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Overview: 

If you’re looking for the stability of a profitable, growing company with the entrepreneurial spirit of a startup, we’re hiring. SageSure, a leader in catastrophe-exposed property insurance, is seeking a Senior Director, Commercial Underwriting to shape and advance our commercial property strategy. This is a pivotal leadership role responsible for setting underwriting vision, ensuring operational excellence, and developing a high-performing team across our Commercial Property lines. The Senior Director will be accountable for managing complex middle-market portfolios, making proactive product and pricing recommendations, and driving profitable growth while maintaining underwriting rigor and responsiveness. 

As the most senior Company leader based in our Tampa office, this individual will also serve as a site leader and culture champion, anchoring our local presence, strengthening talent engagement, and modeling our values to enhance the employee experience. 

This role will be onsite for a minimum of 3 days a week in our Tampa, FL office.   

What you’d be doing: 

• Set the underwriting vision and strategy in collaboration with executive leadership and align team priorities to meet profitability, growth, and customer experience goals. 
• Lead and manage a team of underwriters, fostering a culture of accountability, high performance, and continuous development. 
• Oversee underwriting guidelines and pricing models, ensuring decisions are data-driven, analytically sound, and aligned with company objectives and regulatory standards. 
• Drive innovation in underwriting policies, workflows, and automation in partnership with product, actuarial, and technology teams. 
• Utilize reporting tools and data analysis to monitor portfolio performance, evaluate risk trends, and lead strategy shifts based on business needs and market changes. 
• Own portfolio management by proactively shaping product and pricing recommendations that ensure competitiveness and profitability, and partner with Sales on deeper agency management strategies to strengthen producer relationships. 
• Serve as an escalation point for complex underwriting issues and mentor senior underwriters in technical and decision-making acumen. 
• Actively monitor and interpret market and competitor trends, adjusting strategies to capitalize on opportunities or mitigate risks. 
• Lead cross-functional projects and represent underwriting in product launches, technology rollouts, or operational transformations. 
• Continuously evaluate underwriting processes and workflows, identifying opportunities for automation, efficiency improvements, and enhanced customer experience 
• Champion a strong compliance culture and ensure consistent adherence to underwriting guidelines, documentation standards, and regulatory requirements. 
• Cultivate relationships with key brokers, producers, and agency partners to support growth and service standards. 

We’re looking for someone who has: 

• 12+ years of underwriting experience in Commercial Property lines with at least 5 years in underwriting leadership  
• Deep expertise in middle market commercial property insurance, including risk analysis, catastrophe modeling, coverage structuring, and state-specific underwriting nuances (Florida experience highly preferred; experience across multiple states a strong plus). 
• Demonstrated success managing portfolios requiring customized policy terms/conditions, larger property schedules and values, and more complex underwriting and pricing analyses. 
• Proven ability to lead and develop underwriters at various levels, including technical mentoring and performance coaching. 
• Strong analytical mindset with experience using data and tools to make risk decisions, portfolio recommendations, and pricing strategies. 
• Track record of implementing process improvements, underwriting policies, or technology solutions. 
• Excellent cross-functional communication skills and experience partnering with other departments.  
• Proficient in Microsoft Office, Google Workspace, and underwriting systems/tools. 

Highly preferred candidates also have: 

• CPCU and or Property/Casualty Insurance Agent.    

About the Underwriting Team at SageSure: 

SageSure's collaborative team of underwriters works together to impact strategic decisions at the core of the business. Senior leadership customarily communicates market trends and insights with everyone on the team and is always available to discuss the philosophy of underwriting at SageSure. With a clear career path and outstanding performance, you can advance from underwriter to senior underwriter, lead underwriter, underwriting supervisor, and underwriting manager—all with compensatory bonuses. At SageSure, we want you focused on underwriting, so a dedicated team of policy services associates responds to calls and collaborates with underwriting on crucial cases. You'll be encouraged to make independent decisions and invited to work cross-functionally with other teams, including marketing, software, and product implementation. A comprehensive training curriculum begins on day one, so you're ready to start assessing risks and doing your part to help our customers protect their American Dream.