Job Description: Engagement Manager

Salary: $100K - $200K Location Type: Remote Employment Type: Full-Time

Company Overview

At Trunk Tools, we are the leading AI company revolutionizing construction, the second-largest industry on Earth. We have recently secured a $40M Series B funding round led by Insight Partners, bringing our total funding to $70M from top-tier investors including Redpoint and Innovation Endeavors. This capital infusion 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 relies heavily on analog processes. Trunk Tools is changing this by embedding AI directly into field operations.

Founded by experienced builders and technologists from Stanford and MIT, our team has a proven track record of delivering software used by over 140,000 field professionals, impacting millions of users and contributing to over $10 billion in built projects. Many of us have direct field experience, providing us with a deep understanding of the industry's unique challenges.

After years of developing the "brain" of construction, we are now launching production-ready AI agents, beginning with intelligent document processing and Q&A, and rapidly expanding into core operational workflows. Our team has doubled in the past year, and with over 65 employees (including 25+ engineers), we are scaling rapidly and entering a period of hypergrowth. This presents a rare opportunity to join us at a pivotal inflection point.

Position Overview

As an Engagement Manager, you will serve as the primary partner for our customers, helping them implement AI workflows that drive lasting adoption and value. This is a high-touch, high-impact role focused on value delivery, behavioral change, and workflow transformation. You will guide customers in embedding AI into their daily operations, fostering not just trial but trust in our solutions. Engagement Managers are the crucial voice of the customer, responsible for uncovering explicit and implicit business needs and collaborating closely with our Product team to shape the future roadmap.

We are seeking a candidate who brings strategic thinking, exceptional executional rigor, and a strong sense of curiosity as we define the best practices for deploying enterprise AI in the built environment.

Responsibilities

• Customer Embedding:
  • Act as the day-to-day partner for strategic accounts.
  • Shadow customer workflows to understand operational realities.
  • Build trust and rapport with field teams and executive stakeholders.
  • Co-design impactful AI solutions tailored to customer needs.
• Workflow Design & Deployment:
  • Map and translate complex construction workflows into structured implementations.
  • Configure AI agents to meet specific project requirements.
  • Test data flows and ensure seamless integration.
  • Activate jobsite teams and drive initial adoption.
• Training & Enablement:
  • Develop comprehensive training curriculum.
  • Conduct live workshops and training sessions.
  • Certify customer "champions" to facilitate scaled adoption.
  • Drive executive-level understanding and buy-in for AI initiatives.
• Customer Advocacy:
  • Gather detailed qualitative and quantitative feedback from customers.
  • Synthesize insights and present actionable recommendations to Product and Engineering teams.
  • Ensure customer feedback directly influences roadmap development.
• Metrics & Reporting:
  • Define key adoption KPIs and success metrics.
  • Report on measurable impact, such as time saved and efficiency gains.
  • Track and communicate success across project milestones.
• Cross-functional Execution:
  • Coordinate effectively with Sales, Product, Engineering, and Customer Experience (CX) teams.
  • Ensure a seamless and positive customer journey.
  • Identify opportunities for upsell and expansion of services.

Qualifications

• Experience: 5+ years of combined experience in Construction AND Technology, with a focus on innovation, operations, or field deployment teams.
• Adoption & Change Management: Strong track record of driving technology adoption and managing behavioral change within complex organizational structures.
• Communication: Ability to work comfortably with both business and technical audiences, effectively translating field needs into product requirements and vice versa.
• Technical Aptitude: Possess technical curiosity and comfort working with cloud-based tools, APIs, LLM workflows, and light configuration.
• Facilitation Skills: Excellent communication and facilitation skills, effective across all levels of an organization, from Project Managers to VPs and Superintendents.
• Preferred Skills (Plus):
  • Experience with construction technology (ConTech).
  • Background in AI or machine learning applications.
  • Experience in field training or customer enablement.
  • Familiarity with document management systems.
• Ideal Candidates: We are especially interested in candidates with backgrounds in top-tier consulting firms (e.g., McKinsey, BCG, Bain) or those who have held strategic roles at innovation-forward general contractors. Experience in leading enterprise technology implementations, driving digital transformation workstreams, or partnering with field operations to achieve behavioral change is highly valued. This role offers a unique opportunity for individuals who have successfully navigated these areas.