Account Executive

Pinewood.AI

18d•Hybrid

About The Position

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. 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.

Requirements

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

Nice To Haves

Established network in the US automotive dealership industry
Experience selling AI/ML or data analytics solutions
Knowledge of dealership management systems and digital retail technologies
Hunter mentality with ability to develop new business opportunities
Strategic thinking and creative problem-solving abilities
Data-driven approach to territory management and pipeline development
Self-motivated with ability to work independently in a remote capacity
Comfortable in a startup environment with evolving processes and priorities

Responsibilities

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