About the role

Trunk Tools is hiring its first Founding GTM Engineer to build the workflow automation and AI orchestration that powers our entire go-to-market funnel. You'll sit at the intersection of product, sales, marketing, customer and engineering - acting less like a traditional operator and more like a systems engineer for revenue generation. This person will design and own the internal "AI operating system" that all of GTM at Trunk runs on: the automated workflows and the AI-agent layer that turn repeatable manual work into systems.

This is a builder role with an outsized amount of ownership. In many ways it's a pseudo- internal PM position: you'll decide what to build, prioritize across GTM functions, and ship the tooling the whole org depends on. It's deeply technical - you should be as capable as a strong software engineer - but the best person for it is also curious about the commercial side and, ideally, brings GTM strategy or ops experience of their own.

This is a founding seat: you'll be part of building the highest-leverage GTM ops team in the AI space.

What you'll own

• The GTM AI OS, end to end: treat the internal GTM toolset as a product. Gather requirements from GTM leaders, prioritize across functions, build, ship, measure, and iterate - the AI operating system the whole org runs on.
• Workflow automation across the full funnel: build systems that take an account from raw signal through enrichment, scoring, routing, and outbound orchestration with no manual steps in between - and extend the same automation into post-sale handoffs.
• AI orchestration: build and own the AI-agent layer - internal agents for account research, personalization, qualification, call summarization, and analysis at scale. You'll reach for LLMs and agents as core infrastructure, not novelty.
• Data architecture & pipeline (co-owned): you'll have a real hand in the GTM data foundation and pipeline that everything else runs on. This is co-owned with engineering and a planned data-engineering hire - you shape and depend on it, but you won't carry it alone.
• Stack ownership: evaluate new tools, manage vendor relationships, and recommend stack changes as we scale.

What the first 90 days look like

• Map the current GTM stack and the manual workflows the team runs today, and ship one or two visible automation quick wins
• Stand up the first end-to-end automated workflow: signal → enrichment → scoring → routing
• Layer in the first AI-orchestration step - an internal agent for research, personalization, or summarization
• Partner with engineering and the data-engineering hire on the shared data foundation underneath it all
• Publish a prioritized roadmap for the GTM AI OS, with early wins measured against our two anchor outcomes: demand / pipeline generation and attribution, and quote-to-cash optimization

Must-have qualifications

• AI-pilled and fluent with the frontier - you use the latest models, tools, API calls, and MCPs daily, and you know how to turn them into working automations
• Strong business sense - you can dive into a real-world GTM problem, reason about tradeoffs, and figure out what actually moves the needle
• Exceptional communication - you frame problems clearly, explain your thinking crisply, and translate between technical and commercial audiences
• A builder's instinct for workflow automation and tool development - you go from a messy business problem to a working system fast, without waiting for a playbook
• A product mindset: able to prioritize, scope, and ship the right thing for internal "customers" across GTM
• Comfort in a fast-paced, ambiguous, execution-focused environment where you own outcomes end to end

Nice-to-have qualifications

• GTM strategy or operations background (RevOps, sales ops, growth) - a real plus, not a requirement
• Hands-on experience with the latest and greatest GTM AI automation tools - Clay, Claude, Chat, Zapier, and similar
• Experience building and deploying AI agents / agentic workflows
• Early-stage startup experience (comfort with ambiguity, no playbook)
• Any direct sales, SDR, or customer-facing exposure
• Construction, AEC, or vertical-SaaS industry familiarity

Explicitly not required

• Prior GTM Engineer title
• Deep pre-existing expertise in any specific automation tool (you'll pick these up fast)

What we offer

A close-knit and collaborative early-stage startup environment where every voice is heard and every opinion matters

Competitive salary and stock option equity packages

4 Medical Plans to choose from including 100% covered option. Plus Dental and Vision Insurance!

Learning & Growth stipend

Flexible long-term work options (remote and hybrid)

🥨 Free lunch provided in the office in NYC & Austin - you'll never go hungry with us!

Unlimited PTO; We truly believe in work-life balance and that hard work should be balanced with time for rest and rejuvenation

IRL / In-Person retreats throughout the year

Please note: All official communication from Trunk Tools will come from an email address ending in @trunk.tools. If you receive outreach from any other domain, please disregard it or report it to us.