Regional Underwriting Manager – Middle Market Retail Property & Casualty

Starr Insurance•Chicago, IL

About The Position

The Chicago Regional Underwriting Manager will lead Starr’s Middle Market underwriting strategy and execution across the Midwest region. The role is responsible for profitable growth, underwriting excellence, broker engagement, and team development. It combines technical underwriting leadership with an outward-facing market presence, strengthening Starr’s position with key brokers while developing a high-performing underwriting team. The manager will develop regional underwriting strategies and goals, oversee risk selection and portfolio performance, build broker relationships, and represent Starr in the Midwest marketplace. The role also partners with internal functions and ensures underwriting activity follows company authorities, guidelines, compliance requirements, and regulatory standards.

Requirements

Deep knowledge of Middle Market Retail property and casualty 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 and a track record of developing underwriters and building high-performing teams.
Ability to balance underwriting judgment, analytics, and market opportunity in decision-making.
Strong communication and collaboration skills, including the ability to influence across functions and levels.
Outward-facing, entrepreneurial mindset and confidence representing Starr in the marketplace.
Commitment to continuous improvement, innovation, and delivering a strong broker and client experience.

Responsibilities

Drive profitable growth in the Midwest through disciplined underwriting, portfolio management, and execution against business objectives.
Develop and execute regional underwriting strategies, setting production, profitability, retention, and portfolio goals.
Build and deepen broker relationships across the Midwest, identifying opportunities for profitable new and renewal business.
Lead underwriting excellence through risk selection, pricing discipline, portfolio management, and data-driven decision-making.
Lead, coach, and develop the underwriting team and foster a collaborative, accountable, high-performance culture.
Partner 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 underwriting and growth strategies.
Maintain underwriting governance and adherence to Starr’s underwriting authorities, guidelines, compliance requirements, and regulatory standards.
Represent Starr in the Midwest marketplace and strengthen its visibility and reputation with brokers, clients, and industry partners.