Vice President of Sales

Accountabilities

Sales Strategy and Revenue Growth: Lead the direct sales organization and take ownership of new business revenue and bookings targets. Develop and implement sales strategies for individual dealerships, small and mid-sized dealer groups, and large multi-location organizations.
Sales Performance Management: Establish sales goals, territories, quotas, and performance expectations. Build a consistent and scalable sales process that improves productivity, conversion rates, deal size, and overall sales effectiveness.
Strategic Account Development: Personally engage in high-value sales opportunities, support complex negotiations, and help close significant transactions. Identify opportunities to expand existing customer relationships through additional products and services.
Team Leadership and Development: Lead, coach, recruit, and retain a high-performing inside sales team. Establish effective onboarding, training, and professional development programs while fostering a culture of accountability, collaboration, and continuous improvement.
Sales Operations and Forecasting: Maintain accurate sales forecasts and provide regular performance updates to executive leadership. Drive consistent use of Salesforce or comparable CRM platforms for pipeline management, forecasting, and reporting.
Metrics and Process Optimization: Define and monitor key performance indicators, including pipeline generation, conversion rates, sales productivity, and quota attainment. Identify opportunities to shorten sales cycles, improve execution, and increase average contract value.
Cross-Functional Collaboration: Partner with Marketing to strengthen lead generation, Customer Success to support retention and expansion, and Revenue Operations and Finance to coordinate sales planning, territories, quotas, and incentive compensation.
Product and Market Alignment: Collaborate with Product and Operations teams to share market insights, improve service delivery, and align solutions with dealership needs. Work with manufacturer-facing teams to capitalize on strategic programs and industry relationships.
Industry Representation: Represent the organization at automotive industry events, dealer group meetings, and strategic customer engagements. Build relationships with key decision-makers and identify emerging business opportunities.
Organizational Scaling: Develop the processes, tools, resources, and leadership structure needed to support sustainable growth. Ensure alignment across departments and establish a disciplined sales organization capable of delivering predictable results.
Requirements
Extensive Automotive Sales Experience: Significant experience selling automotive technology products or services directly to franchised dealerships, including individual dealership locations and large dealer groups. Direct dealership sales experience is mandatory.
Sales Leadership: Proven success leading and developing sales organizations serving the automotive dealership market, including inside sales teams and high-volume sales operations.
Automotive Industry Expertise: Strong understanding of automotive retail operations, dealership economics, and purchasing processes involving dealer principals, general managers, fixed operations leaders, and dealer group executives.
Technology and Recurring-Revenue Sales: Experience selling SaaS products, recurring-revenue technology solutions, or technology-enabled services directly to dealerships.
Complex Sales Management: Demonstrated ability to manage both transactional sales to individual dealerships and complex, multi-stakeholder opportunities involving large dealer groups.
Revenue Growth and Forecasting: Strong expertise in sales strategy, pipeline management, forecasting, territory planning, performance measurement, and quota attainment.
Team Building and Coaching: Proven ability to recruit, develop, motivate, and retain successful sales professionals while building a culture of accountability and achievement.
CRM and Sales Tools: Proficiency with Salesforce or a comparable CRM platform, along with the ability to use sales metrics and reporting tools to guide decisions and improve performance.
Communication and Relationship Management: Excellent leadership, negotiation, presentation, communication, and relationship-building skills, with the ability to influence stakeholders at all organizational levels.
Strategic and Analytical Thinking: Strong business acumen, sound judgment, and the ability to translate market insights into actionable growth strategies.
Preferred Industry Experience: Familiarity with automotive AI, dealership CRM platforms, business development center (BDC) services, lead management, customer engagement solutions, or related technologies.
Established Industry Network: Existing relationships with dealer groups and influential decision-makers across the automotive retail sector are highly desirable.
Growth-Stage Experience: Experience scaling sales organizations in private equity-backed or high-growth businesses is an advantage.
Sales Methodologies: Familiarity with structured sales methodologies, sales enablement programs, and repeatable commercial processes is preferred.
Location and Travel: Must be based in the United States, with candidates in the Eastern or Central time zones preferred. Ability to travel approximately 25% for company visits, dealership meetings, dealer group engagements, and industry events is required.
Important qualification note: This position requires an established automotive dealership sales leader. Experience limited to selling directly to automotive manufacturers (OEMs), or general B2B or SaaS sales experience without direct dealership sales experience, does not meet the core requirements.
Benefits
Competitive base salary: $200,000–$240,000 annually.
High earning potential: On-target total cash compensation of $375,000–$450,000 per year.
Uncapped commissions: Performance-based incentive compensation with accelerators for exceeding sales targets.
Equity participation: Eligibility to participate in the management equity incentive plan.
Healthcare coverage: Health benefits to support employee well-being.
Paid time off: Time away from work to support work-life balance.
Remote work arrangement: Work remotely from anywhere in the United States, with a preference for Eastern or Central time zones.
Executive leadership exposure: Report directly to the CEO and contribute to strategic decisions as a member of the executive leadership team.
Career and business impact: Lead an established sales team, shape commercial strategy, and contribute directly to the growth of an expanding automotive technology and services business.
Industry engagement: Opportunities to build strategic relationships with dealerships, dealer groups, and automotive industry partners.
Travel opportunities: Engage directly with customers and colleagues through visits to company offices in Monroe, North Carolina, and Boca Raton, Florida, as well as dealership locations and industry events. Approximately 25% travel is expected.