Aspire Software

We never stop building. A vertical acquisition software company that owns, operates and manages a diverse portfolio.

AI Sales Representative

Account ExecutiveSalesFull TimeRemoteTeam 1,001-5,000H1B No SponsorCompany SiteLinkedIn

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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