Chief Technology Officer

Summary

Join Trunk Tools, a leading AI company revolutionizing the construction industry, as their Chief Technology Officer/VP of Engineering. You will own the technical vision and lead the engineering organization through its next stage of growth. Partner with the CEO and executive team to shape product direction, build high-performing systems and teams, and ensure speed, reliability, and scalability. This role offers a unique opportunity to build core technology for a mission-driven, AI-native company. You will define and drive the technical vision, strategy, and architecture, while also building and fostering a high-performing engineering culture. The ideal candidate will have proven experience scaling engineering teams in a fast-paced, high-growth B2B startup.

Requirements

• 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

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

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

Benefits

• 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