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About the Role

Trunk Tools is seeking an experienced Program Manager to lead the delivery of our AI-Enabled GC program within major general contractor accounts. This role involves managing the entire transformation process, including project plans, meeting cadences, stage-gates, and KPIs, to transition organizations from AI-curious to AI-first. You will be dedicated to top-tier GCs for multi-year engagements, working closely with the Customer Success Manager and orchestrating a delivery pod of Forward Deployed Experts and support teams.

Responsibilities

Own the end-to-end program plan across all phases and maintain the critical path.
Manage the stage-gate model, defining and enforcing entry and exit criteria for each phase.
Oversee risk, dependencies, and resourcing within the pod to ensure deployment progress.
Establish and lead the program's meeting rhythm, including executive steering committees and working sessions.
Ensure executive alignment by engaging customer sponsors and leadership.
Lead program business reviews to report progress against KPIs and set future priorities.
Define and track adoption and behavioral-change metrics, such as certification rates and active usage.
Correlate AI adoption with Trunk Tools outcomes and report findings internally and externally.
Maintain the executive dashboard and ensure a single source of truth for program health.
Direct the daily work of the delivery pod, including Forward Deployed Experts and support teams.
Coordinate customer champions and trainers to build internal customer capability.
Ensure content authoring is resourced and initiated early, as it is critical for field deployment.
Drive the program towards a self-sustaining state with customer-owned trainers, governance, and cadence.
Contribute learnings to the shared playbook to accelerate future GC deployments.

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.
Customer-facing delivery experience (professional services, consulting, or enterprise CS).
Construction, AEC, or enterprise SaaS experience is a strong plus.
Proficiency in program management practices and tooling (e.g., Asana, Smartsheet).
Grounded in change management methodology (e.g., Prosci / ADKAR).
Strong executive presence to manage and align C-level stakeholders.
Daily AI power-user and comfort with CS platforms (e.g., Planhat).

Skills

Program Management
Engagement Management
Technical Program Management
Change Management
Transformation Programs
Customer-Facing Delivery
Enterprise SaaS
Asana
Smartsheet
Prosci / ADKAR
Executive Presence
AI
Planhat

Location

Remote
Hybrid
NYC
Austin

Work Type

Full-time
Remote
Hybrid

Experience Level

6+ years

Education Level

Bachelor's degree or equivalent experience.

Benefits

Competitive salary and stock option equity packages
4 Medical Plans to choose from including 100% covered option
Dental and Vision Insurance
Learning & Growth stipend
Flexible long-term work options
Free lunch provided in the office (NYC & Austin)
Unlimited PTO
IRL / In-Person retreats throughout the year

About the Company

Trunk Tools is the leading AI company revolutionizing the construction industry.
We have raised $40M in Series B funding, bringing total funding to $70M.
Our mission is to build the future of construction through intelligent automation.
Founded by builders and technologists from Stanford and MIT.
Our team has delivered software used by over 140,000 field professionals.
We are scaling fast and entering a period of hypergrowth with over 100 employees (50+ engineers).

Equal Opportunity

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.