AI-Native Founding Account Executive

Valsoft Corporation · Remote · Canada

Base: Not disclosed
OTE: Not disclosed
Quota attainment: Not disclosed
Posted: 6mo ago

Why it matters: OTE tells you what you could earn. Attainment tells you how realistic it is.

Ask: “What percentage of fully ramped reps hit quota last year?”

Still open · checked 2h agoon Valsoft Corporation's careers page

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The job

What you'd do: Sell a cloud SaaS product for enterprise IT lifecycle management to higher ed, healthcare, and public-sector buyers. You own the full cycle, build pipeline from scratch via outbound and events, and work multi-stakeholder buying committees.
Who you'd sell to: Still reading the posting. Check back within the hour.
Where deals come from: Mostly you. Expect a lot of outbound: cold calls, emails and LinkedIn.

The Braun Read

Ask hard questions

Too much is left unsaid. Make them answer before you invest.

Pay: No pay listed at all.
Transparency: Says nothing about quota, attainment, deal size, territory or sales cycle.
Time on market: Open 208 days. Ask why it's been hard to fill.
Company hiring: 22 sales roles open, hiring at a steady pace.

Red lights

None spotted.

Yellow lights

Open 90+ days. This role has been posted for three months or more. Ask why it's been hard to fill, and whether anyone left it.

Green lights

Ramp or draw. It mentions a ramp period or guaranteed draw, so you're not on full quota from day one.
Pays accelerators. Higher commission rates once you pass quota. Overperformance actually pays.

Based only on what the posting says. Lights are a starting point for your first call, not a final judgment.

Questions to ask on the first call

Built from what this posting leaves out. How they answer tells you as much as what they say.

1.
This role has been open a while. What's made it hard to fill?
The answer tells you what candidates saw that made them walk.
2.
What percentage of fully ramped reps hit quota last year?
OTE is what you could earn. This is how likely you are to earn it.
3.
What percentage of reps on the team have been here more than 18 months?
Tenure shows whether people stay long enough to get paid.
4.
Has the comp plan changed in the last 12 to 18 months? What changed?
A plan that changes every year means the goalposts keep moving.
5.
Who sits with reps and reviews calls each week?
Coaching is often what's behind a good or bad attainment number.
6.
Why is this role open? Did someone leave, or is it new?
New headcount is growth. A replacement means someone left. Ask why.

› When the offer comes

Save these for later. They land better once they've said yes to you.

1.
Can I see the full comp plan in writing, including clawbacks and accelerators?
What's in writing is what gets paid. Read it before you sign.
2.
Can I see the actual comp distribution for the team last year, not just the OTE?
The spread shows what most reps really take home. OTE is just the target.
3.
I'd be walking away from earned commission to join. Is there room for a sign-on bonus to help cover that?
Leaving money behind is a fair reason to ask. The worst answer is no.

Josh's top five questions for any sales interview →

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Full 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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