[Hiring] Founding Account Executive @skipup

Role Description

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.

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
• 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.

Qualifications

• 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