Account Executive, Enterprise
Canada · Full Time
Every organization runs on three things: the projects it's driving, the knowledge it keeps, and the requests it fields. And we are building it for a future where humans and AI agents do that work together.
Plane began in public on GitHub at the end of 2022. Since then it has grown into a work management platform used by teams around the world: 55,000+ stars, 5,000+ forks, and a contributor community that reads our code and files our issues. Organizations run Plane as a managed Cloud service, on their own infrastructure, or inside fully isolated environments. Building in the open keeps us close to users and raises the standard for everything we ship.
Plane is the #1 work infrastructure in aerospace, defense, financial services, and other regulated industries: organizations whose requirements for control, auditability, and data residency rule most software out. Adoption is growing fastest on Plane Cloud and in sovereign clouds, deployments that keep everything inside a country's own borders and rules.
We work in tightly knit teams, stay close to users, and care about the visible product as much as the unglamorous details that make software dependable. People own problems end to end, and we add process only when it helps the work.
Not agents replacing people, and not a chat window bolted onto software built for humans clicking around, but both working in one system of action, where an agent's work is as visible and as accountable as a person's.
Most software treats AI as a feature. This is what the infrastructure is for: making the future where humans and agents work together practical, legible, and fully within the organization's control. Every role at Plane is some part of building that.
The commercial demand is real and growing. 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. 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. That means security questionnaires, compliance reviews, legal redlines, multi-stakeholder approval chains, and timelines measured in months, not days. 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. 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'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'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 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.”
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.
Something you ship this month will run inside a Fortune 500 company and a 50-person startup in the same week, and you will hear from both.
Plane runs in our cloud, in customers' clouds, and on machines that will never touch the internet. Much of the work happens in the open, where the issues, the fixes, and the roadmap conversations are public. Building software that survives all of that is harder than building an ordinary SaaS product, and it is a better education than most companies can offer.
We are building that system now, for customers who already depend on it, and you will work on that problem directly whatever your role.
We do not discriminate based on race, color, religion, gender identity or expression, sexual orientation, national origin, age, disability, veteran status, or any other protected characteristic under applicable law.

📌 Account Manager - Full Time (Ottawa)
🏢 plane
📍 Ottawa