Engagement Manager

Engagement Manager

At Trunk Tools, we're the leading AI company revolutionizing construction the second‑largest industry on earth. We recently raised a $40M Series B led by Insight Partners, bringing our total funding to $70M from top‑tier investors including Redpoint and Innovation Endeavors. This new round is fueling our next phase of growth as we scale AI agents across the jobsite.

Our mission is to build the future of construction through intelligent automation. Despite being a $13+ trillion industry, construction still runs largely on analog processes; we're changing that by embedding AI directly into field operations.

Founded by builders and technologists (Stanford, MIT), our team has delivered software used by over 140,000 field professionals, impacting millions of users and contributing to $10B+ in built projects. Many of us come from the field ourselves, giving us a deep understanding of the industry's unique challenges.

After years of building the "brain" of construction, we're now launching production‑ready AI agents starting with intelligent document processing and Q&A, and rapidly expanding into core operational workflows. Our team has doubled in the past year, and with 65+ employees (25+ engineers), we're scaling fast and entering a period of hypergrowth – this is a rare opportunity to join at an inflection point.

As an Engagement Manager, you'll be the frontline partner helping customers implement AI workflows that stick. This is a high‑touch, high‑impact role focused on value delivery, behavioral change, and workflow transformation. You'll help customers embed AI into their daily operations not just try it, but trust it. Engagement Managers are the voice of the customer: uncovering explicit and implicit business needs and collaborating with Product to shape the roadmap.

We're looking for someone who brings strategic thinking, executional rigor, and curiosity as we write the playbook for deploying enterprise AI in the built world.

• Customer Embedding:
  Act as the day‑to‑day partner for strategic logos, shadow workflows, build trust with field teams and executives, and co‑design impactful AI solutions
• Workflow Design & Deployment:
  Map and translate construction workflows into structured implementations; configure AI agents, test data flows, and activate jobsite teams
• Training & Enablement:
  Develop curriculum and run live workshops, certify customer "champions" to scale adoption and drive executive level change
• Customer Advocacy:
  Gather detailed qualitative and quantitative feedback; synthesize insights and present recommendations for Product and Engineering to drive roadmap alignment
• Metrics & Reporting:
  Define adoption KPIs, report on time saved, and track success across project milestones
• Cross‑functional Execution:
  Coordinate with Sales, Product, Engineering, and CX to deliver a seamless customer experience and identify upsell opportunities

• 5+ years of experience in Construction AND Technology, ideally within innovation, ops, or field deployment teams
• Strong track record of driving technology adoption and behavior change within complex customer orgs
• Comfortable working across business and technical audiences – you can translate field needs to product requirements and vice versa
• Technical curiosity – comfortable working with cloud‑based tools, APIs, LLM workflows, and light configuration
• Excellent communication and facilitation skills across all levels – from PMs to VPs to superintendents
• Experience with construction tech, AI, field training, or document management is a plus
• We're especially excited about candidates with backgrounds in top‑tier consulting (e.g., McKinsey, BCG, Bain) or strategic roles at innovation‑forward general contractors. If you've helped enterprises implement complex technology, led digital transformation work streams, or partnered with field ops to drive behavioral change: this role offers a rare opportunity to go from advising to building. You'll take AI out of the boardroom and into real‑world jobsite workflows, driving measurable outcomes across one of the world's largest industries.

• Customer empathy:
  You care about…