Head of Product

• →Remote First Work Environment (US Based)

• →Medical, Dental, Vision

• →401K, 401K Match

• →Life and Disability Benefits

• →Unaccrued Paid Time Off

• →11 Paid Holidays

• →Employee Discounts

• →Employee Assistance Program

• →Educational Assistance Program

• →Employee Referral Program

• →Paid Parental Leave

We are a commercial insurance Program Administrator focused on building and scaling specialty Insurance Programs. As part of our next stage of growth, we are transitioning from reliance on third-party software and SaaS vendors toward developing and owning more of the technology that powers our business.

We are building a technology organization that combines deep insurance expertise with modern software development, data, automation, and artificial intelligence. Our goal is to create differentiated platforms and tools that improve underwriting, distribution, operations, program launch speed, portfolio management, and the overall experience of our brokers, carriers, and internal teams.

We are seeking an entrepreneurial and highly experienced Head of Product to lead the creation of our product organization and technology product strategy.

This person will be responsible for identifying the highest-value opportunities for technology, AI, data, and automation across the enterprise, translating those opportunities into a prioritized product roadmap, and building the teams and operating model required to execute it.

The Head of Product will work closely with the CEO, executive leadership, underwriting, claims, actuarial, operations, distribution, finance, legal, compliance, and engineering. The role will initially be both strategic and hands-on, requiring someone who can establish the product vision while also driving early product decisions, hiring, prioritization, and delivery.

The ideal candidate has experience in AI-enabled software development, enterprise or B2B product management, and building high-performing product teams. Experience in property and casualty insurance is strongly preferred.

This is an opportunity to build a product and technology organization at the foundation of a growing insurance company. The person in this role will have meaningful influence over the company’s future operating model, technology architecture, AI capabilities, customer experience, and competitive position.

The Head of Product will not simply manage an existing product portfolio. This individual will help define what the company becomes: a modern insurance Program Administrator with the technology, data, and AI capabilities to build and scale Programs more effectively than traditional market participants.

• Develop and lead the company’s overall internally built product strategy, as well as AI software strategy.
• Establish a clear product vision aligned with the company’s business strategy and long-term competitive objectives.
• Identify opportunities to replace, improve, or integrate third-party systems through internally developed technology.
• Create a multi year product roadmap designed to implement agentic AI across all MGA's in the portfolio, through a combination of in house technology and vendors
• Define the principles, governance, and decision-making processes that will guide product development.
• Help determine which capabilities should be built internally, purchased, integrated, or developed through strategic partnerships and oversee operation of those related to AI.

• Develop a deep understanding of how our Programs are originated, designed, launched, underwritten, distributed, administered, and managed.
• Partner with business leaders to identify the most important technology opportunities across the insurance lifecycle.
• Develop tools and platforms that support underwriting workflows, submission management, appetite and eligibility decisions, pricing, portfolio oversight, broker engagement, reporting, and program administration.
• Identify ways AI can improve decision-making, productivity, knowledge management, risk selection, service, and operational efficiency.

• Establish a practical and commercially focused AI product strategy.
• Identify and prioritize high-value use cases for generative AI, machine learning, predictive analytics, intelligent automation, and decision-support tools.
• Develop appropriate standards for data quality, model governance, security, privacy, explainability, and human oversight.
• Work with engineering, data, underwriting, actuarial, legal, compliance, and risk leaders to move AI initiatives from experimentation into production.

• Build and lead a high-performing product organization, initially hiring key product leaders and individual contributors.
• Define the appropriate product organization structure, including product management, product design, user research, data product management, and product operations.
• Identify talented employees in existing departments who may be well suited for product roles and create effective pathways for their transition.

• Serve as the senior executive voice for product strategy and technology-enabled business transformation.
• Regularly communicate product priorities, progress, risks, and tradeoffs to the CEO, executive team, and Board as appropriate.
• Help shape the company’s broader technology strategy in partnership with the Chief Technology Officer

• Assess the company’s existing systems, vendor relationships, data capabilities, workflows, and technology gaps.
• Develop and secure alignment around a company-wide product and AI strategy.
• Establish a prioritized product roadmap tied to measurable business outcomes.
• Define the future product organization and begin hiring key team members.
• Identify and launch a limited number of high-impact technology or AI initiatives.
• Create the product management operating model and core development processes.
• Establish clear criteria for build-versus-buy decisions.
• Build strong working relationships with business leaders and transferred employees.
• Demonstrate measurable progress in speed, efficiency, underwriting capability, distribution effectiveness, user experience, or program-launch capacity.

• Significant experience leading product management for software, technology, AI, data, or digital platforms.
• Demonstrated experience building and scaling product organizations and teams.
• Experience taking products from concept through development, launch, adoption, and ongoing improvement.
• Experience with artificial intelligence, machine learning, generative AI, analytics, or intelligent automation.
• Experience translating complex business problems into clear product strategies and roadmaps.
• Experience operating in a complex, regulated, or highly data-driven industry.
• Strong executive communication, influencing, decision-making, and organizational leadership skills.
• Entrepreneurial mindset and willingness to operate strategically and tactically.

• Experience in property and casualty insurance, including underwriting, program administration, distribution, claims, actuarial, or insurance operations.
• Experience with MGAs, Program Administrators, carriers, reinsurers, or insurance platforms.
• Experience building products for commercial insurance or other complex B2B markets.
• Experience building products subject to regulatory, privacy, security, model-risk, or compliance requirements.
• Experience managing product teams during a period of rapid growth or organizational transformation.

The successful candidate will be:

• A builder who enjoys creating teams, processes, and products from an early stage.
• Commercially minded and able to connect technology investments to business results.
• Comfortable working in an environment where priorities evolve and not every answer is known in advance.
• Credible with both technical professionals and insurance executives.
• Curious about how insurance works and motivated by the opportunity to improve it.
• Decisive, analytical, collaborative, and highly accountable.
• Capable of balancing long-term platform development with near-term business needs.
• Focused on practical AI adoption, not simply experimentation or industry hype.
• An excellent communicator who can create alignment across departments.
• Energized by the opportunity to help shape the future of the company.

The Head of Product will report to the Chief Executive Officer and will work closely with the executive leadership team and leaders across underwriting, distribution, operations, actuarial, claims, finance, legal, compliance, engineering, and data.

• Requires a quiet work environment with regular sitting at a computer for extended periods of time.
• Occasional walking and standing, and lifting of up to 10 lbs.
• Regular use of hands and fingers.
• Frequent talking or hearing.
• Vision requirements: Close, distance, color, peripheral, focus and depth perception.