Aspire Software
We never stop building. A vertical acquisition software company that owns, operates and manages a diverse portfolio.
AI Sales Representative
Location
California + 2 moreAll locations: California, Florida, New York
Posted
104 days ago
Salary
Not specified
Bachelor Degree3 yrs expEnglish
Job Description
· Identify and target dealerships throughout the assigned region (West Coast, Northeast, or Florida).
· Run outbound sequences across phone, email, LinkedIn, and in-person visits.
· Use an existing automotive tech network to accelerate regional penetration.
· Build and manage a strong outbound-driven pipeline.
· Qualify inbound leads from dealerships within the assigned territory.
· Conduct discovery calls to understand dealership workflows and operational bottlenecks.
· Book and run demos, converting interest into qualified opportunities.
· Deliver compelling demonstrations of AI-powered communication solutions.
· Manage the full sales cycle including prospecting, discovery, demo, proposal, negotiation, and close.
· Support customers throughout early activation and hand off accounts to onboarding teams.
· Represent the company at automotive conferences, trade shows, and dealer-group events.
· Build regional brand presence and maintain visibility within key markets.
· Conduct in-person dealership visits for advanced demos or late-stage deal discussions.
· Collaborate with leadership, sales, and product teams.
· Provide regional insights into dealership needs, processes, and common DMS systems (e.g., CDK, Reynolds, Dealertrack, Tekion, XTime).
· Maintain accurate pipeline documentation and activity tracking in HubSpot.
· Provide consistent updates on territory progress and performance.
Job Requirements
- 3+ years of experience in automotive software or digital retailing sales.
- Experience selling technology solutions to dealerships within at least one target region.
- Background with companies such as Tekion, CDK Global, Reynolds & Reynolds, XTime, Dealertrack, Keyloop, AutoTrader/Cox, MotorK, or similar automotive SaaS vendors.
- Strong existing network in West Coast, Northeast, or Florida dealership groups.
- Proven success in a hunter-style role with consistent outbound activity.
- Strong demo, presentation, and communication skills.
- CRM experience, ideally HubSpot.
- Ability to self-manage in a fast-paced, remote startup environment.
- Comfort explaining AI-driven or technical solutions to non-technical dealership teams.
- Based in one of the eligible U.S. regions with ability to visit dealerships as needed.
Benefits
- Competitive base salary.
- Uncapped commission with strong earning potential.
- Fully remote role within the assigned U.S. region.
- Opportunity to be among the first regional U.S. sales hires.
- Training in AI, automotive workflows, and advanced sales methodologies.
- Fast-paced, ambitious environment with significant growth opportunity.
- Direct impact on expanding presence in the most innovative dealership markets.
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