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. What You’ll Do • 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. What’s In It for You • Full autonomy — be treated like an adult professional, trusted to run your business. • Strong compensation package with excellent benefits and a company car. • Collaborative, high-integrity culture where people genuinely love what they do. • Career growth within one of the most respected, stable carriers in the industry. What You Bring • 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 • Bachelor’s degree; professional designations (CIC, CPCU, etc.) a plus • 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 lpolikov@prs2000.com keywords: Commercial underwriter, Middle market underwriter, Field underwriter, Territory underwriter, Production underwriter, Multi-line commercial underwriting, Property casualty underwriting, P&C underwriter, Commercial lines underwriter, Agency relationships, Independent agents, Field marketing, Territory management, New business development, Account underwriting, Risk analysis, Pricing and negotiation, Agency distribution, Strategic territory planning, Portfolio profitability, Relationship management, Insurance carrier, CPCU, CIC, Underwriter, Territory Manager, Business Development, BDM, Apply tot his job Apply To this Job