Founding GTM Engineer — Trunk Tools

At Trunk Tools, we’re the leading AI company revolutionizing construction, the second-largest industry on earth. We recently raised a $40M Series B led by Insight Partners, bringing our total funding to $70M from top-tier investors including Redpoint and Innovation Endeavors. This new round is fueling our next phase of growth as we scale AI agents across the jobsite.

Our mission is to build the future of construction through intelligent automation. Despite being a $13+ trillion industry, construction still runs largely on analog processes, we’re changing that by embedding AI directly into field operations.

Founded by builders and technologists (Stanford, MIT), our team has delivered software used by over 140,000 field professionals, impacting millions of users and contributing to $10B+ in built projects. Many of us come from the field ourselves, giving us a deep understanding of the industry’s unique challenges.

After years of building the “brain” of construction, we’re now launching production-ready AI agents, starting with intelligent document processing and Q&A, and rapidly expanding into core operational workflows. Our team has doubled in the past year, and with 100+ employees (50+ engineers), we’re scaling fast and entering a period of hypergrowth. This is a rare opportunity to join at an inflection point.

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.

At Trunk Tools, we’re working hard to build a more productive and safer environment within the construction industry, and we strive to live by these same values here at Trunk Tools HQ. As an equal-opportunity employer, we are committed to building an inclusive environment where you can be you. We work hard to evaluate all employees and job applicants consistently, without regard to race, color, religion, gender, national origin, age, disability, pregnancy, gender expression or identity, sexual orientation, or any other legally protected class.