Head of Product Management and Underwriting - Jacksonville, FL

About the Company

Stillwater Insurance Group is an admitted, AM Best and Demotech rated, mid-sized P & C insurance company offering a variety of home, auto, and commercial insurance products in a 50-state US market. We are headquartered in Jacksonville, Florida, with additional offices in New York and Omaha, Nebraska. Our employees consistently describe Stillwater as a great company with great people where honesty and integrity are high priorities. As a Stillwater team member, you will make a difference every day, help grow the company, and interact with emerging technologies. Coaching and development, recognition, and professional growth are some of the benefits of working in our small team environment. Our size creates unique opportunities for employees to gain broad exposure, make meaningful contributions, and have a direct impact on company results. We value innovation, accountability, professional growth, and the relationships we build with our agents, policyholders, and employees.

About the Role

The Head of Product Management and Underwriting serves as a key leader within the Commercial organization and is responsible for the overall performance, profitability, and operational effectiveness of the Commercial portfolio. This role provides leadership and direction for underwriting operations, product management initiatives, pricing strategy, agency relationships, and portfolio management while ensuring alignment with company objectives for growth and profitability. The role collaborates closely with executive leadership and cross-functional partners to evaluate market opportunities, improve business results, and support continued expansion of the Commercial business.

Responsibilities

• Commercial Underwriting Leadership
  • Lead Commercial Underwriting operations and provide strategic direction for underwriting, product management, portfolio management, and pricing initiatives.
  • Establish business priorities and ensure alignment with company growth and profit objectives.
  • Monitor portfolio performance, production results, retention, rate adequacy, and loss ratio trends.
  • Identify opportunities for profitable growth and implement corrective actions when needed.
  • Serve as a key contributor to Commercial business planning and operational strategy.
• Portfolio & Underwriting Management
  • Oversee underwriting results and ensure adherence to underwriting guidelines, risk appetite, and regulatory requirements.
  • Review and provide direction on complex or high-exposure risks.
  • Evaluate portfolio performance and emerging risk trends.
  • Recommend underwriting, pricing, and product enhancements to improve business performance.
  • Drive underwriting consistency and operational excellence across the organization.
• Product & Pricing Leadership
  • Partner with product, actuarial, claims, and executive leadership teams to develop and refine commercial products and programs.
  • Provide leadership on product design, rate strategy, underwriting guidelines, and market expansion initiatives.
  • Monitor competitive, economic, and regulatory trends and recommend strategic adjustments as needed.
  • Support innovation and development of new product and growth opportunities.
• Leadership & Talent Development
  • Lead and develop a multi-disciplinary team that includes underwriting, product management, and actuarial professionals.
  • Provide coaching, mentorship, performance management, and professional development support.
  • Foster a culture of accountability, collaboration, continuous improvement, and customer focus.
  • Develop future leadership capability within the Commercial organization.
• Agency & Relationship Management
  • Develop and maintain strong relationships with agency partners and key stakeholders.
  • Partner with distribution teams to support growth initiatives and agency engagement strategies.
  • Represent Commercial Underwriting in agency, leadership, and industry meetings when appropriate.
• Cross-Functional Collaboration
  • Partner with Claims, Actuarial, Product, Compliance, Operations, Technology, and Executive Leadership to achieve business objectives.
  • Lead or participate in strategic initiatives involving system enhancements, process improvements, product innovation, and business transformation.
  • Drive collaboration across departments to improve execution, communication, and overall business performance.

Requirements

• 10+ years of Commercial Property & Casualty underwriting experience.
• 5+ years of leadership experience within Commercial Underwriting, Product Management, Portfolio Management, or related insurance functions.
• Demonstrated success leading teams and driving profitable business results.
• Experience managing complex commercial portfolios and contributing to underwriting strategy.
• Strong understanding of underwriting operations, pricing fundamentals, product development, and portfolio management.
• Experience leading cross-functional initiatives and influencing business decisions.
• Exceptional leadership, communication, relationship-building, and organizational skills.
• Strong analytical and problem-solving abilities.
• Bachelor's degree or equivalent combination of education and industry experience.

Preferred Qualifications

• Experience working within a carrier, MGA, or program business environment.
• CPCU, AU, ARM, or other industry designations.
• Experience leading managers, senior professionals, or multi-functional business teams.
• Exposure to strategic planning, product development, profitability management, and organizational leadership initiatives.

Why This Role Stands Out

• High visibility and regular interaction with executive leadership.
• Opportunity to influence underwriting, product, pricing, and portfolio strategy.
• Leadership responsibility across multiple commercial business functions.
• Direct impact on growth, profitability, and operational performance.
• Significant autonomy and decision-making authority within a collaborative and entrepreneurial environment.
• Opportunity for continued career growth as the organization expands.

Benefits

A competitive compensation package will be offered, including base salary, performance incentive opportunity, and comprehensive benefits.