Chief Technology Officer

At Trunk Tools, we’re the leading AI company revolutionizing construction—the second-largest industry on earth. With deep traction among Fortune 500 general contractors, we have raised $30M from top investors including Redpoint and Innovation Endeavors.

Our mission is to build the future of construction through intelligent automation. Construction is a $13+ trillion industry still operating primarily in analog—and we’re changing that by embedding AI directly into the jobsite.

Founded by builders and technologists (Stanford, MIT), our experienced team has delivered software used by 140,000+ field professionals, impacting millions of users and contributing to $10B+ in built projects. We're deeply rooted in construction, with many of our team coming from the field.

After years of developing the “brain” of construction, we are now deploying AI agents and workflows to automate critical tasks—beginning with intelligent document processing, Q&A capabilities and rapidly expanding across operational processes. We currently have 50+ employees, including 20 engineers, and have doubled our size in the last 12 months. We’re continuing to grow rapidly as we launch and scale multiple AI agents this year.

As Chief Technology Officer / VP of Engineering, you’ll own the technical vision and lead our engineering org through this next stage of growth. You’ll partner with the CEO and exec team to shape product direction, build high-performing systems and teams, and ensure speed, reliability, and scalability as we grow our platform and AI agent ecosystem.

This is a rare opportunity to own and build the core technology behind a mission-driven, AI-native, Series A+ company reshaping the world’s second largest industry.

Key Responsibilities

• Define and drive the technical vision, strategy, and architecture aligned with Trunk Tools’ product and business goals.

• Be a key member of the executive team, contributing to company-wide strategic planning and priorities.

• Evaluate and implement emerging technologies, especially around AI/ML, automation, and scalable infrastructure, and continuously evaluate when to build, buy, or partner to accelerate the roadmap.

• Build and foster a high-performing, inclusive engineering culture with a strong bias for action, while also partnering with Talent to craft our engineering brand and close top candidates

• Mentor technical leaders and create clear career growth paths across the org.

• Own the technical roadmap, balancing speed of delivery with long-term platform health and security.

• Align engineering execution with company goals around velocity, reliability, and user impact with a high degree of predictability and accountability.

• Collaborate cross-functionally with Product, Design, CX, and GTM teams to deliver seamless user experiences.

• Set and manage the engineering budget, including cloud costs and external vendors / contractors.

• Build and manage best-in-class security, privacy, and compliance teams and practices appropriate for the enterprise.

Must-Have Qualifications

• Proven experience as a CTO, VP Engineering, or equivalent leadership role in a fast-paced, high-growth B2B startup. Ideally someone who has scaled an engineering team from ~25 to 75+ while balancing speed, quality, and team health.

• Strong technical depth across software engineering and infrastructure (AI/ML exposure a plus).

• Demonstrated success scaling distributed teams, systems, and development processes.

• Strategic mindset with the ability to connect engineering decisions to business outcomes and present at board meetings or similar.

• Excellent communication skills and comfort working with technical and non-technical stakeholders alike.

• Alignment to our core values of High Output, Low Ego, and No BS.

Preferred Qualifications

• Experience working in or with industries like construction, field services, or fragmented / document-intensive verticals.

• Previous experience leading AI-first product development or deploying intelligent automation tools.

• A passion for building products that empower underserved workforces.

What we offer

• 🎖️ A close-knit and collaborative hyper growth startup environment where every voice is heard and every opinion matters

• 💰 Competitive salary and stock option equity packages

• 🏥 3 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)

• 💰 401K

• 🥨 Free lunch provided in the office in NYC and 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.

We realize applying for jobs can feel daunting at times. We don’t expect you to check all the qualification boxes and encourage you to apply if you have experience in some of the areas.

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.