AI-Native Founding Account Executive
Company shown to members 🔒 · Remote · Canada only
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First recorded by Psst: 14 October 2026. Your first 3 jobs are free to apply to (the first right away, 2 more with your email). After that, the company and the apply link are for Psst members, from $4.99 for 7 days.
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The 20-second read
- Experience
- Senior
- Where you can live
- Canada only
- Skills and tools
- prospecting, b2b, saas, negotiation
Read from the ad by Psst's rules. Check the full ad below before applying.
Job details
- Where you can work
- Canada
- Employment type
- Not stated by the employer
- Advertised pay
- Not stated by the employer
- Experience
- Senior
- Employer publication date
- 7 April 2026
- First recorded by Psst
- 14 October 2026
- Last checked at the source
- 10 November 2026
About the job
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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- Open 7 months
- No pay listed
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