Director, Field Sales - MidSouth

About the role

The Group Director is a senior field sales leader responsible for driving revenue growth and commercial excellence across a multi-territory region. In this role, you will lead a team of approximately 15 Senior Account Executives—seasoned, consultative sellers operating across geographically distributed dealer territories—and serve as the connective tissue between front-line field execution and the strategic direction set by the Field VP.

Responsibilities

• 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-ones to assess performance, reinforce consultative selling behaviors, and accelerate skill development
  • Partner with HR and Talent Acquisition to recruit, onboard, and retain top-tier field sales talent—screening for the full DRIVE profile at every hire
  • 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 you want replicated at every level below you

• Revenue Ownership and Forecasting

  • Own regional revenue targets across the full Cars Commerce portfolio: Cars.com marketplace, Dealer Inspire, Accu-Trade, and digital media solutions
  • Maintain rigorous regional 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—not just top performers—through structured coaching and performance management
  • Identify revenue risk early and implement proactive mitigation strategies across your Senior Account Executives roster

• Strategic Territory and Account Oversight

  • Oversee territory design and account assignments to maximize market coverage and revenue potential across your 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, reinforcing Cars Commerce's platform value at the most senior levels
  • Identify regional whitespace and growth opportunities and build go-to-market plans to capture them

• Cross-Functional Partnership

  • Serve as the primary field liaison between your region and internal stakeholders—including Customer Success, Dealer Success, Product, and Marketing—to ensure seamless dealer experiences and feedback loops
  • Partner with the Field VP and peer Group Directors to share best practices, align on commercial strategy, and drive consistency across the national field 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—the standard starts with you
  • Drive adoption of sales tools, processes, and playbooks; champion consistency in how the Cars Commerce platform is positioned and sold
  • Operate within and coach to a named sales methodology; be able to run a deal review and identify where a seller is in the process

Requirements

• 10+ years of B2B sales experience, Must have 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 the ability to read, coach from, and hold teams accountable to pipeline data
• Automotive retail industry experience (dealerships, dealer groups, OEM channels, or automotive technology/media) strongly preferred

Preferred Experience

• 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 → Manager → Director → VP structure)

Skills and Competencies

• Executive presence with the ability to engage credibly at the dealer principal, GM, and C-suite level—and to model that presence for your team
• Strong coaching instincts; elevates sellers by asking great questions, not just providing answers
• Analytical and operationally rigorous; comfortable managing a large pipeline and translating data into actionable coaching and strategy
• Unapologetically money-motivated—energized by the earning potential of this role and able to recruit and inspire the same drive in others
• Ability to hold the team accountable without sacrificing culture or morale
• High travel tolerance; this is a field-intensive leadership role with regular regional travel expected
• Proficiency with Salesforce and virtual presentation/collaboration platforms