Founding GTM Engineer
About The Position
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. This is a Hybrid role based out of our NY Office.
Requirements
- 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 Haves
- 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
Responsibilities
- 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.
Benefits
- 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
- Unlimited PTO
- IRL / In-Person retreats throughout the year
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What This Job Offers
Job Type
Full-time
Career Level
Entry Level
Education Level
No Education Listed
