Senior Commercial Underwriting Manager - Jacksonville, FL

Senior Commercial Underwriting Manager
Jacksonville, Florida | On-Site 

Join our collaborative team where you will have meaningful opportunities for growth and advancement. Our small, nimble structure means your experience will be rewarded with autonomy and the ability to impact results. Enjoy a positive, friendly work environment with accessible leadership.

Why Stillwater? 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. 

We are seeking a Senior Commercial Underwriting Manager to lead commercial underwriting operations, portfolio performance, and underwriting team development. This role is responsible for driving profitable growth through disciplined underwriting practices, effective risk management, operational excellence, and strong agency relationships.

The Senior Commercial Underwriting Manager will oversee underwriting staff, guide complex risk decisions, monitor portfolio results, and partner with executive leadership to execute strategic growth initiatives while maintaining underwriting profitability.

The Opportunity

This position offers the opportunity to play a key leadership role within a growing organization where decisions are made quickly and contributions are highly visible. The ideal candidate is both strategic and hands-on, capable of balancing team leadership with execution and operational oversight.

Unlike larger organizations with multiple layers of management, this role provides direct interaction with senior leadership and the ability to make a meaningful impact across the business.

What You’ll Do:

Program & Operational Leadership

• Lead day-to-day management of underwriting commercial programs and operational initiatives.
• Oversee workflow execution, process improvement efforts, and service delivery standards.
• Monitor program performance metrics and identify opportunities for operational enhancement.
• Support implementation of new initiatives, products, and business strategies.
• Ensure projects and deliverables are completed efficiently and aligned with organizational goals.

Product & Portfolio Management

• Oversee the end-to-end evaluation of targeted new and renewal commercial business, ensuring compliance with established risk appetites.

• Collaborate with actuarial, claims, and product teams to design, launch, and refine commercial coverage forms and product offerings.

• Identify areas of concern regarding loss ratios and risk trends, applying strategic remediation.

Pricing Strategy & Execution

• Develop, implement, and monitor pricing models, tools, and methodologies to ensure competitive yet profitable rates across all segments. 

• Review terms, and conditions for high-value and complex accounts. 

• Monitor competitive landscape and legislative/regulatory changes to adjust pricing strategies and product guidelines proactively.

Team Leadership & Development

• Manage and mentor small commercial underwriting operations and product management team.
• Foster a collaborative, accountable, and high-performing work environment.
• Provide coaching, performance feedback, and professional development support.
• Help establish priorities, allocate resources, and improve team effectiveness.

Cross-Functional Collaboration

• Partner with leadership, claims, operations, compliance, analytics, and distribution teams to support business objectives.
• Coordinate across departments to improve communication, execution, and customer experience.
• Assist with vendor, agency, and partner relationships as needed.
• Support strategic initiatives and operational planning efforts.

Process Improvement & Business Support

• Identify opportunities to streamline workflows and improve operational efficiency.
• Assist in developing reporting, tracking, and performance management tools.
• Support change management and continuous improvement initiatives.
• Help ensure compliance with company standards, regulatory requirements, and internal processes.

What We’re Looking For

• 10 years of experience in commercial underwriting insurance operations, program management, or business leadership within the P&C industry.
• Prior leadership experience managing or mentoring a small team.
• Strong organizational, project management, and operational leadership skills.
• Ability to manage multiple priorities in a fast-paced environment.
• Excellent communication and relationship-building skills.
• Strong analytical and problem-solving abilities.
• Experience working cross-functionally with multiple business units.
• Bachelor’s degree preferred; insurance industry designations are a plus.

Why This Role Is Different

• High visibility within a growing organization
• Opportunity to lead meaningful operational initiatives
• Collaborative and entrepreneurial culture
• Direct impact on business performance and growth
• Leadership role with hands-on involvement

Compensation & Benefits

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

Apply today to start your journey of being celebrated and valued with Stillwater Insurance Group.

Offer for employment contingent upon the acceptable responses from both a background investigation and a pre-employment drug screen.

Stillwater Insurance Group is a drug-free workplace and an equal opportunity employer.