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DealerPolicy Senior Product Director, Automotive in Boston, Massachusetts

We’re tripling our Product Development Team. To prepare for this explosive growth, we are seeking a dynamic innovator to lead our Automotive vertical as the Senior Product Director.

At DealerPolicy, we're changing the way people shop for insurance through technology. We’ve teamed with top auto retailers in the country to deliver a unique point of sale, technology enabled insurance solution to car-buying customers. Our efforts have earned us the Liberty Mutual “Agent of the Future” and Travelers “Agent of the Year” awards and best Tech Startup in VT from the Tech Tribune. Poised to expand rapidly, we need the right auto retail expert to help take our product team to the next level.

What Success Looks Like

  • Create, socialize, and manage the annual plan for DealerPolicy’s distribution dominance in the automotive space

  • Deliver auto insurance quotes to every car-buying customer in DealerPolicy dealerships

  • Establish DealerPolicy’s presence throughout the digital car buying experience

  • Design, launch and manage dealer reward and incentive programs that drive product usage

  • Ensure the continued success of our partnership dealer acquisition model

Roles and Responsibilities

  • Work with DealerPolicy’s executive leadership team to execute against our strategic plan and deliver innovation to market

  • Lead the Automotive vertical roadmap planning, management, and execution

  • Partner with Human Resources to build a world-class Team of Product Managers focused on delivering and managing customer-centric solutions in the Automotive Market

  • Collaborate with Design/UX and Engineering to ensure efficient and timely delivery of elegantly created products to our customers

  • Engage stakeholders throughout DealerPolicy including Marketing, Business Development, Operations, and Dealer Operations to ensure the success of new products and features in the market

  • Coach and motivate the Automotive Product Team to drive business results and advance their professional development

  • Manage product performance by pulling together customer research and quantitative data to inform feature iterations


  • 5+ years’ experience in product development, 2+ years in a leadership role in an agile environment

  • 5+ years’ experience working in automotive dealerships, OEM’s, F&I agencies, or software providers, preferred to overlap with above

  • Deep, detailed understanding of the automotive industry, its key players and their motivations including dealers, dealer personnel, OEMs, software providers, and marketers

  • Exceptional verbal and written communication and presentation skills; ability to influence and persuade across all levels of an organization

  • A demonstrated customer-focused mindset and philosophy that actively engages users for input and puts them at the center of every design decision

  • Intimate understanding of motivational and persuasive design in both theory and practice

  • Proven track record of innovation in the product space

  • Strong quantitative and process-based analytical skills and the ability to understand and model complex business environments to drive real results

  • Extraordinary organizational skills


DealerPolicy offers a comprehensive Benefits Package, which includes

  • Medical, Dental and Vision Insurance

  • Health Savings Account with company match

  • FSA, Dependent Care FSA and Commuter pre-tax benefit

  • PTO allowance and holidays

  • 401(k) plan with company match

  • Working remotely or Hybrid

  • Paid Volunteer Hours

About DealerPolicy

DealerPolicy is the most trusted and complete digital insurance marketplace for automotive retailers and their valued customers. The company’s innovative mobile technology enables car-buyers to view multiple insurance quotes and immediately connect with licensed insurance agents to purchase insurance. With an exclusive combination of partnerships among premier automotive retailers and data providers, an industry-best insurance carrier network, and access to DealerPolicy Insurance licensed agents, DealerPolicy is recognized for its place at the forefront of Insurtech. DealerPolicy Insurance is a licensed insurance agency, with licenses to operate in the lower 48 states. For more information, visit