Head of Commercial Underwriting

JCW Group; Chicago (IL); On-site; USD 100,000 - 150,000; Full time

Job summary

JCW Group is seeking an experienced leader to take ownership of a specialty P&C carrier's small commercial franchise in Chicago. This role involves full P&L accountability, shaping underwriting and pricing strategies, and building a dedicated team.

The successful candidate will have a strong background in small commercial insurance, ideally with experience in BOP, commercial packages, and a P&L ownership mindset. If you are ready to build and lead this franchise, JCW Group wants to hear from you!

Qualifications

• Significant experience in small commercial insurance.
• Proven success in P&L management.
• Ability to build and scale a commercial book.

Responsibilities

• Own full P&L accountability including key financial metrics.
• Shape underwriting, pricing, and distribution strategy.
• Build a dedicated team and operating model.

Skills

Strong small commercial background — BOP, commercial package, CPP

P&L ownership mindset

Comfortable leading through influence

Job description

JCW is partnering with a specialty P&C carrier that's making a serious, funded investment in its small commercial franchise. You'll own the P&L from day one, shape strategy across underwriting, pricing, and distribution, and over time stand up a dedicated team and operating model around you. Not a maintenance role. Not a functional seat. A franchise to build.

What you’ll own

• Full P&L accountability including GWP, loss ratio, combined ratio, growth
• Appetite, pricing direction, and underwriting framework
• Distribution strategy and producer segmentation
• Organizational build‑out across a phased roadmap

What they’re looking for

• Strong small commercial background — BOP, commercial package, CPP
• Workers comp and/or commercial auto experience a significant plus
• P&L ownership mindset — carrier, MGA, or equivalent
• Track record of building, scaling, or transforming a commercial book
• Comfortable leading through influence before formal authority