Job Overview
Location
US - Remote
Job Type
Full-time
Category
Software Engineering
Date Posted
June 6, 2026
Full Job Description
đź“‹ Description
- • Serve as a remote Major Accounts Sales Director responsible for acquiring and expanding partnerships with multi-rooftop and enterprise-level automotive dealership groups across the United States.
- • Own the full sales cycle—from outbound prospecting and lead generation to negotiation, closing, and handoff to the Dealer Success team—for high-value dealership accounts.
- • Build and manage a self-sourced pipeline through strategic phone-based outreach, industry networking, trade events, and referrals, with no reliance on inbound leads.
- • Develop and execute customized account plans for priority dealership groups, mapping key stakeholders including F&I Directors, General Managers, Dealer Principals, and group-level executives.
- • Conduct consultative discovery conversations and presentations that align Polly’s embedded automotive insurance marketplace with each dealership’s revenue goals, customer experience objectives, and F&I economics.
- • Navigate complex, multi-stakeholder sales cycles by building consensus across operational, financial, and executive decision-makers within large dealership organizations.
- • Leverage existing relationships within the automotive retail industry to accelerate introductions, establish credibility, and shorten sales cycles with enterprise dealer groups.
- • Stay deeply informed on competitive dynamics, dealership consolidation trends, and evolving F&I ecosystem developments to position Polly as the market leader in embedded auto insurance.
- • Partner with the VP of Sales and Sales Executive team to refine target account lists, improve outreach messaging, and enhance qualification criteria for enterprise dealership prospects.
- • Share real-time competitive intelligence, market feedback, and deal learnings with cross-functional teams to continuously optimize Polly’s go-to-market strategy.
- • Maintain rigorous Salesforce CRM hygiene, ensuring accurate forecasting, pipeline tracking, and leadership reporting on deal progress and health.
- • Mentor peers on the sales team by modeling Polly’s core values: accountability, transparency, and a bias for action.
- • Act as the primary trusted advisor and point of contact for enterprise dealership accounts throughout the entire acquisition journey, ensuring seamless transition to post-sale support.
- • Operate in a fast-paced startup environment where agility, resourcefulness, and adaptability are essential to driving growth and meeting evolving business priorities.
🎯 Requirements
- • 5–8+ years of B2B sales experience with a proven track record closing complex deals in the automotive retail industry (e.g., dealership group sales, F&I product sales, DMS/technology sales, automotive SaaS)
- • Demonstrated success selling to multi-rooftop dealer groups, regional dealer associations, or enterprise automotive accounts
- • Direct experience working with or selling to franchise and independent dealerships primarily over the phone, with deep understanding of dealership operations and F&I economics
- • Track record of achieving President’s Club or equivalent top sales awards at previous companies
- • Proven ability to build and manage a self-sourced pipeline using disciplined outbound prospecting
- • Proficiency with Salesforce and a data-driven approach to pipeline and forecast management
🏖️ Benefits
- • Medical, dental, and vision insurance
- • HSA, FSA, Dependent Care FSA, and Commuter pre-tax benefits
- • Flextime PTO and generous holiday time
- • Paid Parental leave + baby cash
- • Matching 401(k) contributions
- • Life & disability insurance
- • Work from anywhere options
Skills & Technologies
About Polly Insurance Agency, LLC
Polly Insurance Agency, LLC operates an embedded insurance marketplace, empowering car dealerships to seamlessly offer comprehensive insurance solutions to their customers at the point of sale. Their platform integrates directly into the sales process, allowing car buyers to instantly compare and purchase auto, home, life, and business insurance from over 40 trusted carriers. This innovative approach simplifies insurance acquisition, potentially saving customers significant amounts annually. Polly has demonstrated substantial scale and impact, having successfully insured $11 billion in cars and homes and generated over 5 million quotes, solidifying its position as a key partner for dealerships looking to enhance their customer offerings.
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