Position OverviewTrunk 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
@trunk.tools. If you receive outreach from any other domain, please disregard it or report it to us.
