AI-Native Founding Account Executive

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.

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

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.

Where you can sell from

Fully remote, for people based in Canada.