Chief Technology Officer, Trunk Tools

• 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

Desirable

• 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
• 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