Account Executive

Job Description

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.

Key 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

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

Desired Skills & Attributes:

• 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

Why Join Pinewood.AI?

Pinewood.AI is a global automotive technology company using data and AI to help dealers operate better, sell more, and deliver stronger customer experiences. Our platform supports sales, service, and dealership operations while working alongside existing systems.

With the recent acquisition of Seez, a leader in AI-powered automotive retail solutions, Pinewood.AI is scaling quickly. Seez’s proven AI technology and international success, combined with Pinewood.AI’s deep industry footprint, are fueling our expansion in the U.S., including a strategic partnership with Lithia Group, one of North America’s largest dealership networks.

We’re building a team to shape the future of automotive retail and are looking for people who want to make a real impact as we grow.

About Us

Our story began more than 20 years ago with a clear purpose to create technology designed around the real needs of automotive retailers. As automotive professionals as well as technologists, we built practical solutions that help dealerships run more efficiently and deliver outstanding customer experiences. 

Today, Pinewood.AI is a market leader in dealership management and automotive intelligence. Our cloud-based platform connects every part of a retailer’s business, including vehicle sales, service, parts, workshop, finance, insurance, stock management, customer relationship management, and business reporting. By bringing everything together in one intelligent system, we help retailers and manufacturers make better decisions, improve performance, and increase profitability. 

We are now expanding into North America, bringing our proven platform to a new audience. This is an important stage in our growth where we are building our presence in the United States and Canada. Joining Pinewood.AI at this time means becoming part of a fast-growing, startup-style team that is supported by an established and successful global business. You will play a key role in introducing and embedding our platform across North American dealerships. 

Benefits

• A very competitive salary plus commission structure
• Flexible mix of home and office working 
• Clear path for career advancement as our US sales organization grows

• 4 weeks PTO 

• 401k 
• Excellent health insurance benefits

• Regular 1-2-1s and career development opportunities
• Opportunity to be part of an early-stage US sales team with real ownership