Our largest customers do not buy Plane off the shelf. A bank wants it behind their firewall with SSO tied to their identity provider; a defense contractor wants it air-gapped with a migration plan from three legacy tools at once. You will own the technical architecture for these deployments before the contract is signed and after, translating what a customer's infrastructure and compliance team requires into a Plane deployment that actually holds up. You will work directly with sales on the largest deals we run and with engineering when a customer's requirements push past what we support today. This role exists because our regulated-industry customers ask questions our sales team cannot answer alone, and our engineers should not have to answer on every call.

• Own the technical architecture for enterprise and regulated-industry deployments, from the first discovery call through a signed statement of work.
• Design self-hosted and air-gapped Plane deployments that satisfy a specific customer's security review, not a generic best-practice checklist.
• Run technical discovery with customers whose infrastructure and compliance teams will pick apart every answer you give, and be right often enough that they trust the next one.
• Define the migration path when a customer moves off two or three existing tools at once, including what data does not survive the move and saying so up front.
• Work daily with sales on live deals and with engineering when a customer's requirements expose a real gap in the product, carrying that gap back as a specific, scoped request rather than a vague one.
• Answer the same security questionnaire in a slightly different format for the fourth time this month, because every regulated buyer's procurement process is its own small bureaucracy and none of them read each other's paperwork.

What you'll bring

• You have designed and defended a technical architecture to a skeptical buyer , and you can walk us through one deal where the customer's own security or infrastructure team changed your design.
• You understand self-hosted and on-premises deployment beyond a docker-compose file , including networking, SSO and identity federation, and what changes when a customer runs the software instead of you.
• You can read a security questionnaire or compliance requirement and translate it into an actual deployment decision , not a reassurance.
• You are comfortable being the technical voice on a sales call , including the parts where the answer is no or not yet.
• You write technical documentation a customer's own engineers will actually follow , because you will not be in the room when they run it.

Nice to haves

• You have worked pre-sales or post-sales in a solutions architecture, sales engineering, or technical account management role selling to regulated industries.
• You have contributed to Plane, run it self-hosted, or maintained another open project people rely on.
• You have shipped or supported deployments into banking, defense, healthcare, or air-gapped environments specifically.
• You have opinions about how AI agents should be permissioned and audited in an enterprise environment, and can defend them.

Tech

• Backend : Python/Django, Golang, Node.js, Postgres, Redis
• Messaging : RabbitMQ, Kafka
• Infrastructure : AWS, Kubernetes, Rancher, self-hosted deployment via Docker and Helm
• Identity : SAML, OIDC, SCIM
• Everyday tools : GitHub, Plane (yes, we run on it), Figma, Slack

Why Plane?

Every company says it is different. We will try evidence instead.

The scope is real. We are a passion team serving companies of every size, including some of the largest in the world. 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.

The constraints make you better. 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.

The people-and-agents future is being built here, in production. We think humans and AI agents will share one system of action for work. We are building that system now, for customers who already depend on it, and you will work on that problem directly whatever your role.

Your name is on the work. The teams are deeply connected enough that credit and responsibility both find you fast. That is some pressure. Mostly it is the fun part.

If that sounds like your kind of place, we would like to meet you.

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