Founding Account Executive

Founding Account ExecutiveA 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 SkipUpWe're building the next generation of scheduling software and infrastructure. The first generation gave people booking links. The second 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 RoleWe'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 IfYou'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 audienceYou want to work in a small team and with the founders and directly shape the go-to-marketRequirements3+ years of full-cycle SaaS sales experienceTrack record of building meaningful relationshipsHitting sales targetsExperience selling to RevOps, Sales, or Customer Success departments at B2B software companiesBonus PointsYou've sold scheduling, productivity, or workflow tools and have a robust network of professionals who value your opinion on these toolsYou understand the importance of slick customer purchasing workflowsYou were a top-performing BDR before moving into a closing roleReasons Not to ApplyYou want to inherit a pipeline or a book of businessYou're not comfortable running your own product demosYou prefer a structured environment with SDR support, enablement, and an established playbookInterview ProcessIntro 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)

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