Regional Underwriting Manager – Middle Market Retail Property & Casualty

Starr Insurance; Chicago (IL); On-site; USD 180,000 - 230,000; Full time

Job summary

Starr Insurance is seeking a Chicago Regional Underwriting Manager to lead the Middle Market underwriting strategy across the Midwest. You will drive profitable growth, oversee portfolio performance, and strengthen broker engagement while building a high‑performing underwriting team.

You will balance underwriting judgment with analytics, represent Starr in the Midwest marketplace, and collaborate with cross-functional partners to deliver outstanding broker and client experiences.

Qualifications

• Deep knowledge of Middle Market Retail P&C underwriting, pricing, and portfolio management.
• Established Chicago and Midwest broker relationships and credibility.
• Ability to drive profitable growth while maintaining underwriting discipline.
• Experience leading underwriting teams and developing talent.

Responsibilities

• Drive profitable growth for Starr’s Midwest region through disciplined underwriting and portfolio management.
• Develop and execute regional underwriting strategies with clear goals for production and profitability.
• Build and deepen broker relationships to expand Starr’s presence and win new business.
• Lead underwriting excellence with risk selection, pricing discipline, and data-driven decisions.
• Coach and develop the underwriting team to sustain a high‑performance culture.
• Collaborate across underwriting, distribution, risk control, claims, and operations.
• Monitor market conditions and translate trends into actionable growth strategies.
• Maintain governance, adherence to authorities, and regulatory standards.

Skills

Middle Market P&C underwriting

Broker relations (Chicago/Midwest)

Leadership of underwriters

Underwriting governance

Data-driven decision making

Cross-functional collaboration

Job description

Join Starr, a global leader in commercial insurance with over a century of expertise. We empower our employees to innovate, make impactful decisions, and build lasting client relationships worldwide. At Starr, you’ll work in an entrepreneurial culture alongside accessible leaders, leveraging our financial strength and vast industry experience to deliver solutions for our clients, no matter how complex. Grow your career with a rapidly growing company that invests in its people and their ability to drive real progress.

Position Overview
The Chicago Regional Underwriting Manager will lead Starr’s Middle Market underwriting strategy and execution across the region, with responsibility for driving profitable growth, underwriting excellence, broker engagement, and team development. This role will combine strong technical underwriting leadership with an outward-facing market presence, building Starr’s position with key brokers while developing a high-performing underwriting team.

Key Responsibilities

• Drive profitable growth for Starr’s Midwest region through disciplined underwriting, portfolio management, and strong execution against business objectives.
• Develop and execute regional underwriting strategies, establishing clear production, profitability, retention, and portfolio goals.
• Build and deepen broker relationships across the Midwest market, identifying opportunities to expand Starr’s presence and generate profitable new and renewal business.
• Lead underwriting excellence through effective risk selection, pricing discipline, portfolio management, and data-driven decision‑making.
• Lead, coach, and develop the underwriting team, creating a collaborative, accountable, high‑performance culture.
• Partner across Starr with underwriting, distribution, risk control, claims, operations, and other stakeholders to deliver a differentiated broker and client experience.
• Monitor market conditions and emerging trends and translate them into actionable underwriting and growth strategies.
• Maintain strong underwriting governance, ensuring adherence to Starr’s underwriting authorities, guidelines, compliance requirements, and regulatory standards.
• Represent Starr in the Midwest marketplace, strengthening the company’s visibility and reputation with key brokers, clients, and industry partners.

Your Skillset

• Deep knowledge of Middle Market Retail P&C underwriting, pricing, and portfolio management.
• Established Chicago and Midwest broker relationships and credibility in the marketplace.
• Demonstrated ability to drive profitable growth while maintaining underwriting discipline.
• Strong leadership skills with a track record of developing underwriters and building high‑performing teams.
• Ability to balance underwriting judgment, analytics, and market opportunity in making decisions.
• Strong communication and collaboration skills with the ability to influence across functions and levels.
• An outward‑facing, entrepreneurial mindset with the confidence to represent Starr in the marketplace.
• A commitment to continuous improvement, innovation, and delivering a strong broker and client experience.

Starr is an equal opportunity employer, which means we’ll consider all suitably qualified applicants regardless of gender identity or expression, ethnic origin, nationality, religion or beliefs, age, sexual orientation, disability status or any other protected characteristic. We recruit and develop our people based on merit and we’re committed to creating an inclusive environment for all employees. We offer first class training and development opportunities to all employees. Our aim is to grow our own talent and bring out the best in people.