ABOUT PLANE

Plane is an incisive response to config-heavy, opinionated, and restrictive project management software. Read our 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.

Enterprise sales for Work infrastructure for Humans and Agents.

Plane has over a million users, and Fortune 500 companies deploying Plane. 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.

WHAT YOU'LL DO

Own the 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. You bring that signal back to the product team in a structured, actionable way — not as a feature request list, but as a pattern.

WHAT WE'RE LOOKING FOR

You, Ideally

• You've closed enterprise software deals in the $500K–$1M ACV range, running the full cycle yourself — not inheriting qualified pipeline from a BDR team or handing off to a solutions engineer for the technical conversation.

• You've sold into technical buyers — engineering leadership, DevOps, IT — and you can have a real conversation about deployment models, infrastructure, and security without reading from a script. You understand the difference between selling to someone who writes code
  and selling to someone who writes checks.

• You've worked at an early-stage company (Series A or earlier) where the sales infrastructure didn't exist yet. You've built your own pipeline, written your own sequences, created your own collateral, and figured out the motion before it was documented.

• You understand product-led growth and know how to work with it rather than against it. You don't fight the free tier — you see it as the top of your funnel and know how to identify when a user is ready for an enterprise conversation.

• You're comfortable with long deal cycles and multi-stakeholder procurement processes. You don't get rattled when a deal takes 4 months and involves legal, security, compliance, and IT all having veto power.

• You're structured in how you manage your pipeline, your notes, and your follow-ups. Not because someone made you use a CRM, but because you've learned that rigor is what separates someone who closes from someone who's "always about to close."

• You can write. Not marketing copy — clear, concise follow-up emails, proposals that address the buyer's actual concerns, and internal summaries that help the team understand what the market is telling you.

What we offer

• The opportunity: Plane is at the start of its enterprise chapter. You'll help define the commercial motion of a product already used by over a million people and running in production at some of the world's most demanding organizations — including in regulated, air-gapped, and classified environments.

• Compensation: Base salary, uncapped commission, and meaningful equity. The people who build Plane should own a piece of it.

• Impact over hierarchy: We're a small team shipping fast. Your work moves the product, the company, and the category — not through a chain of approvals.

• Annual offsite: Once a year, the entire team gets together in person to plan, connect, and celebrate what we've built.

• Learning & development: An annual stipend to invest in your craft — conferences, courses, books, or coaching.

• Co-working stipend: A monthly allowance to work from a co-working space when that's how you do your best work.

• Home office setup: A stipend to build the workspace you need to be effective from day one.

• Health & benefits: Comprehensive health insurance and benefits for you and your dependents.

The pipeline is real: This isn't a prospecting job. On day one, we'll walk you through the enterprise conversations already in motion — real accounts, real buyers, real deal cycles. Your first weeks are about closing, not cold-starting.