Instructional Designer & Learning Operations Lead

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 100+ employees (50+ engineers), we’re scaling fast and entering a period of hypergrowth. This is a rare opportunity to join at an inflection point.

Position Overview

Trunk Tools is looking for an Instructional Designer and Learning Operations Lead to build and run the certification curriculum behind our AI-Enabled GC program. This is a shared Center of Excellence role — you’ll design once and configure for every account, not rebuild for each. You’ll own the full learning system: the curriculum design across business units and roles, the content itself, and the learning-management platform that delivers and tracks it. The heaviest lift comes early — content has to exist before the field can deploy, so authoring front-loads in Phase 0. We expect to start this function with two people during the build and settle to one plus contract support once the curriculum moves into maintenance. Travel is occasional, up to 15%.

Key Responsibilities

Curriculum & Instructional Design

Design certification tracks and modules segmented by business unit and role, progressing from foundational AI literacy to advanced, workflow-specific use.

Build for a blended model — video, quizzes, and in-person components — with assessments that make certification mean something.

Hold a clear standard for certification: trained, used in the workflow, and assessed.

Content Authoring & Production

Author and produce the learning content, and manage contract authors during peak build.

Front-load authoring in Phase 0 so the curriculum is ready before field deployment begins.

LMS & Learning Operations

Administer the learning-management system — enrollments, cohorts, certification tracking, and reporting.

Keep the operational engine running so cohorts move through on schedule.

Localization & Reuse

Build the curriculum once and configure it per GC, maintaining the shared curriculum map.

Balance what stays common across accounts against what must be tailored.

Maintenance & Refresh

Keep content current as AI tools and Trunk Tools products evolve — update and retire modules on a regular cycle.

Measurement

Track attendance, completion, certification, and assessment scores, and feed them into the program’s KPIs.

Qualifications

Experience

5+ years across instructional design / adult learning and learning operations / LMS administration.

Corporate training or enablement experience; technical enablement or AI/software training is a strong plus.

Experience standing up or running a certification program. Construction or AEC is a plus.

Skills & Knowledge

Instructional-design practice (e.g., ADDIE or SAM) and hands-on LMS administration (e.g., Docebo, Cornerstone, TalentLMS).

Content authoring tools (e.g., Articulate / Rise, Camtasia) and solid assessment design.

Able to run a content pipeline like a project — scope, schedule, and ship.

High personal AI fluency; you use the tools you’re teaching.

Education

Bachelor’s in instructional design, education, or a related field — or equivalent experience.

Instructional-design or LMS certifications are a plus.

What we offer

🎖️ A close-knit and collaborative early-stage startup environment where every voice is heard and every opinion matters

💰 Competitive salary and stock option equity packages

🏥 4 Medical Plans to choose from including 100% covered option. Plus Dental and Vision Insurance!

🤓 Learning & Growth stipend

🏠 Flexible long-term work options (remote and hybrid)

🥨 Free lunch provided in the office in NYC & Austin - you’ll never go hungry with us!

🛫 Unlimited PTO; We truly believe in work-life balance and that hard work should be balanced with time for rest and rejuvenation

🏝 IRL / In-Person retreats throughout the year

Please note: All official communication from Trunk Tools will come from an email address ending in @ trunk.tools . If you receive outreach from any other domain, please disregard it or report it to us.

At Trunk Tools, we’re working hard to build a more productive and safer environment within the construction industry, and we strive to live by these same values here at Trunk Tools HQ. 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.