Program Manager, AI Transformation

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. **Position Overview** Trunk Tools is looking for an experienced Program Manager to own the delivery of our AI-Enabled GC program inside our largest general contractor accounts. This is the person who runs the entire transformation: the project plan, the meeting cadence, the stage-gates, and the KPIs that prove it’s working. You’ll be dedicated to top-20 GCs for multi-year engagements, co-owning the account with the Customer Success Manager, who holds the commercial and renewal relationship. You’ll orchestrate a dedicated delivery pod — Forward Deployed Experts and the shared Instructional Design and Learning Operations team — to move an entire organization from AI-curious to AI-first. Travel is required for this position, up to 30%. **Key Responsibilities** - **Program Ownership & Execution** - Own the end-to-end program plan across every phase and keep the critical path on track. - Run the stage-gate model: define entry and exit criteria for each phase and hold the program to them. - Manage risk, dependencies, and resourcing across the pod, and make the calls that keep the deployment moving. - **Governance & Cadence** - Stand up and run the program’s meeting rhythm — executive steering committees, business-unit working sessions, champion syncs, and office hours. - Own executive alignment: keep the customer’s sponsor and leadership engaged, informed, and accountable to their commitments. - Lead program business reviews that show progress against KPIs and set the next quarter’s priorities. - **KPIs, Measurement & Reporting** - Define and track the adoption and behavioral-change metrics that prove the program is working — certification rates, active usage, and workflow change by business unit. - Correlate broad AI adoption with Trunk Tools outcomes, and report both to the customer and internally. - Maintain the executive dashboard and keep a single source of truth for program health. - **Team Orchestration** - Direct the day-to-day work of the delivery pod — the FDX Manager and Forward Deployed Experts, plus the shared Instructional Design and Learning Operations team. - Coordinate customer champions and trainers so the organization builds its own capability. - Make sure content authoring is resourced and started early — it sits on the critical path before the field can deploy. - **Handoff & Repeatability** - Drive the program toward a self-sustaining state — customer-owned trainers, governance, and cadence — by the end of the engagement. - Feed what you learn back into the shared playbook so the next GC deployment starts faster. **Qualifications** - **Experience** - 6+ years in program management, engagement management, or technical program management, including large, multi-stakeholder enterprise programs. - Direct experience leading change management or transformation programs — moving people and organizations, not just shipping software. - Customer-facing delivery experience (professional services, consulting, or enterprise CS). Construction, AEC, or enterprise SaaS is a strong plus. - **Skills & Knowledge** - Fluent in program-management practice and tooling (e.g., Asana, Smartsheet); PMP or Agile certification a plus. - Grounded in change-management methodology (e.g., Prosci / ADKAR); able to design cadence, stage-gates, and adoption metrics from scratch. - Strong executive presence — can hold a room of C-level stakeholders accountable and keep them aligned. - A daily AI power-user who leads by example, plus comfort with CS platforms (e.g., Planhat). - **Education** - Bachelor’s degree or equivalent experience. - Program-management or change-management certifications (PMP, Prosci, or similar) are a plus. **Why Trunk Tools?** - **Innovative Culture:** Work at the forefront of technology with a team that values innovation and continuous learning. - **Impactful Work:** Help transform businesses with tools that drive real, measurable outcomes. - **Career Growth:** Be part of a growing company with ample opportunities for personal and professional development. - **Competitive Compensation:** We offer a competitive salary, benefits, and performance-based incentives. - **Work-Life Balance:** Enjoy a supportive work environment that encourages a healthy work-life balance. **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 **@***[******](http://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.*