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.

What you’ll do

• 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 teams.

• Map and explain construction workflows. Visualize how work actually flows on commercial projects and teach it to technical and non-technical colleagues so the team builds with an accurate mental model of the field.

• Tell the value story at two altitudes. Articulate impact both at the construction field level (the superintendent, PE, or PM doing the work) and at the executive ROI level (schedule, budget, risk, margin) — internally to guide the roadmap and externally to make the value tangible. You can command a room of supers on a jobsite walkthrough and run a polished virtual meeting with project executives in the same week.

• Partner closely with Product & Engineering. Operate as a trusted, embedded expert who helps the team expand the value the product delivers across roles and levels in construction organizations.

• Travel 10–25% to job sites. Build trust with field teams and connections with executives in the back office, and stay close to how the product lands in the real world.

Ideal background

• 7+ years in commercial construction, with deep field-operations experience carrying the most weight. We care more about how thoroughly you’ve lived the workflows than about title or tenure. Experience across varied project types (life sciences/pharma, multi-family, mixed use, retail, industrial, etc.) is a plus.

• Hands-on field and project leadership experience as a Superintendent, Project Manager, Project Engineer, or APM — you’ve lived the workflows we’re automating.

• A genuine AI experimenter. You actively use AI and LLM tools, you’re curious about how to apply them, and you reach for experimentation as a first instinct — not just a construction-tech early adopter, but someone energized by what AI can do for the industry.

• A teacher and translator. You can write a clean owner report and explain a complex AI output to a skeptical superintendent in the same day, and you’re equally comfortable reasoning about field-level value and executive ROI.

• Deep construction-tech fluency. You’ve extensively used construction PM tools (Procore, Autodesk/ACC, BIM 360, P6, InEight, Kahua, Bluebeam, etc.) and document management solutions (SharePoint, ACC, etc.), and you’ve played an active role in implementing software at the companies where you’ve worked.

• Comfortable operating in ambiguity. You’re the kind of person who figures out what “done” looks like before anyone tells you.

• A strong collaborator who works effectively across technical and non-technical teams, learns fast, and drives outcomes with minimal supervision.

• Strong written and verbal communication and a clear bias toward action — you gravitate to environments where you can have outsized influence on outcomes for customers and colleagues.

• Bonus: experience in a customer-facing or solutions role (SE, CSM, implementation) alongside your field background.

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.