Aspire Software

AI Sales Representative

Aspire Software

full-time

Posted on:

Location Type: Remote

Location: Remote • California, Florida, New York • 🇺🇸 United States

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Job Level

Mid-LevelSenior

About the role

  • · 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.

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.

Applicant Tracking System Keywords

Tip: use these terms in your resume and cover letter to boost ATS matches.

Hard skills
automotive software salesdigital retailing salestechnology solutions salesoutbound salespipeline managementdemo presentationcommunication solutionsCRM experienceAI-driven solutionssales cycle management
Soft skills
strong communication skillsself-managementcollaborationpresentation skillsnetworkingcustomer supportinsight generationproblem-solvingadaptabilitytime management