Account Executive, Enterprise

Account Executive, Enterprise ABOUT PLANE Plane is an incisive response to config-heavy, opinionated, and restrictive project management software. Read our manifesto https://plane.so/manifesto. In just two years, Plane has grown to #1 in its category on GitHub and become a viable open-core alternative to Jira, Monday, Wrike, Asana, ClickUp, Linear. Our growth has come on the back of the product’s true flexibility without artificial limits, simple configurations that work out of the box, and thoughtfully packaged features that nurture our customers’ growth instead of punishing it. As a modern product start-up, we obsess over new and power users equally. Our mission is to empower teams everywhere with the simplest, most delightful work management experience on the planet. Our vision is to become the WorkOS of the future with a workbench of unified tools and techniques that intuitively and progressively form a greater whole for knowledge workers. ABOUT THE ROLE ENTERPRISE SALES FOR OPEN-SOURCE WORK INFRASTRUCTURE Plane has over a million users, 40,000+ GitHub stars, and 100K monthly active users. Enterprises in aerospace, defense, healthcare, and finance are running Plane in production — some in air-gapped, classified environments. The commercial demand is real and growing. This role exists to own it. You'll run full-cycle enterprise deals from first conversation to signed contract. You'll work directly with the CEO and the product team, because at this stage, a deal isn't just a sales process — it's a product feedback loop. You'll sell into technical buyers who already know the product, navigate complex procurement in regulated industries, and help build the playbook as you go. Plane's sales motion is product-led. The funnel doesn't start with cold outreach — it starts with teams already using Plane and hitting a ceiling where they need enterprise capabilities: compliance, SSO, air-gapped deployment, priority support. Your job is to convert that organic interest into expanding enterprise revenue. This is an early-stage sales role with real enterprise traction behind it. You won't be handed a mature pipeline, but you won't be starting from zero either. The product has pull — your job is to turn that pull into a repeatable commercial engine. WHAT YOU'LL DO OWN THE FULL CYCLE Run deals end-to-end — from first enterprise inquiry to signed contract. You own the entire arc: discovery, demo, technical evaluation, security review, procurement, negotiation, close. Full-cycle means full ownership. Convert product-led interest into enterprise revenue — Plane's funnel doesn't start with outbound. It starts with someone self-hosting Plane, hitting a scale or compliance ceiling, and raising their hand. Your job is to recognize those signals, engage at the right moment, and guide the conversation from "we're evaluating" to "we're deploying." Navigate complex enterprise procurement — our buyers sit in aerospace, defense, healthcare, and finance. That means security questionnaires, compliance reviews, legal redlines, multi-stakeholder approval chains, and timelines measured in months, not days. You need to know how to move a deal through that machinery without losing momentum. Hold technical credibility in the room — you'll be talking to VPs of Engineering, DevOps leads, and IT architects about self-hosted deployments, air-gapped environments, SSO configurations, and data residency requirements. You don't need to be an engineer, but you need to hold your own in these conversations and know when to bring one in. Build and refine the sales playbook — document what works. Which objections come up repeatedly? What's the typical deal cycle? Where do deals stall? What collateral is missing? You're not just selling — you're creating the system that the next 3-5 AEs will run on. Feed product with deal intelligence — every deal you run generates signal about what the market wants, what competitors are doing, and where Plane has gaps. Yo ... (truncated, view full listing at source)