Agentic AI Technical Product Manager

Say hello to Hagerty 

Hagerty is a company built by drivers for drivers. We put our members at the center of everything we do and are dedicated to making it easier and more enjoyable for enthusiasts to drive and celebrate the machines they love. We’re proud to be the world’s largest insurer of collectible and enthusiast vehicles and are home to the Hagerty Drivers Club, the world’s largest car club. Our Marketplace business presents live and digital sales across the U.S. and Europe, we host a number of driving events and concours, and our award-winning automotive journalists produce the most popular car magazine globally, alongside internationally awarded videos. We’re committed to Never Stop Driving. Ready to get in the driver’s seat? Join us!  

As the Agentic AI Technical Product Manager, you will lead the development, enhancement, and continuous improvement of member-facing and agent-facing agentic experiences. 

You’ll partner closely with cross-functional teams—including Business Owners, Engineering, Design, Underwriting, Operations, and other stakeholders—to define product strategy, deliver high-quality solutions, and ensure our technology evolves to meet changing business and customer needs.

This role requires a strong product mindset, technical acumen, and the ability to operate effectively in complex, cross-functional environments.

What You’ll Do

Product Strategy & Roadmap

• Own the product vision and roadmap for Member-facing and Agent-facing Agentic AI Journeys aligning business objectives with platform capabilities and technical constraints.

• Balance business objectives, customer needs, and technical feasibility to prioritize initiatives. 

• Incorporate user feedback, market trends, and competitive insights to drive innovation and continuous improvement. 

Requirements & Feature Development

• Translate business needs and user insights into clear, developer-ready features and acceptance criteria. 

• Partner with stakeholders and subject matter experts to identify opportunities, validate solutions, and refine features. 

• Prioritize enhancements based on ROI, user impact, and delivery complexity. 

Backlog & Delivery Management

• Own and maintain a well-groomed product backlog aligned to business priorities balancing new capabilities, enhancements, and technical debt.

• Collaborate closely with Engineering and QA throughout the development lifecycle to ensure timely, high-quality delivery. 

• Participate actively in sprint planning, reviews, and retrospectives to drive continuous improvement. 

Technical Alignment

• Ensure solutions align with Hagerty best practices, architectural standards, and enterprise integration patterns

• Partner with both the business and engineering to evaluate design decisions, tradeoffs, and implementation approaches. 

• Stay current on relevant technologies, platforms, and regulatory considerations impacting product development. 

User Experience & Adoption

• Champion user-centric design principles, ensuring intuitive and effective product experiences. 

• Support product rollout through documentation, training, and internal enablement. 

• Gather feedback to continuously improve usability and adoption. 

Performance & Metrics

• Define and track KPIs and success metrics to measure product performance and business impact. 

• Use data and insights to inform prioritization, enhancements, and long-term strategy. 

Leadership & Collaboration

• Act as a product subject matter expert and trusted partner across business and technology teams. 

• Navigate ambiguity and complex tradeoffs, providing clear product direction and decision-making.

• Communicate effectively with stakeholders at all levels of the organization. 

This might describe you

• 5+ years of product management experience, preferably in a technical or SaaS environment. 

• Familiarity with generative AI and agentic AI application development.  

• Strong technical aptitude with the ability to work closely with engineering teams and understand complex systems. 

• Proven track record of owning product strategy, defining roadmaps, and delivering complex software solutions. 

• Experience translating business requirements into actionable products and technical deliverables. 

• Strong analytical and problem-solving skills with a data-driven approach to decision-making. 

• Experience working in agile development environments with a solid understanding of modern software delivery practices. 

• Excellent communication, collaboration, and stakeholder management skills. 

• A user-focused mindset with attention to detail and a passion for delivering high-quality products.

• Insurance industry experience is a plus. 

Nice to Have

• Experience with enterprise platforms or complex system integrations.

• Familiarity with tools such as Azure DevOps or similar agile delivery platforms. 

• Exposure to regulated environments or compliance-driven product development (e.g., SOX). 

You’ll Thrive Here If You…

• Have technical product expertise and enjoy owning complex, mission-critical systems.

• Are comfortable operating at the intersection of product, technology, and finance.

• Prefer clarity and precision over vague product language.

• Enjoy turning messy operational problems into scalable platform capabilities.

Other things to note 

• This position is open to U.S. remote work. However, team members who reside within 20 miles of the Traverse City headquarters will follow a hybrid schedule, working from the office three days per week. 

• May require travel for quarterly events.  

• Familiarity with public company requirements, including Sarbanes Oxley and key regulations, if applicable. For SOX compliant roles, responsible for designing, executing, and documenting internal controls where they have been identified as owners to prevent errors in financial reporting, processes, and business operations. Including attestation to the completeness, accuracy, and compliance of all financial reporting data, where applicable. 

If you reside in the following jurisdictions: Illinois, Colorado, California, District of Columbia, Hawaii, Maryland, Minnesota, Nevada, New York, or Jersey City, New Jersey, Cincinnati or Toledo, Ohio, Rhode Island, Washington, British Columbia, Canada please email [email protected] for compensation, comprehensive benefits and the perks that set us apart.  

At Hagerty, we share the road. We are an inclusive automotive community where all are welcomed, valued and belong regardless of race, gender, age, or car preference.  We are united by our shared passion for driving, our commitment to preserve car culture for future generations and our desire to make a positive impact in the world. 

#LI-Remote / #LI-Hybrid / #LI-Onsite 

EEO/AA 

US Benefits Overview

Canada Benefits Overview

UK Benefits Overview

If you like wild growth and working with happy, enthusiastic over-achievers, you'll enjoy your career with us!