Director, Field Sales - MidSouth

Be essential at Cars Commerce At Cars Commerce, we’re fanatical about simplifying everything about car buying and selling. We do right by our customers and consumers to better connect the industry with simplified and tierless technology to enhance, measure and drive local automotive retail. Whether through our No.1 most recognized marketplace, Cars.com, our industry-leading digital experience, Dealer Inspire, our trade and appraisal technology, AccuTrade, our reputation-based digital wholesale auction marketplace, Dealerclub, or our new Cars Commerce Media Network, Cars Commerce is essential for success in the automotive industry. No one ever travels alone here: at its core, Cars Commerce is collaboration. In fact, it’s built into the very fabric of our shared values. We like to say we Rise Together – putting people at the center of what we do, from consumer to customer to community. Life at Cars Commerce makes it easy when we share the ethos to be Open to All, encouraging open-minded communication because we know diverse thinking yields better outcomes. But critical to our success is Caring to Challenge and Taking Ownership, fueling a competitive spirit in a respectful environment where we think about tomorrow but act today. At our foundation, we have integrity, Doing the Right Thing, even when it’s hard. It’s our shared commitment to these values that makes Cars Commerce a place where growth becomes not only possible, but downright unavoidable. But don't take our word for it. We are proud to be named one of Built In's 2026 Best Places to Work in Chicago and across the U.S. Ready to make your mark? Join a team that's driving real change in the automotive industry. 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. Senior Account Executives, Account Executives, Account Managers, and Client Partners (media and website sales specialists) all report up through this role. The Group Director is accountable not just for the output of the team, but for the standard of talent, culture, and execution that defines it. This is a player-coach leadership role for someone who thrives in a high-complexity, high-accountability environment. You know how to develop elite sellers, manage a large and dynamic pipeline, and build the kind of team culture that wins consistently. You bring deep automotive or vertical SaaS experience, strong executive presence, and the operational rigor to run a scaled field organization without losing sight of the individual dealer relationships that drive growth. WHAT YOU'LL DO: 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 Travel regularly across your region for field visits, team accompaniments, dealer meetings, and strategic account calls WHAT WE'RE LOOKING FOR: Required Experience 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 WHY THIS ROLE, WHY NOW, WHY CARS? Cars Commerce has the broadest product portfolio in its history — marketplace, websites, trade, and media — and is restructuring its commercial organization to sell that portfolio as an integrated platform with real dealer ROI at its center. The Group Director is the engine that makes that transformation real at scale. If you are a proven field sales leader energized by building great teams, driving meaningful revenue, and operating at the intersection of strategy and execution, this is your moment. In this spirit of pay transparency, we are excited to share the compensation for this role. The range is expressed as total target compensation (base salary + variable). If you are hired at Cars Commerce, your total target compensation will be determined based on factors such as skills and/or experience. If the range is close to what you're seeking, then we encourage you to apply and learn more about the total compensation package and benefits for this position. Total Target Compensation Range $228,600.00-285,750.00 Our Comprehensive Benefits Package includes: Medical, Dental & Vision Healthcare Plans New Hire Stipend for Home Office Set-Up Generous PTO Paid Holidays, Floating Holiday, Volunteer Day, Recharge Day Learn more about our Benefits, Perks, & Culture on our LinkedIn Life Pages! For US-based Positions: Applicants must be authorized to work in the United States. Please note that we are unable to sponsor employment visas at this time. We are an equal opportunity employer and value diversity at our company. We do not discriminate on the basis of race, religion, color, national origin, gender, sexual orientation, age, marital status, veteran status, or disability status. Applicants: Click here to review our Privacy Policy for Applicants. For current employees, please click here to review our California Privacy Policy for Employees. Welcome! At Cars Commerce, we think big, push boundaries, and rise together as a team. It’s all the challenge and energy of a job in the tech industry, backed by 25 years of proven resilience and growth as a leading consumer brand. Imagine getting to work on a team with a bold mission to simplify everything about buying and selling cars. A culture that’s a unique mix of innovation and collaboration. Exciting training and development opportunities that empower you to take ownership of your career. For our employees, every day is an opportunity. We’re a remote-first workplace that embraces diversity at every level. Inspired by our values, we intentionally create opportunities for our employees to grow and make an impact in our industry and local communities. Let’s move your career forward together. Cars Commerce is an audience-driven technology company empowering automotive that simplifies everything about buying and selling cars. The Cars Commerce platform includes the flagship automotive marketplace and dealer reputation site Cars.com, innovative digital marketing technology and services from Dealer Inspire, industry-leading trade-in and appraisal technology from AccuTrade, an exclusive in-market media network, and powerful and predictive AI technologies that enable more efficient and profitable retail operations. Cars Commerce is the essential partner to stay one step ahead in automotive.