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Jobs · Information Technology · New York

Program Manager, AI Transformation

Trunk Tools · New York, NY · 1 mo ago
On-siteInformation Technology$210k–$261k/yrFull-time

Position Overview

Trunk Tools is seeking a Program Manager to lead the transformation of our AI-Enabled GC program within the largest general contractor accounts. This role involves running the entire transformation, managing the critical path, and ensuring successful execution.

Key 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.

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).

  • 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.

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