Major Accounts Sales Director
Job OverviewMajor Accounts Sales Director THE ROLE This is a senior-level, quota-carrying role focused on acquiring and expanding relationships with established, multi-rooftop and enterprise dealer groups in a virtual setting. You'll own the full sales cycle from outbound prospecting through close on complex, strategic accounts. You know how to navigate group-level decisions, champion a value proposition across stakeholders, and drive durable, long-term partnerships.
You'll work closely with the VP of Sales and our Sales Executive team to build pipeline, close meaningful deals, and set the standard for what great looks like on our sales team.
WHAT YOU'LL DO - Dealer Acquisition & Pipeline Development
- Own an account territory of mid-market to enterprise dealership groups (multi-rooftop & regional automotive retailers), driving net-new partnerships from first contact through active performance.
- Build and manage a healthy, self-sourced pipeline through strategic outbound prospecting primarily over the phone, industry networking, trade events, and referrals.
- Develop and execute account plans for priority groups, mapping stakeholders from F&I Directors and GMs to Dealer Principals and group-level leadership.
- Lead compelling discovery conversations and presentations that connect Polly's embedded insurance marketplace to each dealership's revenue and customer experience goals.
- Navigate complex, multi-stakeholder sales cycles with a consultative approach, managing objections and building consensus across operational, financial, and executive decision-makers.
- Serve as a trusted advisor and primary point of contact for your accounts through the full acquisition journey, ensuring a seamless handoff to Dealer Success post-close.
- Leverage existing automotive industry relationships to accelerate introductions and build credibility at the group level.
- Stay deeply current on the competitive landscape, dealership group consolidation trends, and F&I ecosystem dynamics to position Polly effectively.
Team & Go-to-Market Contribution - Partner with the team to refine target account lists, outreach messaging, and qualification criteria for enterprise dealer groups.
- Share deal learnings, competitive intelligence, and market feedback with the VP of Sales and cross-functional teams to continuously sharpen our go-to-market strategy.
- Maintain rigorous CRM hygiene in Salesforce, forecasting accurately and keeping leadership informed on pipeline health.
- Mentor peers and model Polly's values: accountability, transparency, and a bias for action.
WHAT WE'RE LOOKING FOR - 5-8+ years of B2B sales experience, with a strong track record closing complex deals in or around the automotive retail industry (dealership group sales, F&I product sales, DMS/technology sales, automotive SaaS, or similar).
- Track record of President's Club or top sales awards at previous companies
- Direct experience working with or selling to franchise and independent dealerships primarily over the phone - you understand how a dealership operates, who the real decision-makers are, and how F&I economics work.
- Demonstrated success selling into multi-rooftop dealer groups, regional dealer associations, or enterprise automotive accounts.
- A true hunter: you build your own pipeline, run disciplined outbound, and don't wait for leads to come to you.
- Polished executive presence and the ability to command a room with dealers and group-level leadership.
- Strong command of a value-based, consultative sales methodology (MEDDIC, Challenger, or equivalent).
- Proficiency with Salesforce and a data-driven approach to managing your pipeline and forecast.
- Comfortable operating in a fast-paced startup environment where priorities shift and resourcefulness is a competitive advantage.
- Insurance industry knowledge (auto, P&C) is a plus but not required.
WORK AND LIFE BALANCED, WE'RE HERE FOR YOU - Medical, dental and vision insurance
- HSA, FSA, Dependent Care FSA and Commuter pre-tax benefit
- Flextime PTO and generous holiday time
- Paid Parental leave + baby cash
- Matching 401(k) contributions
- Life & disability Insurance
- Work from anywhere options
Compensation is $150,000-$180,000 on target with no cap
