Director of Product & Project Management

About DealerOn We are an online marketing company providing website and agency services to automotive dealerships across North and South America. We are known for our cutting-edge products that streamline the car buying process and provide an experience both shoppers and dealers love. Our business model is working: we were recognized on the Inc. 5000 list of fastest growing companies six years in a row, expanding to over 30 manufacturer relationship, and over 5,000 dealer partners. We are proud of what our company has done, and it’s all due to the talented and diverse team we’ve been lucky enough to assemble. The Role DealerOn is seeking an experienced Director of Product Management to lead our content management ecosystem, including page building, content editing workflows, OEM integrations, internal performance tooling, Listings Manager, and Design Studio. This role combines strategic product leadership with hands-on product execution, driving the roadmap and evolution of core platform capabilities that power dealer websites and digital merchandising experiences at scale. You will partner closely with engineering leadership, design, operations, customer-facing teams, and executive stakeholders to shape the future of DealerOn’s CMS platform and dealer tooling. This role requires strong technical fluency, operational rigor, customer empathy, and the ability to balance long-term platform modernization with near-term customer needs. This role is well suited for an individual with experience leading complex product initiatives, influencing cross-functional stakeholders, and managing product team members in a fast-paced environment. Key Responsibilities CMS Platform & Dealer Tools Lead product strategy and roadmap development for DealerOn’s content management system (CMS). Drive the evolution of page building and content editing workflows for dealership and internal users. Oversee enhancements supporting Listings Manager and Design Studio products. Partner with OEM Business Development team to ensure scalable, compliant, and timely Improve dealer usability, operational efficiency, platform reliability, and timely execution of requests. Strategic Product Leadership Own end-to-end product strategy from discovery through launch, adoption, and optimization. Define long-term platform vision aligned with company objectives and customer needs. Identify and prioritize new product opportunities through customer feedback, market insights, and operational analysis. Balance platform modernization initiatives with tactical delivery priorities and customer commitments. Drive cross-functional alignment across engineering, design, operations, sales, customer success, and executive stakeholders. Define and monitor product success metrics including adoption, engagement, retention, conversion, operational impact, and revenue contribution. Tactical Product Management Serve as a hands-on product leader for critical platform initiatives and tactical execution teams. Write detailed product requirements, user stories, and acceptance criteria. Conduct customer interviews, workflow analysis, and usability testing to identify improvement opportunities. Translate complex technical systems and platform capabilities into intuitive dealer-facing experiences. Partner closely with engineering on architectural tradeoffs, technical feasibility, and implementation planning. AI-Assisted Product Development Leverage AI-assisted tools and emerging technologies to accelerate product discovery, documentation, prototyping, workflow analysis, and delivery efficiency. Utilize AI-enabled prototyping and workflow tools to rapidly validate concepts, user experiences, and operational improvements. Evaluate opportunities to incorporate AI and automation capabilities into DealerOn products and internal workflows where appropriate. Team Leadership & Development Build and mentor high-performing product management talent as organizational needs evolve. Coach product managers on product discovery, execution discipline, stakeholder management, and customer-centric thinking. Foster a culture of innovation, accountability, collaboration, and operational excellence. Influence organizational product processes and best practices. Cross-Functional Collaboration Lead cross-functional collaboration across Product, Engineering, UX, Marketing, Sales, Customer Success, Support, and Operations teams. Collaborate with business stakeholders to align platform investments with strategic business goals. Coordinate with external partners and OEM stakeholders on product initiatives. Support product launches through validation, stakeholder communication, enablement activities, and post-release analysis. Required Qualifications Bachelor’s degree or equivalent professional experience in Business, Technology, Marketing, Engineering, Computer Science, or a related field. 10+ years of product management experience, including significant experience leading platform or SaaS products. 5+ years of experience in senior product leadership roles with ownership of major product areas or platforms. Strong experience with CMS platforms, workflow systems, website publishing tools, or enterprise SaaS products. Proven track record of defining product strategy while maintaining strong execution involvement. Excellent technical fluency and ability to contribute meaningfully in architecture and platform discussions. Experience partnering closely with engineering teams on APIs, integrations, platform scalability, and system design. Strong written and verbal communication skills across customers, executives, and technical stakeholders. Demonstrated ability to influence cross-functional teams and drive organizational alignment. Customer-centric mindset with strong product judgment and bias toward execution. Proficiency with modern product management and collaboration tools such as Jira, Confluence, Productboard, Aha!, Miro, Figma, or similar platforms. Ability to manage ambiguity, balance competing priorities, and lead initiatives independently in fast-paced environments. Preferred Qualifications Experience in automotive retail, dealership technology, or adjacent vertical SaaS industries. Experience with OEM integrations or compliance-heavy product environments. Background working on multi-tenant SaaS platforms or enterprise workflow systems. Experience with website builders, design systems, digital merchandising, or content publishing tools. Track record of product leadership in high-growth technology organizations. Experience with analytics platforms such as GA4 and Pendo. Experience leveraging AI-assisted tools such as ChatGPT, Claude, Lovable, v0, Figma AI, or similar technologies. Experience building prototypes, workflows, or concept validations using Figma, Miro, Balsamiq, or AI-enabled prototyping tools. Why DealerOn You’ll help shape the future of the platform powering thousands of dealership websites and digital retail experiences. This is an opportunity to lead highly visible products that directly impact dealer operations, merchandising, customer engagement, and website performance at scale. You’ll work alongside talented teams across product, engineering, and design while influencing the evolution of DealerOn’s next-generation website platform. What We Offer Competitive base salary and bonus compensation Comprehensive benefits package including health, dental, and vision insurance Flexible work arrangements and professional development opportunities Opportunity to shape strategic platform investments at a rapidly growing company Collaborative culture with access to cutting-edge technology and resources Direct impact on product strategy, platform innovation, and customer experience Reporting Structure This role reports directly to the VP of Product and is a member of the senior product leadership team. The position includes responsibility for cross-functional product leadership, strategic roadmap ownership, and mentorship of product management talent across key platform initiatives. #LI-Remote This position is open to US residents only. The targeted salary range for this position is $106,400 - $161,400. The posted salary range for this position may be adjusted based on job-related factors permitted by law, such as experience and training; internal pay equity; licensure and certifications; market factors; departmental budgets; and responsibility. Our Talent Acquisition Team will be happy to answer any questions. Perks and Benefits: Aside from the awesome people you will get to interact with on a daily basis, we offer a number of benefits, including: Medical, dental and vision insurance Company matched 401K plan Flexible PTO + Sick Leave 6 weeks paid Parental Leave 8 Paid National Holidays Company-paid basic Life Insurance Voluntary supplemental Life Insurance Voluntary long-term/short-term disability insurance Voluntary Pet Insurance Optional Healthcare/Dependent Care FSA Account DealerOn is an Equal Opportunity Employer. We celebrate diversity and are committed to creating an inclusive environment for all employees. We also participate in E-Verify (for more information, click here: E-Verify Participation and Right to Work ). A successful candidate must pass a background check as a condition of joining the team.