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Open nowPosted 180 days ago

AI-Native Founding Account Executive

Workable (global search)108,016 open roles

Where
Canada
Work mode
Remote
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Your applicationOpen nowAI-Native Founding Account ExecutiveWorkable (global search) · Canada

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The clock on this job

Early applications get read.

7.9% of postings close within 7 days. Measured by our own scanner across the market. Workable (global search) postings stay open a median of 7 days.

Share of postings closed within
  1. 1.6%1 day
  2. 3.6%3 days
  3. 7.9%7 days
  4. 14.9%14 days
  5. 34.0%30 days
This job: posted 180 days ago

Workable (global search) median: 7 days open

The posting

The Opportunity

We’ve built a new cloud-based SaaS product that solves a high-value problem in enterprise IT lifecycle management—and early traction through our existing customer base has validated product-market fit.

Now we need someone who can take that signal and turn it into a repeatable revenue engine. As our Founding AE, you’ll own the full sales cycle from first touch to closed-won, build pipeline from scratch, and help define the commercial playbook that scales the business.

You’ll be backed by permanent capital, built-in distribution through an established customer base in regulated markets (higher ed, public sector, healthcare), and a product with a clear platform expansion path. This is a ground-floor opportunity with a direct line to sales leadership as the business grows.

What You’ll Do

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

What We’re Looking For

Must-Haves

  • 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

Nice-to-Haves

  • 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)

Compensation

Base salary + commission (OTE) tied to revenue outcomes, with a ramp period and milestone-based accelerators aligned to early-stage growth. Remote-friendly with travel for key customer meetings and conferences.

If you sell with conviction, build with AI, and want to own the commercial trajectory of a product with real market pull—we want to hear from you.

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