Product Leader / Operator / AI Builder

I build AI products and systems for complex operations.

14 years building products at the intersection of operations, scale, and ambiguity — from a $4.4B ed-tech unicorn to a disaster platform serving 18M users. Former CIA Officer. J.D. Most comfortable working close to leadership on hard problems.

Matt Hubbard outdoors in Boulder, Colorado
Experience

Experience across product, operations, AI, and regulated domains.

High-Growth Product

14 years across startup product and operations

From scaling a marketplace to hundreds of partners at a $4.4B unicorn, to building Watch Duty's flooding expansion for 18M users, to growing a B2C app from 2,000 to 500,000 accounts.

CIA / Emergency Ops

Former CIA officer. Active EOC volunteer.

Former CIA, Disaster Tracking PM. Direct counterterrorism experience working alongside special forces in war zones. Active EOC Situational Awareness Volunteer. Former Principal at Watch Duty.

Scaling Systems

Built operating models through growth stages

Redesigned models to deliver Guild academic implementations 3x faster. Scaled supply-side from a small squad to a cross-functional department of six PMs, with no custom engineering per partner.

Applied AI Systems

From support tooling to agent workflows

Built GenAI-powered SMS support that outperformed all other channels in responses and conversion. Now building AI products, reusable skills, and agent operating systems.

Portfolio

Selected work that shows how I think and build.

Outpost

Alpha v0.1-alpha

An AI-powered headless intel analyst for executives, operators and consultants, including source synthesis, insights, signals, and red team analysis.

Agent OS

Public repo v1

A public operating layer for AI agent collaboration: roles, skills, project conventions, and memory patterns.

AI Skills

Public repo v1

A public skill library for AI-assisted judgment, learning, execution, and review.

Work With Me

For operators and founders working through ambiguous, high-leverage problems.

Open to focused advisory, project sprints, and fractional work where the problem sits at the intersection of strategy, execution, and AI-enabled systems.

Product

Shape ambiguous product bets

Turn unclear ideas into scoped plans, sequencing, and decisions teams can act on.

AI Workflows

Build practical systems for AI-assisted work

Fit tools and workflows to real team behavior and maintenance constraints.

Strategy

Reason through complex plans

Refine positioning, systems, roadmap, and order of operations when the answer is not obvious.

Start lightweight

Send the context first.

If one of these problems maps to something you are working through, send me a note on LinkedIn with the context and what kind of help you are considering.

Message on LinkedIn
Writing

Recent writing, published elsewhere first.

Essays and field notes on AI-assisted work, operating systems, product judgment, and career transitions. Published on Substack and surfaced here.

Jan 3, 2026

Write Better AI Preferences, Not Prompts

Some people try to prompt better. The faster method is to set preferences once, so every conversation starts with your preferred instructions and context.

Contact

How to reach me.

Open to Chief of Staff, operations, and strategy roles where operational complexity and AI systems are part of the work. Also open to focused advisory conversations.