Principal Product Manager

As the Hagerty Drivers Club Principal Product Manager, you will define the product vision, strategy, and roadmap that delivers innovation in features, usability, and performance, working directly with design, engineering, and business partners. You must be passionate about identifying consumer-facing problems and building impactful, data-driven solutions.

As a highly experienced B2C product leader, you will be the voice of the customer — translating member insights into digital experiences that deepen engagement, retention, and lifetime value.

This role requires a leader who moves fast, has an entrepreneurial spirit, possesses natural curiosity, sharp analytical skills, and can break down and solve complex problems. You’ll be expected to operate both strategically and tactically: thinking big to drive new opportunities, diving deep into the data to uncover customer insights, and working backward from the member to deliver measurable business impact.

If you know what's needed to make intricate products and teams successful — and can transform a vision with many pieces into an executable, iterative plan that delivers results — come join us.
 
Hagerty Drivers Club (HDC) is a membership program designed exclusively for classic and enthusiast car owners. The product is one of many that the Hagerty Customer Experience Technology (CXT) team creates. Our team is made up of motivated, customer-obsessed, forward-thinkers who view every interaction as an experience rather than a transaction.
 

The CXT team delivers end-to-end digital experiences across Hagerty’s ecosystem, including insurance quoting and management, Hagerty Marketplace, Drivers Club, and Media/Entertainment offerings. We design, build, and scale automotive experiences that connect people to the cars and culture they love. With a focus on strategy, design, user experience, and engineering, we create value at every touchpoint in the customer journey.

 Ready to get in the driver’s seat? Join us!

• Deliver consumer-facing product experiences that delight our members and demonstrate meaningful business impact on growth, engagement, and retention.
• Define success metrics, analyze data for insights, and prioritize initiatives that align with company strategy and measurable outcomes.
• Lead digital product development from ideation to launch, leveraging innovative technology – including personalization and marketing automation platforms – to create shippable products that deliver measurable value.
• Inform product strategy by gathering and analyzing customer feedback, monitoring competitors, and staying current with trends in subscription, loyalty, and membership programs
• Create structured strategy documents and product briefs that communicate customer needs, evaluate current state, and define a clear vision for future direction — breaking down execution into iterative releases with measurable results.
• Collaborate across design, engineering, marketing, and analytics to align priorities, dependencies, and decisions that drive member and business outcomes.
• Champion a test-and-learn culture, using experimentation and A/B testing to continuously improve product performance.
• Mobilize teams to do their best work by providing clear direction, managing dependencies, and removing roadblocks.

• Extensive experience in end-to-end B2C digital product management at large companies or high-growth startups, with a proven record of launching impactful digital products.
• Deep expertise in subscription or membership-based models (e.g., loyalty, rewards, digital communities, or paid experiences).
• Experience with marketing technology ecosystems, including personalization, CRM, digital communities, or paid experiences.
• Proven ability to define product vision and strategy, create data-driven roadmaps, and successfully bring consumer products to market.
• Strong proficiency in developing comprehensive product strategies and frameworks to prioritize initiatives and resolve trade-offs.
• Demonstrates technical fluency and analytical rigor — able to partner effectively with engineering, design, and data teams.
• Balances strategic and tactical execution; transforms ambiguity into clarity and action.
• Strong technical depth and systems mindset — comfortable engaging in technical discussions, understanding trade-offs, and connecting technical realities with member needs to guide practical, scalable, customer-focused decisions.
• Excellent communication skills — including strong written abilities — able to simplify complex topics, influence at all levels, and inspire cross-functional alignment.
• A systems thinker with exceptional attention to detail — able to connect how experiences, platforms, and processes interrelate to deliver cohesive member value.
• Strong owner mentality; thrives operating independently and collaboratively across multiple teams.

Other things to note

• This role can be worked from any U.S. remote location
• 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.

Say hello to Hagerty

Hagerty is an automotive enthusiast brand and the world’s largest membership organization. Along with being a best-in-class provider of specialty insurance for enthusiasts, Hagerty is also home to the Hagerty Drivers Foundation, Hagerty Drivers Club, Marketplace and so much more. Committed to saving driving for future generations, each and every thing Hagerty does is dedicated to the love of the automobile.

Hagerty is a rapidly growing company that values a winning culture. We provide meaningful work for and invest in every single team member.

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.

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. 

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