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Trunk Tools is a Series B AI company ($70M total funding, $40M Series B led by Insight Partners) revolutionizing construction through intelligent automation. The company has 100+ employees (50+ engineers) and serves 140,000+ field professionals across $10B+ in built projects. Founded by builders and technologists from Stanford and MIT, Trunk is scaling rapidly and entering hypergrowth as it launches production-ready AI agents for jobsite operations.
You will be Trunk's first Founding GTM Engineer, sitting at the intersection of product, sales, marketing, customer success, and engineering. This is a builder role with outsized ownership—you'll design and own the internal "AI operating system" that powers the entire go-to-market funnel, treating GTM tooling as a product you build, ship, measure, and iterate on.
Key responsibilities:
- Own the GTM AI OS end-to-end: gather requirements from GTM leaders, prioritize across functions, build, ship, measure, and iterate on the internal toolset the whole organization depends on.
- Build workflow automation across the full funnel: design systems that move accounts from raw signal through enrichment, scoring, routing, and outbound orchestration with minimal manual steps, extending into post-sale handoffs.
- Build and own the AI-orchestration layer: develop internal agents for account research, personalization, qualification, call summarization, and analysis at scale, using LLMs and agents as core infrastructure.
- Co-own data architecture and pipeline: shape the GTM data foundation and pipeline alongside engineering and a planned data-engineering hire.
- Manage stack ownership: evaluate new tools, manage vendor relationships, and recommend stack changes as the company scales.
In the first 90 days, you'll map the current GTM stack and ship 1-2 automation quick wins, stand up the first end-to-end automated workflow (signal → enrichment → scoring → routing), layer in the first AI-orchestration step, partner on the shared data foundation, and publish a prioritized roadmap for the GTM AI OS focused on demand/pipeline generation and quote-to-cash optimization.
This is a pseudo-internal PM position requiring both deep technical capability and commercial curiosity. You'll operate in a fast-paced, ambiguous, execution-focused environment with full end-to-end ownership.
REQUIREMENTS:
- AI-fluent and current with frontier models, tools, API calls, and MCPs; able to turn them into working automations daily.
- Strong business sense: can dive into real-world GTM problems, reason about tradeoffs, and identify what moves the needle.
- Exceptional communication: frame problems clearly, explain thinking crisply, translate between technical and commercial audiences.
- Builder's instinct for workflow automation and tool development: move from messy business problems to working systems quickly without waiting for a playbook.
- Product mindset: able to prioritize, scope, and ship the right thing for internal customers across GTM.
- Comfort in fast-paced, ambiguous, execution-focused environments with end-to-end ownership.
NICE-TO-HAVE:
- GTM strategy or operations background (RevOps, sales ops, growth).
- Hands-on experience with GTM AI automation tools (Clay, Claude, Zapier, etc.).
- Experience building and deploying AI agents or agentic workflows.
- Early-stage startup experience.
- Direct sales, SDR, or customer-facing exposure.
- Construction, AEC, or vertical-SaaS industry familiarity.
