Senior Underwriter

We are a fast-growing, tech-enabled MGA focused on providing tailored property insurance solutions for Condominium and Homeowner Associations throughout Florida. Our offerings are designed to address the needs of independent agents and brokers by delivering responsive underwriting, clear communication, and competitive products, while maintaining a strong commitment to service and operational excellence. Our leadership team consists of experienced insurance professionals with deep expertise in underwriting, operations, and distribution. Crestwell operates with a lean, collaborative structure that values flexibility, accountability, and growth. As a Senior Underwriter, you will play a critical role in driving profitable growth, strengthening agency relationships, and helping develop the underwriting team as Crestwell continues to expand. Position Summary The Senior Underwriter is responsible for driving profitable growth through disciplined risk selection, portfolio management, and agency relationship development across Crestwell's commercial residential property programs. This role evaluates and prices new and renewal business, supports underwriting strategy, mentors underwriting staff, and helps develop scalable underwriting processes and best practices. Preference will be given to candidates with experience underwriting commercial property risks, particularly condominium associations, homeowners associations, and other commercial residential exposures. The ideal candidate combines strong technical underwriting expertise with sound judgment, leadership capabilities, and the ability to thrive in a fast-paced, entrepreneurial environment. Key Responsibilities Underwriting & Risk Selection Review, evaluate, and underwrite new business, renewal business, and endorsements within established underwriting authority Analyze submissions, loss history, catastrophe exposure, inspections, and supporting documentation to assess risk acceptability Develop pricing, coverage terms, conditions, and recommendations consistent with underwriting guidelines and profitability objectives Issue quotes, negotiate terms with agents and brokers, and manage accounts through binding Agency & Broker Relationship Management Build and maintain strong relationships with agency partners and brokers Provide responsive service and underwriting guidance to support agency growth and retention Communicate appetite, underwriting requirements, and coverage solutions effectively Participate in agency meetings, marketing initiatives, and business development activities as needed Leadership & Team Development Serve as a mentor and technical resource for Underwriters and Underwriting Assistants Assist with onboarding, training, and ongoing development of underwriting staff Promote underwriting consistency, accountability, and best practices across the organization Support leadership in fostering a collaborative, high-performance underwriting culture Underwriting Strategy & Operational Excellence Contribute to the development and refinement of underwriting guidelines, procedures, and workflows Partner with operations, technology, and leadership teams to identify process improvements and enhance scalability Support carrier, reinsurance, regulatory, and internal reporting initiatives as needed Participate in special projects involving product development, system enhancements, and operational growth Qualifications Strong understanding of commercial property underwriting principles and risk analysis Demonstrated ability to evaluate and price complex risks independently Experience mentoring, coaching, or developing underwriting staff Ability to manage multiple priorities in a fast-paced start-up environment Experience working with catastrophe-exposed property business Nice to Have Direct experience in Florida commercial property markets Commercial residential property experience, including condominium and HOA programs Comfortable learning new systems and processes What We Offer Competitive compensation package with benefits Growth opportunities and career path development in underwriting A fast-paced, entrepreneurial environment with high visibility and impact Success Looks Like (30/60/90) 30 days Develop a strong understanding of Crestwell’s underwriting appetite, agency relationships, systems, and workflows. 60 days Independently manage a profitable underwriting portfolio while supporting team development and process improvements. 90 days Serve as a trusted underwriting leader, contribute to strategic initiatives, and help establish scalable underwriting practices that support continued growth. #J-18808-Ljbffr Crestwell Underwriters