Director of Underwriting

Olympus Insurance Company • Jacksonville, FL

7d • Onsite

About The Position

The Director of Underwriting is a strategic, influential, and hands-on leader responsible for driving underwriting excellence, portfolio profitability, and disciplined risk selection across Olympus’s homeowners’ book of business. This role champions consistent, high-quality underwriting practices that align with Olympus’s values of Service, Simplicity, and Accountability while supporting business growth in a complex and evolving P&C market.

The Director oversees the planning, coordination, and continuous improvement of underwriting operations, ensuring strong controls, clear processes, and a high-performing team equipped to deliver an outstanding agent and policyholder experience. This leader will mentor, develop, and elevate the underwriting staff, fostering technical expertise, sound judgment, and a culture of accuracy, collaboration, and forward thinking.

Requirements

• Bachelor’s degree in Business, Finance, Risk Management, or a related discipline required; advanced degree preferred.
• 10+ years of progressive underwriting experience, preferably in homeowners or property lines, with 5+ years in a leadership role.
• Demonstrated experience creating and optimizing underwriting policies, procedures, and performance controls.
• Proven success leading high-performing teams in a fast-paced, data-driven underwriting environment.
• Experience leveraging technology, analytics, and third-party data to drive decision quality.
• Strong understanding of Florida regulatory requirements and state-specific underwriting considerations.
• Strategic Thinking & Judgment: Ability to balance long-term strategy with day-to-day operational needs.
• Underwriting & Risk Expertise: Deep understanding of property risk, mitigation strategies, and regulatory requirements.
• Leadership & Talent Development: Ability to coach, mentor, and elevate technical underwriting talent.
• Operational Excellence: Skilled in process improvement, workflow management, and building scalable systems.
• Analytical Mindset: Strong ability to interpret data, identify trends, and make informed recommendations.
• Collaborative Communication: Works effectively across all levels of the organization; strong relationship-building skills with both internal stakeholders and agency partners.
• Adaptability: Thrives in a changing market, navigates ambiguity, and leads with confidence and clarity.

Nice To Haves

• Professional designations such as CPCU, ARM, AU, or ARe strongly preferred.

Responsibilities

• Lead and evaluate the Underwriting team at both a macro (strategy, performance, portfolio health) and micro (individual decision quality, technical accuracy) level.
• Design, implement, and monitor underwriting policies, procedures, and controls that ensure consistency, compliance, and profitable growth.
• Review, analyze, and elevate underwriting decisions to ensure they align with Olympus’s risk appetite, regulatory requirements, and strategic objectives.
• Provide coaching, feedback, training, and professional development opportunities to build a high-performing team with strong underwriting acumen.
• Develop and report on underwriting key performance indicators, trends, and insights for senior leadership, recommending action plans where needed.
• Collaborate with cross-functional partners including Risk, Claims, Finance, Product, and Sales/Agency Management, to ensure cohesive decision-making and support for enterprise initiatives.
• Maintain expert knowledge of Florida P&C market trends, regulatory changes, legislative impacts, and competitive dynamics to inform underwriting strategy.
• Lead and support underwriting technology initiatives, including automation, third-party data integrations, and workflow enhancements.
• Represent Underwriting in strategic discussions, special projects, audits, and cross-department meetings.
• Represent Olympus at industry conferences and meetings.

Benefits

• Employer-sponsored medical, dental, and vision plans
• Company-paid life insurance, short-term disability, and long-term disability
• 401(k) with up company match
• Paid Time Off to include annual PTO, Holidays, Floating Holidays, and Volunteer Time Off
• Education Assistance Program and ongoing professional development opportunities
• Wellness Lunch N Learns
• Employee perks such as pet insurance, discount programs, and a welcoming office environment

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Number of Employees: 11-50 employees