DASH 2026Join my session June 10 at 10:00 AM — Room 409, the Javits Center.See the talk

Helping engineering leaders make deliberate technology decisions and deliver them.

A small consulting practice for organizations that want their software and engineering teams to be a multiplier. Technology advisor and builder focused on AI adoption, engineering organization culture, and systems architecture.

Practice areas

01Leadership

Fractional CTO

Strategic technical leadership without the full-time overhead. Roadmap, architecture, hiring, and investor conversations at the right scope for your stage.

e.g., joining a Series A team for two days a week to lead the platform rebuild.

02AI strategy

AI Transformation

Not 'add a chatbox.' Restructuring how teams use AI across the SDLC and guiding where AI belongs in product. Real leverage, not just lines of code.

e.g., rebuilding a customer-success workflow so AI handles triage and humans do judgment.

03Org & process

Engineering Transformation

Org design, DORA, Team Topologies, onboarding systems, toil reduction. The conditions for a team to ship sustainably.

e.g., reshaping a 60-person org around stream-aligned teams without losing six months.

04Hands-on

Software Development

Hands-on builds for systems that matter. Marketplaces, platforms, distributed systems. With your team or independently.

e.g., shipping the v1 of a B2B marketplace from a blank repo to first dollar.

Matt Littlehale

I'm Matt Littlehale.

I've spent the last twenty years leading engineering teams.

I run M. Littlehale & Co. as a small, deliberate practice. That means I take on a handful of engagements at a time so I can be substantively useful to each one. Not a strategy deck author, an actual operator.

I occasionally write here: matt.computer. And I sell tshirts here.

Come see me speak at Datadog DASH on June 10th!