Advising

I occasionally work with founders, CTOs, and engineering leaders who are navigating periods of growth, change, or uncertainty.

I’m not a full-time consultant, but I’ve led engineering orgs through hypergrowth, platform transitions, and major reliability efforts. Sometimes, a short conversation or a few hours of structured support can clarify the path forward.

Areas I can help with:

• Designing or evolving engineering org structures
• Managing through growth, reorgs, or platform transitions
• Coaching new or emerging engineering leaders
• Establishing ownership, reliability, and team health practices
• Improving incident response and escalation processes
• Making technical vision tangible without over-engineering
• Improving how your team handles incidents, from detection to postmortems
• Aligning incident processes with team structure, on-call, and long-term reliability goals

Background

I’m currently a Principal Engineer at North. Previously, I was a Senior Director of Engineering at Recharge, and before that, an early engineering leader at TaxJar, where I helped scale the platform and team prior to its acquisition by Stripe. I’ve also co-founded and operated Limited Run since 2009, and I’m currently building Looping, a tool for managing the evolution of software.

How it works

If you’re interested in working together, we’ll start with a short (free) 30-minute call to talk through your current challenges and see if it’s a good fit. If it is, we’ll figure out a lightweight way to move forward—whether that’s a one-time session, async feedback, or ongoing support.

Reach out

If you think I might be helpful, I’d love to hear from you.

You can email me at tom@sleepingpotato.com or connect on LinkedIn.