Founding Account Executive, Toronto - Remote

Founding Account Executive

A zero-to-one sales role for someone who wants to sell AI tooling and enterprise wide scheduling infrastructure, work directly with founders, and help define the GTM motion from scratch.

About SkipUp

· We’re building the next generation of scheduling software and infrastructure. The first generation gave people booking links. The second gen routed form submissions to calendars. SkipUp is an AI scheduling assistant that owns the end to end scheduling workflow, it joins the email thread, negotiates times with every participant, follows up on its own, and books the meeting.

· Connects to Google Calendar, Microsoft Calendar, Zoom and Slack.

· Product is live, customers are paying, interest from midmarket/enterprise clients exists.

· Three-person founding team, product-led, shipping non-stop.

· You can find out more at SkipUp.ai or sign up for a free account to try it out.

About This Role

We’re hiring our first GTM hire / founding Account Executive to drive midmarket and enterprise sales. You’ll own the full cycle: finding prospects, running demos, closing deals, and feeding what you learn back to the product team. Your buyers are GTM/RevOps leaders at mid-market B2B companies (50–5,000 employees) who lead teams that waste hours coordinating meetings.

You’d be working directly with the founders every day to figure out what works. This is a ‘founding GTM’ role with real equity and direct influence on how we go to market.

You Could Be a Great Fit If

· You’ve run full-cycle deals before: sourced the lead, ran the demo, closed the deal, handled onboarding.

· You’ve sold a product where the buyer wasn’t looking for it yet. You know how to create demand, not just capture it.

· You write clear, short outbound emails that get replies.

· You’re genuinely interested in AI and believe it will change how software and work get done.

· Comfortable demoing a technical product to a non-technical audience

· You want to work in a small team and with the founders and directly shape the go-to-market

Requirements

· 10+ years of full-cycle SaaS sales experience

· Track record of building meaningful relationships

· Hitting sales targets

· Experience selling to RevOps, Sales, or Customer Success departments at B2B software companies

Bonus Points

· You’ve sold scheduling, productivity, or workflow tools and have a robust network of professionals who value your opinion on these tools

· You understand the importance of slick customer purchasing workflows

· You were a top-performing BDR before moving into a closing role

Reasons Not to Apply

· You want to inherit a pipeline or a book of business

· You’re not comfortable running your own product demos

· You prefer a structured environment with SDR support, enablement, and an established playbook

Interview Process

· Intro call with CEO/Founder – (30 min)

· Product walkthrough with CTO/Founder - (60 minutes)

· Team meeting and social chat – (45 min)

· Reference call - (5-15 mins)

Compensation

· Equity: Meaningful early-stage equity

· Health Benefits