GTM Engineer

Build & own pipeline across paid, outbound, and content.

$150k-$180k + options

San Francisco

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I’m Cole, Head of Demand Generation at Plain. We’re redefining customer support for the next generation of B2B companies. We’re building the fastest, most powerful platform to help companies move beyond reactive support and build true customer relationships.

Some of the world’s most forward-thinking companies, like Cursor, Ashby, and Sanity, trust Plain to unify all customer interactions, enable faster team collaboration, and supercharge their workflows with AI.

We’re a small, tight-knit crew with offices in SF and London. This role is hybrid with 3 days a week in our SF office.

Why this role is special

B2B customer support is undergoing a seismic shift. AI is transforming the way companies engage with customers, shifting support from a siloed function to a company-wide effort across Slack, Discord, and in-product experiences.

Plain is leading the charge in building this new world, and the GTM Engineer owns how we turn that vision into pipeline across paid, outbound, and content. You'll have real budget, real autonomy, and a major finger on the scale of revenue.

You'll be one of the first hires on a GTM team we're building from scratch. The vision is a small, technical, high-output team that treats marketing like a product: instrumented, iterative, and AI-native.

What you'll do

You’ll spend 100% of your time generating pipeline with minimal guardrails and a lot of room to experiment.

Day to day, you will:

Build and scale repeatable signal-based outbound to generate net-new pipeline through experimentation and optimizations.
Create LLM-powered content that ranks highly in SEO and AI search (we call this Generative Engine Optimization aka GEO).
Report on successes and improvements with constant iteration.
Write copy that converts — landing pages, ads, and emails that feel like they were written by someone who actually understands the product and buyer.
Instrument everything so we know what’s working (and what’s not), and use that feedback loop to ship better, faster.

This is a great fit if you…

You have strong sales acumen and write copy that converts (without AI) - landing pages, ads, and emails that feel like they were written by someone who understands the product and buyer.
You’ve been testing and honing your skills with the latest AI and workflow automation tools (n8n, Unify, Claude Code, Clay, Instantly, etc.)
Have a builder mentality and care more about what we can ship this week than a perfect Q4 plan.
Are a little technical and very curious — comfortable with APIs, light coding, and connecting systems to unlock new GTM motions.
Are an obsessive experimenter who is happiest when testing, iterating, and letting results guide your time and energy.

This won't be the right role if you…

Need a detailed playbook handed to you instead of helping write it. We’ve had success, but are very much an early stage company looking for creativity and differentiation.
Optimize for process over output.
Prefer "big company" environments over fast-moving, hands-on work.

The salary range for the role is $150k - $180k + equity. The salary range shown is intentionally broad to reflect the range of skills and levels that we are open to for this role. Your placement within in the salary range will be decided upon completion of the interview process, taking into account factors like your demonstrated skills, and the depth of your experience. Our Recruiting team will be able to provide more details during the interview process.