Location: New York City or San Francisco (Austin considered as alternate, then remote)

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 or customer-success 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.

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.
• 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.
• 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. Must be comfortable with speaking confidently with executives.
• 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 connections with customers and prospects in the field and the executive back office to help educate and train.

Ideal background

• 10+ years on large commercial construction projects across varied types (life sciences/pharma, multi-family, mixed use, retail, industrial, etc.).
• Hands-on field and project leadership experience as a Superintendent, Project Manager, and/or Project Engineer - 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 explain complex construction processes clearly to engineers, designers, and PMs, 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, InEight, Kahua, 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.
• 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.

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.