I help engineering leaders navigate the hardest problems in scaling technology organizations. I’ve built and led engineering teams through two exits — Weedmaps (IPO) and ShopKeep ($550M acquisition) — scaling from early-stage to hundreds of engineers. Most recently I served as CTO at BuildOps.
How I Work
CTO & Engineering Leadership Mentoring
One-on-one advisory for CTOs, VPs of Engineering, and technical co-founders navigating the challenges of scaling — organizational design, hiring, culture, and the transition from builder to leader. Available through Plato, Intro.co, or direct engagement.
Fractional Technical Leadership
Hands-on technical leadership for companies between CTOs or scaling through inflection points. I embed with your team to set technical direction, unblock execution, and build the engineering culture that outlasts my engagement.
AI Strategy & Implementation
Practical guidance on integrating AI into products and engineering workflows. Not theoretical — grounded in building real AI-powered products and leading teams through the transition. I help leaders cut through the hype and make decisions that compound.
Who I Work With
Founders preparing for their first VP of Engineering hire. CTOs navigating post-Series B scaling. PE-backed companies needing technical diligence or interim leadership. Investors seeking technical assessment of portfolio companies. If you’re facing a decision that will shape your engineering organization for the next 2–3 years, that’s where I focus.
Background
- CTO, BuildOps
- Led engineering and AI strategy for vertical SaaS platform serving commercial contractors
- CTO, Weedmaps
- Scaled engineering from 30 to 300+ engineers through IPO (MAPS, NASDAQ)
- VP Engineering → CTO, ShopKeep
- Built and led engineering through $550M acquisition by Lightspeed Commerce
- Writing
- itsmeduncan.com — on engineering leadership, AI, and building technology teams
- Based in
- Southern California
Get in Touch
The best way to start a conversation is email. No forms, no scheduling links — just tell me what you’re working on.