Director, Field Sales - MidSouth

About Cars Commerce

Cars Commerce simplifies everything about buying and selling cars, offering a broad portfolio of marketplace, dealership websites, trade, and media solutions. It is committed to collaboration, growth, and an inclusive culture.

The Group Director is a senior field sales leader responsible for driving revenue growth and commercial excellence across a multi‑territory region. It leads a team of approximately 15 Senior Account Executives and serves as the connective tissue between front‑line execution and strategic direction.

• Team Leadership and Talent Development
  • Lead, coach, and develop a team of ~15 Senior Account Executives across a defined multi‑state region
  • Conduct regular field rides, deal reviews, and one‑on‑one sessions to assess performance and accelerate skill development
  • Partner with HR and Talent Acquisition to recruit, onboard, and retain top‑tier field sales talent
  • Build a high‑performance team culture grounded in accountability, intellectual curiosity, financial hunger, and dealer‑first thinking
  • Identify and develop future leaders within the team; model the behaviors to be replicated at every level
• Revenue Ownership and Forecasting
  • Own regional revenue targets across the Cars Commerce portfolio (, Dealer Inspire, Accu‑Trade, and digital media solutions)
  • Maintain rigorous pipeline and forecasting discipline in Salesforce; roll up a reliable, evidence‑based forecast to the Field VP on a weekly and monthly cadence
  • Drive consistent attainment across the entire team through structured coaching and performance management
  • Identify revenue risk early and implement proactive mitigation strategies across the roster
• Strategic Territory and Account Oversight
  • Oversee territory design and account assignments to maximize market coverage and revenue potential across the region
  • Guide Senior Account Executives in developing and executing strategic account plans for large dealer groups and multi‑rooftop accounts
  • Engage directly with key regional dealer groups and high‑value accounts as an executive sponsor
  • Identify regional whitespace and growth opportunities and build go‑to‑market plans to capture them
• Cross‑Functional Partnership
  • Primary field liaison between the region and internal stakeholders (Customer Success, Dealer Success, Product, Marketing)
  • Partner with the Field VP and peer Group Directors to align on commercial strategy and drive consistency across the national organization
  • Surface field‑level market intelligence, competitive dynamics, and dealer sentiment to inform product roadmap and go‑to‑market decisions
• Operational Excellence
  • Enforce CRM hygiene, pipeline management standards, and forecasting accuracy across the team
  • Drive adoption of sales tools, processes, and playbooks; champion consistency in positioning and selling the Cars Commerce platform
  • Coach sellers to an agreed sales methodology and run deal reviews to identify stage
  • Travel regularly across the region for field visits, team accompaniment, dealer meetings, and strategic account calls

• 10+ years of B2B sales experience
• At least 5+ years in a field sales leadership role managing quota‑carrying individual contributors
• Demonstrated success leading teams that sell complex, multi‑product or platform solutions in a consultative sales motion
• Track record of meeting or exceeding team revenue targets in a high‑activity, field‑based environment
• Experience managing geographically dispersed teams across multiple territories
• Strong CRM discipline and ability to coach teams on pipeline data
• Automotive retail industry experience (dealerships, dealer groups, OEM channels, or automotive technology/media) strongly preferred

• SaaS, digital media, or marketing technology sales leadership, particularly in verticals with SMB‑to‑enterprise dealer or franchisee dynamics
• Experience overseeing sales to multi‑rooftop dealer groups or large regional/national franchise accounts
• Familiarity coaching sellers on automotive retail metrics and dealer P&L dynamics (VDP views, leads, inventory turn, digital retailing, trade funnels)
• Prior experience operating within a layered field sales organization (IC…