Founding Account Executive, Middesk

• 4+ years of quota-carrying experience in B2B SaaS (startup or early-stage preferred) with success selling new products or opening new markets
• Experience with AI, automation, or agentic workflow software — you understand how these technologies solve real problems and can speak credibly with technical buyers
• A founder mindset: ownership, adaptability, and the ability to create structure without waiting for direction
• Bias toward action and experimentation; you move quickly and use customer learning loops to guide decisions
• Deep curiosity and pattern recognition; you ask sharp questions and turn feedback into strategy
• Product intuition and confidence collaborating with technical teams to shape features and narratives
• Full-cycle sales excellence: discovery, solutioning, stakeholder alignment, negotiation, and closing
• Cultural alignment: low-ego, high-output, collaborative, and driven by meaningful impact

Desirable

• We’re hiring a Founding Account Executive to launch Middesk’s new agent AI product — a platform built to automate complex workflows that companies currently rely on people to manage
• This is a ground-floor role with direct influence over what the product becomes, how we bring it to market, and how quickly it scales
• You won’t inherit a playbook. You’ll write it
• You’ll be the person who turns early signals into revenue, shapes how customers experience the product, and materially influences Middesk’s next chapter
• Your fingerprints will be on everything from our first lighthouse accounts to the early GTM systems that future teams build upon
• If you’re motivated by outsized ownership, steep learning curves, and seeing your work translate into real business impact, this role offers a rare chance to build something new alongside a deeply technical, high-output team
• Identify and engage early-adopter segments; use customer discovery to validate problems and sharpen positioning
• Run light, fast experiments (messaging, ICP hypotheses, channels, pricing) to learn where the product resonates
• Do targeted market research to understand workflows, competitive signals, and where the strongest use cases emerge
• Own the full sales cycle — from first outreach through close and onboarding
• Build early GTM motions grounded in what you learn from conversations, experiments, and data
• Partner closely with Product and Engineering to turn customer insight into roadmap priorities
• Create foundational GTM materials: personas, pitch decks, ROI stories, demo flows
• Establish the systems, metrics, and playbooks that future AEs will scale