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