Field Underwriting Territory Representative - Commercial Middle Market

Are you a relationship-driven underwriter who loves being out in the field, building partnerships and making decisions that drive growth?

This is an opportunity to take ownership of your territory — and truly run it like your own business.

We’re seeking a Field Underwriting Territory Representative to oversee the Chicago market for a top-rated national carrier.

You’ll have the autonomy, resources, and support to build deep agency relationships, underwrite profitable business, and represent the company with pride — all while working 100% remotely.

• Underwrite: Analyze risks, price accounts, negotiate terms and make informed decisions across a variety of commercial lines.
• Develop Business: Grow and diversify your agency base — sell, solicit, and cross-market business across multiple divisions.
• Lead the Territory: Build and execute a strategic plan for growth and profitability; take full ownership of your market.
• Be the Partner Agents Trust: Build meaningful relationships, provide solutions and help agencies grow their book with you.
• Stay Ahead: Track trends, competitors, and emerging risks to make smart, forward-thinking decisions.

• Full autonomy — be treated like an adult professional, trusted to run your business.
• Strong compensation package with excellent benefits and a company car
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• Collaborative, high-integrity culture where people genuinely love what they do.
• Career growth within one of the most respected, stable carriers in the industry.

• 2+ years of Commercial Middle Market underwriting experience (multi-line preferred)
• Strong relationship management and communication skills
• Analytical mindset with the ability to make sound, confident decisions
• Chicago-based with willingness to travel within territory

If you’re looking for the best of both worlds — underwriting depth and client-facing autonomy — this is the role that lets you do your best work.

For more information, contact Lance Polikov at