AI-Native Founding Account Executive in Winnipeg

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.

Description

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.