GTM Engineer

We believe the next decade of work will be done by humans and AI agents together. 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. We treat agents as a kind of worker, and that changes what the system underneath has to be. Agents are only as good as the context they can see and the state they are allowed to change, so shared context, explicit state, durable history, and accountable action are not items on our roadmap. They are the product. Plane is built so that when an agent acts, the humans responsible can see what happened, why, and on whose authority, and the record survives.

This is what the infrastructure is for: making the future where humans and agents work together useful, legible, and fully within the organization's control. Every role at Plane is some part of building that.

This is the first dedicated GTM engineering hire at Plane, and you will build the function from the ground up. You own outbound end to end: ICP definition, enriched lists, sequences, sending infrastructure, and the reply routed to Sales with the context intact. The audience is the constraint. Plane sells to engineering, product, and IT teams, and to buyers with compliance and self-hosting requirements, and they delete generic outreach without opening it. You will work with Sales on what happens after the meeting is booked, with Marketing on message and offer, and with Engineering on access to the product telemetry your triggers read.

Own outbound end to end and carry the number: qualified meetings and pipeline from cold, repeatably, at a known cost per meeting.

Turn Plane's own signals into trigger-based plays. GitHub activity, Docker pulls, self-hosted installs, community threads, funding, and hiring are intent data most companies in our category cannot see, and turning them into timed plays is your job.

Segment by deployment motion as well as by firmographics. Cloud, self-hosted commercial, and air-gapped buyers have different objections, different security reviews, and different reasons to answer.

Own sender reputation across every domain and inbox you run: warmup, rotation, SPF, DKIM, DMARC, blocklist monitoring, and keeping cold infrastructure isolated from the primary domain.

Build agents and systems that do account research at a volume no person can match. Wire LLM providers into the stack, and write your own tooling where Clay, the CRM, or a sequencer stops.

Work daily with Sales on reply quality and handoff, with Marketing on message and offer, and with the engineers who own the telemetry your triggers read.

Spend real time on maintenance: pruning dead records, chasing a bounce rate that moved two points, rebuilding a list after a provider degraded, and killing a sequence you wrote because the data says it does not work.

You have run cold outbound that produced pipeline. You can name the segment, the volume, the reply rate, and what you changed when the reply rate dropped.

You have built in Clay or an equivalent orchestration platform. Enrichment waterfalls, provider fallbacks, and cost per enriched record are things you have tuned, not read about.

You treat deliverability as infrastructure Domains, warmup, rotation, SPF, DKIM, and DMARC, and what you do in the first hour after spam placement moves.

You have shipped with LLM providers, not just prompted them You have wired Anthropic or OpenAI models into a working system and handled what happens when the output is wrong.

You can connect systems yourself SQL, APIs, webhooks, and enough code to join a data layer to a CRM to a sequencer without waiting on an engineer.

You write for technical buyers You can explain why a message to a platform engineering lead reads differently from one to a VP of operations, and you can show replies from both.

You have run outbound for an open-source, open-core, or developer-facing product, for an audience that can read your code.

You have used Plane, run it self-hosted, or built prospecting around another open project's community signals.

You have sold into regulated or air-gapped environments and know how long a security review takes.

You have built agents that run in production without you watching them.

Data and enrichment: Clay, multiple contact and firmographic providers

Sequencing: multichannel cold email, HeyReach for LinkedIn

Sending infrastructure: dedicated domains, warmup and rotation tooling, SPF, DKIM, DMARC

AI: Anthropic and OpenAI models, plus agents we build on top of them

CRM and analytics: HubSpot, PostHog

Everyday tools: GitHub, Plane (yes, we run on it), Figma, Slack

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.

Plane is an equal opportunity employer. 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.