Regional Underwriting Manager – Middle Market Retail Property & Casualty

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.

Starr is a global insurance and investment organization providing property and casualty insurance solutions to business and industry, and one of the fastest-growing insurance companies in the world. Our talented and experienced associates manage risk and ultimately support the profitable growth of organizations in a dynamic, competitive and ever-changing marketplace. Join us and become part of our talented and passionate workforce. https://starr.com/About/Careers