to chat in the hallway between meetings or catch up on the latest project during an office carpool. Therefore, virtual communication will be absolutely essential to get your work done...

3. WHAT IS "WORKING REMOTE" REALLY FOR YOU?

Many people want to work remotely because of the flexibility it allows. You can work anywhere and at any time of the day...

4. WHAT DO YOU NEED IN YOUR PHYSICAL WORKSPACE TO SUCCEED IN YOUR WORK?

With this question, companies are looking to see what equipment they may need to provide you with and to verify how aware you are of what remote working could mean for you physically and logistically...

5. HOW DO YOU PROCESS INFORMATION?

Several years ago, I was working in a team to plan a big event. My supervisor made us all work as a team before the big day. One of our activities has been to find out how each of us processes information...

6. HOW DO YOU MANAGE THE CALENDAR AND THE PROGRAM? WHICH APPLICATIONS / SYSTEM DO YOU USE?

Or you may receive even more specific questions, such as: What's on your calendar? Do you plan blocks of time to do certain types of work? Do you have an open calendar that everyone can see?...

7. HOW DO YOU ORGANIZE FILES, LINKS, AND TABS ON YOUR COMPUTER?

Just like your schedule, how you track files and other information is very important. After all, everything is digital!...

8. HOW TO PRIORITIZE WORK?

The day I watched Marie Forleo's film separating the important from the urgent, my life changed. Not all remote jobs start fast, but most of them are...

9. HOW DO YOU PREPARE FOR A MEETING AND PREPARE A MEETING? WHAT DO YOU SEE HAPPENING DURING THE MEETING?

Just as communication is essential when working remotely, so is organization. Because you won't have those opportunities in the elevator or a casual conversation in the lunchroom, you should take advantage of the little time you have in a video or phone conference...

10. HOW DO YOU USE TECHNOLOGY ON A DAILY BASIS, IN YOUR WORK AND FOR YOUR PLEASURE?

This is a great question because it shows your comfort level with technology, which is very important for a remote worker because you will be working with technology over time...

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