Construction Subject Matter Expert; SME

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.

Location: New York City or Austin

We’re looking for an experienced Construction Subject Matter Expert (SME) to embed with our Product & Engineering teams and make our AI products measurably better for construction professionals every day. This is not a sales role. You are the bridge between how construction actually works — in the field and the back office — and how our AI agents need to reason, behave, and prove their value.

You’ll spend your days translating deep construction expertise into ground truth, evaluations, product feedback, and experiments — and translating what the product can do back into a value story the field and the C‑suite both believe.

This role has two modes, and you need to be comfortable in both. Most of the time you’re embedded with Product & Engineering, building the rigor that makes our agents trustworthy. But you’ll also be asked to embed directly on a customer’s jobsite as a hybrid member of their project team — deploying and refining AI‑powered workflows on a live project and acting as the front line for how the product lands in the real world.

If running evals one week and commanding a room of superintendents on a project walkthrough the next sounds energizing rather than jarring, this is your role.

• Build ground truth and evaluation datasets. Define what “correct” looks like for our AI agents on real construction documents and workflows, and develop the labeled datasets and evals that let us measure and improve agent quality with rigor.

• Test the product like a construction expert would. Run structured product testing against real‑world project data, catch where the AI gets construction wrong, and give Product & Engineering precise, actionable feedback — daily.

• Embed on customer jobsites as a hybrid team member. Deploy and refine AI‑powered workflows across core construction operations, act as the primary point of contact between the customer’s field and office teams and Trunk Tools, and build and iterate on project‑specific workflows, document conventions, and output templates that match each customer’s reporting standards.

• Surface and close field friction. Identify and document friction points on real projects, bring them back internally, and work cross‑functionally with Product & Engineering to close the gaps.

• Triage and prioritize customer and user feedback. Assess incoming feedback for validity and severity, and judge how market‑pervasive each need is — distinguishing a one‑off project quirk from a pattern worth building for.

• Run experiments applying AI to construction. Constantly probe where our products can add value across construction workflows — submittals, drawings, RFIs, change orders, scopes, closeout, and beyond — and surface the highest‑leverage opportunities. You don’t just use AI tools; you find new ways to apply them for field…