Aspire Software

Founding Account Executive, AI-Native

Aspire Software

full-time

Posted on:

Location Type: Remote

Location: Canada

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Tech Stack

ITSM

About the role

  • Own the Full Sales Cycle
  • Run end-to-end deal execution: prospecting, discovery, demo, proposal, negotiation, and close
  • Build pipeline through targeted outbound, events, partnerships, and personal network leverage
  • Navigate complex buying committees (IT, procurement, finance) in enterprise and public-sector organizations
  • Land net-new logos across higher ed, healthcare, and adjacent verticals
  • Sell with AI as Your Unfair Advantage
  • Use AI tools, agents, and automation to drive outbound volume that would normally require a full SDR team
  • Build AI-powered workflows for prospecting, personalization, call prep, and follow-up sequencing
  • Leverage AI to analyze customer conversations, extract buying signals, and surface patterns that sharpen your approach
  • Treat your GTM stack like a product—always experimenting, always iterating
  • Help Build the Playbook
  • Refine ICP, positioning, and talk tracks based on what actually converts in-market
  • Capture buyer feedback and partner with product/engineering to shape the roadmap
  • Document what works so the next hires can ramp faster—you’re laying the foundation for a team
  • What Success Looks Like
  • First 30 days: Deep product fluency, target account list built, outbound motion live and producing conversations
  • 60–90 days: Qualified pipeline with measurable conversion, early wins in motion, AI workflows accelerating velocity
  • 6–12 months: Consistent closed-won revenue, multiple reference customers, and a clear case for expanding the sales team

Requirements

  • 4–10+ years in B2B SaaS sales with full-cycle closing experience
  • Proven ability to create pipeline and close deals—you manufacture demand, not just manage inbound
  • Experience selling into complex organizations with multiple stakeholders and procurement processes
  • Active, demonstrated use of AI tools in your sales workflow—not aspirational, real
  • Builder mindset: high ownership, structured execution, comfort in ambiguity
  • Experience in higher ed, public sector, healthcare, or other regulated environments
  • Familiarity with ITSM, ITAM, SAM, or procurement/vendor management concepts
  • Experience launching a new product or building a GTM motion from scratch
  • Partner or channel experience (associations, consultants, resellers)
Applicant Tracking System Keywords

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

Hard Skills & Tools
B2B SaaS salesfull-cycle closingpipeline creationdeal closingAI toolsproduct launchGTM motionsales workflowoutbound salescustomer conversation analysis
Soft Skills
builder mindsethigh ownershipstructured executioncomfort in ambiguitycollaborationfeedback captureexperimentationiterationcommunicationnegotiation