Program Manager, AI Transformation

Trunk Tools, Inc.•New York, NY

1d•$210,000 - $261,000•Hybrid

About The Position

Trunk Tools is seeking an experienced Program Manager to lead the delivery of their AI-Enabled GC program within their largest general contractor accounts. This role involves managing the entire transformation process, including project planning, meeting cadences, stage-gates, and key performance indicators (KPIs). The Program Manager will be dedicated to top-20 GCs for multi-year engagements, working alongside the Customer Success Manager. They will orchestrate a dedicated delivery pod, including Forward Deployed Experts and the Instructional Design and Learning Operations team, to transition organizations from being AI-curious to AI-first. Travel is required for this position, up to 30%.

Requirements

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).
Fluent in program-management practice and tooling (e.g., Asana, Smartsheet).
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).
Bachelor’s degree or equivalent experience.

Nice To Haves

Construction, AEC, or enterprise SaaS experience is a strong plus.
PMP or Agile certification is a plus.
Program-management or change-management certifications (PMP, Prosci, or similar) are a plus.

Responsibilities

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.
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.
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.
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.
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.