Chief Technology Officer / VP of Engineering

Salary: $270K - $350K Employment Type: Full-Time

Position Overview

At Trunk Tools, we are the leading AI company revolutionizing the construction industry, 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 organization through this next stage of growth. You’ll partner with the CEO and executive 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 organization.
• 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 with 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 AI solutions.