Head of Captives

We’re determined to make a difference and are proud to be an insurance company that goes well beyond coverages and policies. Working here means having every opportunity to achieve your goals – and to help others accomplish theirs, too. Join our team as we help shape the future.          

Reporting to the Head of Large & Complex business, the Head of Captives is a strategic and dynamic leader responsible for setting and executing the vision, strategy, and operational excellence of The Hartford’s Captives Business, including Single Parent and Group Captives, representing a significant portion of the Middle & Large Business portfolio. This role has full accountability for significant portfolio growth, profitability, rate achievement, retention, new business, and total losses, and will drive innovation and customer-centricity in alignment with enterprise goals and market trends.

Key Responsibilities:

Strategic Leadership & Business Oversight

• Develop and execute a multi-year, forward-looking product strategy and operating model for the Captives business, setting significant growth targets aligned with enterprise and segment goals, and driving appetite expansion, pricing sophistication, and service innovation.

• Manage the full P&L for the Captives portfolio, including Single Parent and Group Captives, driving growth, profitability, and operational excellence.

• Lead innovation in Captive solutions, leveraging data, analytics, and emerging technologies.

• Oversee Underwriting performance, pricing strategy, risk selection, and compliance across Captive programs.

• Partner with Claims, Risk Engineering, Actuarial, Finance, Technology, Compliance, Legal, Operations, and IT to deliver integrated solutions and support risk decision-making.

• Collaborate with Distribution and Marketing to enhance visibility, market penetration, and sales initiatives.

Customer & Market Engagement

• Build and maintain strong relationships with brokers, Captive Board of Directors, Captive managers, clients, and top agents to maximize market share and retention. High level of travel required.

• Represent The Hartford in industry forums, thought leadership platforms, and field engagements.

• Monitor competitive landscape and regulatory developments to inform strategy and anticipate market actions.

Leadership Accountabilities

• Lead, develop, and pipeline a high-performing team of Underwriting professionals.

• Foster a culture of accountability, innovation, collaboration, and continuous improvement.

• Create and sustain an engaged, inclusive, and high-performing culture through effective talent management and succession planning.

• Lead change associated with adoption of advanced technology solutions and cross-functional initiatives to improve operational efficiency and customer experience.

• Provide visible leadership internally and externally, participating in Employee Resource Groups, workplace communities, and company-wide initiatives.

• Ensure clear direction and communication to support HIG and segment initiatives.

Qualifications:

• 15+ years progressive experience in Commercial Insurance P&C underwriting, sales/field management, and supervision.

• Proven track record of leading complex portfolios and delivering profitable growth.

• Strong strategic thinking, financial acumen, and execution capabilities.

• Exceptional leadership and people development skills, with 10+ years people leadership experience.

• Technical knowledge of insurance industry operations and processes.

• Ability to navigate ambiguity and drive innovation in a changing market.

• Bachelor’s degree required; advanced degree and/or CPCU, ARM, CIC designation preferred.

• Superior analytical and problem-solving skills, including the ability to encourage new ways of looking at problems and generate new ideas for profitable growth.

• Ability to interact with the C-suite and across all levels of the organization.

• Strong industry reputation as both a technical and externally facing market leader and thought partner.

• Requires 50% travel including international.

Preferred Attributes

• Experience with digital transformation or technology-enabled underwriting.

• Strong external presence and ability to influence industry direction.

• Passion for customer-centricity and adaptive leadership.

• Demonstrated bias for speed and execution that serves shareholders and customers.

Location: (Hybrid) Preferred: Hartford, CT; Chicago, IL; New York, NY; Atlanta, GA; Los Angelas/ Brea, CA.

Compensation

The listed annualized base pay range is primarily based on analysis of similar positions in the external market. Actual base pay could vary and may be above or below the listed range based on factors including but not limited to performance, proficiency and demonstration of competencies required for the role. The base pay is just one component of The Hartford’s total compensation package for employees. Other rewards may include short-term or annual bonuses, long-term incentives, and on-the-spot recognition. The annualized base pay range for this role is:

The posted salary range reflects our ability to hire at different position titles and levels depending on background and experience.

Equal Opportunity Employer/Sex/Race/Color/Veterans/Disability/Sexual Orientation/Gender Identity or Expression/Religion/Age

About Us | Our Culture | What It’s Like to Work Here | Perks & Benefits