Sales Director

About Dealerware:

Dealerware transforms the automotive retailers of today into the mobility network of tomorrow. Launched in 2016, Dealerware manages tens of thousands of vehicles at dealerships in North America across every major manufacturer brand. Dealerware is committed to being a people-first culture and a great place to work for all, with flexible scheduling, unlimited PTO, extensive benefits, a core value of Diversity, Equity & Inclusion, and a leadership and management team that defaults to being supportive and accessible. Dealerware was recognized by Built In as one of the 100 Best Places to Work in Austin, TX in 2025 for the fourth consecutive year.

Dealerware is looking for a high-impact Sales Director to drive new business acquisition and revenue growth. In this role, you will own the entire sales cycle, from prospecting and lead generation to closing deals and expanding revenue. You’ll develop and execute strategic sales plans, build strong dealership and dealer group relationships, and leverage MEDDIC methodology to qualify and convert leads.

You’ll also work closely with internal teams—including Marketing, Customer Experience, and Product—to refine regional growth strategies and enhance Dealerware’s value proposition in the automotive space.

Job responsibilities:

• Drive new business growth by acquiring new dealerships and dealer groups, expanding revenue and achieving sales targets.
• Develop and execute territory sales plans to identify and convert high-potential prospects.
• Leverage the MEDDIC sales methodology to qualify leads, structure deals, and close business efficiently.
• Conduct compelling product demonstrations that showcase Dealerware’s impact on dealership operations and profitability.
• Build long-term, trusted relationships with key decision-makers at dealerships, dealer groups, and OEMs.
• Oversee contract negotiations to align on pricing, terms, and long-term success metrics.
• Collaborate with internal teams to refine regional sales strategies and drive product adoption.
• Maintain accurate pipeline tracking, sales forecasting, and CRM data management in Salesforce.
• Serve as the voice of the customer, providing valuable feedback to influence product development and company strategy.

Required qualifications:

• 5-7 years of outside sales experience selling complex solutions to automotive dealerships or OEMs/dealer groups.
• Proven track record of exceeding B2B sales quotas and closing high-value deals.
• Extensive dealership contacts and strong relationships within the automotive industry.
• Ability to travel up to 50%, including overnight travel.
• Expertise in consultative, solution-based selling that aligns a client’s business needs with a tailored solution.
• Strong experience in pipeline development, sales strategy, and revenue forecasting.
• Experience managing sales processes in Salesforce CRM and/or Outreach.

Preferred (Highly Desirable):

• SaaS experience in automotive, mobility, or fleet management.
• Experience selling subscription-based technology solutions to dealerships.
• Deep knowledge of automotive retail operations and dealership profitability models.

Dealerware offers you:

• Competitive base salary of $100,000–$120,000 a year with bonus incentive eligibility and commission
• Full benefits (medical, dental, vision, 401K)
• Opportunity to gain experience with a business that is headed in an upwards projection and constantly expanding in its space
• A company whose goal is for its employees, partners, and customers to feel they can show up fully and authentically in the shared communities, in and out of the workplace
• Tuition reimbursement, company-paid conference attendance and certifications
• Access to a wide array of free educational courses via an on-demand learning platform to foster a culture of growth and development

Dealerware is an Equal Opportunity Employer that does not discriminate on the basis of actual or perceived race, color, creed, religion, national origin, ancestry, citizenship status, age, sex or gender (including pregnancy, childbirth and pregnancy-related conditions), gender identity or expression (including transgender status), sexual orientation, marital status, military service and veteran status, physical or mental disability, genetic information, or any other characteristic protected by applicable federal, state or local laws and ordinances. Dealerware's management team is dedicated to this policy with respect to recruitment, hiring, placement, promotion, transfer, training, compensation, benefits, employee activities, access to facilities and programs and general treatment during employment.

*We are interested in every qualified candidate who is eligible to work in the United States. However, we are not able to sponsor visas.