{"schemaVersion":"jobsearcher.job.v1","id":"d9c93f12690d7802a8de303d","url":"https://jobsearcher.com/jobs/d9c93f12690d7802a8de303d","canonicalUrl":"https://jobsearcher.com/jobs/d9c93f12690d7802a8de303d","title":"Head of Project Management and Underwriting - Jacksonville, FL","description":"Senior Commercial Underwriting Manager (Commercial Operations, Product & Portfolio Leadership)\n\nStillwater Insurance Group\nJacksonville, Florida | On-Site\nWhy 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.\nOur 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.\n\nThe Opportunity\nStillwater is seeking a Head of Project Management and Underwriting to provide leadership across Commercial Underwriting, Product Management, Portfolio Performance, and Pricing Strategy.\nThis is a highly visible leadership role that partners closely with executive leadership to drive profitable growth, strengthen underwriting performance, enhance product offerings, and support the long-term strategic objectives of the Commercial business.\nThe successful candidate will lead a team of underwriting, product management, and actuarial professionals while balancing strategic leadership with operational execution. This position offers the opportunity to broaden organizational impact, influence key business decisions, and help shape the future direction of Stillwater's Commercial Lines operation.\n\nPosition Summary\nThe Senior Commercial Underwriting Manager serves as a key leader within the Commercial organization and is responsible for the overall performance, profitability, and operational effectiveness of the Commercial portfolio.\nThis 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.\nThe 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.\n\nWhat You'll Do\nCommercial Underwriting Leadership\nLead Commercial Underwriting operations and provide strategic direction for underwriting, product management, portfolio management, and pricing initiatives.\nEstablish business priorities and ensure alignment with company growth and profit objectives.\nMonitor portfolio performance, production results, retention, rate adequacy, and loss ratio trends.\nIdentify opportunities for profitable growth and implement corrective actions when needed.\nServe as a key contributor to Commercial business planning and operational strategy.\n\nPortfolio & Underwriting Management\nOversee underwriting results and ensure adherence to underwriting guidelines, risk appetite, and regulatory requirements.\nReview and provide direction on complex or high-exposure risks.\nEvaluate portfolio performance and emerging risk trends.\nRecommend underwriting, pricing, and product enhancements to improve business performance.\nDrive underwriting consistency and operational excellence across the organization.\n\nProduct & Pricing Leadership\nPartner with product, actuarial, claims, and executive leadership teams to develop and refine commercial products and programs.\nProvide leadership on product design, rate strategy, underwriting guidelines, and market expansion initiatives.\nMonitor competitive, economic, and regulatory trends and recommend strategic adjustments as needed.\nSupport innovation and development of new product and growth opportunities.\n\nLeadership & Talent Development\nLead and develop a multi-disciplinary team that includes underwriting, product management, and actuarial professionals.\nProvide coaching, mentorship, performance management, and professional development support.\nFoster a culture of accountability, collaboration, continuous improvement, and customer focus.\nDevelop future leadership capability within the Commercial organization.\n\nAgency & Relationship Management\nDevelop and maintain strong relationships with agency partners and key stakeholders.\nPartner with distribution teams to support growth initiatives and agency engagement strategies.\nRepresent Commercial Underwriting in agency, leadership, and industry meetings when appropriate.\n\nCross-Functional Collaboration\nPartner with Claims, Actuarial, Product, Compliance, Operations, Technology, and Executive Leadership to achieve business objectives.\nLead or participate in strategic initiatives involving system enhancements, process improvements, product innovation, and business transformation.\nDrive collaboration across departments to improve execution, communication, and overall business performance.\n\nWhat We're Looking For\nRequired Qualifications\n10+ years of Commercial Property & Casualty underwriting experience.\n5+ years of leadership experience within Commercial Underwriting, Product Management, Portfolio Management, or related insurance functions.\nDemonstrated success leading teams and driving profitable business results.\nExperience managing complex commercial portfolios and contributing to underwriting strategy.\nStrong understanding of underwriting operations, pricing fundamentals, product development, and portfolio management.\nExperience leading cross-functional initiatives and influencing business decisions.\nExceptional leadership, communication, relationship-building, and organizational skills.\nStrong analytical and problem-solving abilities.\nBachelor's degree or equivalent combination of education and industry experience.\n\nPreferred Qualifications\nExperience working within a carrier, MGA, or program business environment.\nCPCU, AU, ARM, or other industry designations.\nExperience leading managers, senior professionals, or multi-functional business teams.\nExposure to strategic planning, product development, profitability management, and organizational leadership initiatives.\n\nWhy This Role Stands Out\nHigh visibility and regular interaction with executive leadership.\nOpportunity to influence underwriting, product, pricing, and portfolio strategy.\nLeadership responsibility across multiple commercial business functions.\nDirect impact on growth, profitability, and operational performance.\nSignificant autonomy and decision-making authority within a collaborative and entrepreneurial environment.\nOpportunity for continued career growth as the organization expands.\n\nCompensation & Benefits\nA competitive compensation package will be offered, including base salary, performance incentive opportunity, and comprehensive benefits, aligned with experience.\n\nApply today to start your journey of being celebrated and valued with Stillwater Insurance Group.\n\nOffer for employment contingent upon the acceptable responses from both a background investigation and a pre-employment drug screen.\n\nStillwater Insurance Group is a drug-free workplace and an equal opportunity employer.","company":"Stillwaterinsurance","rawCompany":"stillwaterinsurance","city":"Jacksonville","state":"FL","isRemote":false,"isActive":false,"createdAt":"2026-08-13T14:09:13.040Z","occupations":[{"code":"13-2053.00","title":"Insurance Underwriters","slug":"insurance-underwriters"},{"code":"13-1082.00","title":"Project Management Specialists","slug":"project-management-specialists"},{"code":"11-1021.00","title":"General and Operations Managers","slug":"general-and-operations-managers"}],"industries":[{"code":"524126","title":"Direct Property and Casualty Insurance Carriers","slug":"direct-property-and-casualty-insurance-carriers"},{"code":"524128","title":"Other Direct Insurance (except Life, Health, and Medical) Carriers","slug":"other-direct-insurance-except-life-health-and-medical-carriers"},{"code":"524298","title":"All Other Insurance Related Activities","slug":"all-other-insurance-related-activities"}],"jobPosting":{"@context":"https://schema.org","@type":"JobPosting","title":"Head of Project Management and Underwriting - Jacksonville, FL","description":"Senior Commercial Underwriting Manager (Commercial Operations, Product & Portfolio Leadership)\n\nStillwater Insurance Group\nJacksonville, Florida | On-Site\nWhy 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.\nOur 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.\n\nThe Opportunity\nStillwater is seeking a Head of Project Management and Underwriting to provide leadership across Commercial Underwriting, Product Management, Portfolio Performance, and Pricing Strategy.\nThis is a highly visible leadership role that partners closely with executive leadership to drive profitable growth, strengthen underwriting performance, enhance product offerings, and support the long-term strategic objectives of the Commercial business.\nThe successful candidate will lead a team of underwriting, product management, and actuarial professionals while balancing strategic leadership with operational execution. This position offers the opportunity to broaden organizational impact, influence key business decisions, and help shape the future direction of Stillwater's Commercial Lines operation.\n\nPosition Summary\nThe Senior Commercial Underwriting Manager serves as a key leader within the Commercial organization and is responsible for the overall performance, profitability, and operational effectiveness of the Commercial portfolio.\nThis 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.\nThe 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.\n\nWhat You'll Do\nCommercial Underwriting Leadership\nLead Commercial Underwriting operations and provide strategic direction for underwriting, product management, portfolio management, and pricing initiatives.\nEstablish business priorities and ensure alignment with company growth and profit objectives.\nMonitor portfolio performance, production results, retention, rate adequacy, and loss ratio trends.\nIdentify opportunities for profitable growth and implement corrective actions when needed.\nServe as a key contributor to Commercial business planning and operational strategy.\n\nPortfolio & Underwriting Management\nOversee underwriting results and ensure adherence to underwriting guidelines, risk appetite, and regulatory requirements.\nReview and provide direction on complex or high-exposure risks.\nEvaluate portfolio performance and emerging risk trends.\nRecommend underwriting, pricing, and product enhancements to improve business performance.\nDrive underwriting consistency and operational excellence across the organization.\n\nProduct & Pricing Leadership\nPartner with product, actuarial, claims, and executive leadership teams to develop and refine commercial products and programs.\nProvide leadership on product design, rate strategy, underwriting guidelines, and market expansion initiatives.\nMonitor competitive, economic, and regulatory trends and recommend strategic adjustments as needed.\nSupport innovation and development of new product and growth opportunities.\n\nLeadership & Talent Development\nLead and develop a multi-disciplinary team that includes underwriting, product management, and actuarial professionals.\nProvide coaching, mentorship, performance management, and professional development support.\nFoster a culture of accountability, collaboration, continuous improvement, and customer focus.\nDevelop future leadership capability within the Commercial organization.\n\nAgency & Relationship Management\nDevelop and maintain strong relationships with agency partners and key stakeholders.\nPartner with distribution teams to support growth initiatives and agency engagement strategies.\nRepresent Commercial Underwriting in agency, leadership, and industry meetings when appropriate.\n\nCross-Functional Collaboration\nPartner with Claims, Actuarial, Product, Compliance, Operations, Technology, and Executive Leadership to achieve business objectives.\nLead or participate in strategic initiatives involving system enhancements, process improvements, product innovation, and business transformation.\nDrive collaboration across departments to improve execution, communication, and overall business performance.\n\nWhat We're Looking For\nRequired Qualifications\n10+ years of Commercial Property & Casualty underwriting experience.\n5+ years of leadership experience within Commercial Underwriting, Product Management, Portfolio Management, or related insurance functions.\nDemonstrated success leading teams and driving profitable business results.\nExperience managing complex commercial portfolios and contributing to underwriting strategy.\nStrong understanding of underwriting operations, pricing fundamentals, product development, and portfolio management.\nExperience leading cross-functional initiatives and influencing business decisions.\nExceptional leadership, communication, relationship-building, and organizational skills.\nStrong analytical and problem-solving abilities.\nBachelor's degree or equivalent combination of education and industry experience.\n\nPreferred Qualifications\nExperience working within a carrier, MGA, or program business environment.\nCPCU, AU, ARM, or other industry designations.\nExperience leading managers, senior professionals, or multi-functional business teams.\nExposure to strategic planning, product development, profitability management, and organizational leadership initiatives.\n\nWhy This Role Stands Out\nHigh visibility and regular interaction with executive leadership.\nOpportunity to influence underwriting, product, pricing, and portfolio strategy.\nLeadership responsibility across multiple commercial business functions.\nDirect impact on growth, profitability, and operational performance.\nSignificant autonomy and decision-making authority within a collaborative and entrepreneurial environment.\nOpportunity for continued career growth as the organization expands.\n\nCompensation & Benefits\nA competitive compensation package will be offered, including base salary, performance incentive opportunity, and comprehensive benefits, aligned with experience.\n\nApply today to start your journey of being celebrated and valued with Stillwater Insurance Group.\n\nOffer for employment contingent upon the acceptable responses from both a background investigation and a pre-employment drug screen.\n\nStillwater Insurance Group is a drug-free workplace and an equal opportunity employer.","datePosted":"2026-08-13T14:09:13.040Z","dateModified":"2026-08-13T14:09:13.040Z","hiringOrganization":{"@type":"Organization","name":"Stillwaterinsurance","sameAs":"https://jobsearcher.com"},"jobLocation":{"@type":"Place","address":{"@type":"PostalAddress","addressLocality":"Jacksonville","addressRegion":"FL","addressCountry":"US"}},"identifier":{"@type":"PropertyValue","name":"JobSearcher","value":"d9c93f12690d7802a8de303d"},"url":"https://jobsearcher.com/jobs/d9c93f12690d7802a8de303d"}}