Account Executive, Pinewood AI

• Success in this role requires a self-starter mindset, comfort leading executive-level sales cycles, and the ability to clearly position platform-level value across multiple solutions
• 5+ years of enterprise/B2B software/SaaS sales experience with automotive technology
• Demonstrated success meeting or exceeding quota in previous roles
• Experience with consultative selling and complex, multi-stakeholder sales processes
• Strong understanding of automotive dealership operations and technology landscape
• Excellent communication, presentation, and negotiation skills
• Ability to build and maintain relationships at multiple levels of an organization
• Bachelor's degree or equivalent experience required
• Willingness to travel up to 65% of time within assigned territory

Desirable

• The primary expectation is aggressive new logo acquisition across your assigned territory. You will prospect, engage, and close new dealer groups, positioning Pinewood.AI’s DMS and AI-powered solutions as mission-critical platforms for modern automotive retail
• This is a true hunter role focused on opening new relationships, creating demand, and closing complex enterprise deals with large dealership groups. This role is built for a self-starter who thrives in competitive sales cycles, navigates executive conversations with confidence, and owns outcomes
• You will own your territory end to end, building pipeline, leading executive conversations, and consistently closing new business across large dealer groups
• Hunt, prospect, and close new dealership groups for Pinewood.AI’s DMS and Seez’s AI-powered solutions
• Own the full enterprise sales cycle from outbound prospecting through contract execution
• Drive expansion and cross-sell opportunities within Lithia Group dealerships across both platforms
• Build and execute a territory plan focused on pipeline creation, new logo acquisition, and revenue growth
• Engage dealership principals, general managers, CIOs, and executive leadership in strategic, value-based conversations
• Lead product demonstrations and executive presentations across DMS and Seez solution sets
• Develop clear business cases, ROI models, and commercial proposals tied to dealership outcomes
• Consistently generate and manage a pipeline that supports aggressive growth targets
• Accurately forecast opportunities and maintain disciplined CRM hygiene
• Partner closely with implementation and customer success teams to ensure strong post-sale transitions
• Collect competitive intelligence and field feedback to inform product and go-to-market strategy
• Represent Pinewood.AI and Seez at industry events, dealer meetings, and conferences
• Collaborate with marketing on outbound campaigns and targeted account penetration