Senior product and operating partner — former Google executive (2024–2025). Hired to operationalize a portfolio of ventures around the principal's cognitive style. The work was diagnosis-heavy: figuring out which projects had real signal, which were drains, where their time created the most leverage. Designed lightweight operating systems that worked with their attention patterns rather than against them — including AI-assisted workflows tuned to the principal's working style. Part product judgment, part executive partnership.
Chris Gueits
("Gates")
AI-native operator helping companies make the transition.
Remote·Miami-based·Available 10–25 hrs/week
Positioning
I work with founders and senior leaders making their company AI-native — adopting the tools, redesigning the workflows, integrating AI into the product, or building something that wouldn't have been possible eighteen months ago.
The bottleneck isn't the technology. It's judgment. Where AI actually changes the work versus where it adds noise. What to automate, what to leave human, what to build, what to buy. Which experiments deserve to scale and which are dressed-up demos. AI gives you a water cannon. Most problems need a pressure cleaner.
That's the work I do. Senior product brain, four-time founder, builder who ships in days rather than quarters. I run my own experiments — most recently a padel matching app, a sleep diagnostic, a relationship app, and the page you're reading — so the advice I give clients is the advice I've already used on myself.
What I'm hired to do
Engagement shapes specific to AI-transition work.
AI integration roadmap. Walking the team through their actual workflows, identifying where AI changes the economics, sequencing the rollout. Less buzzword, more discrimination.
AI-native product design. Sitting with a founder building a product where AI is the substrate, not the feature. User research, prioritization, the questions nobody's asking yet because the category is too new.
Build-versus-buy judgment. Which AI tools belong in the stack, which need to be built, which are noise. The market is moving weekly; this work has a real shelf life.
GTM design for AI-native products. Translating a working AI product into a real go-to-market motion. Positioning into a category that doesn't yet exist, pricing into willingness-to-pay that hasn't formed, distribution into channels being reinvented in real time.
Senior partner to a founder navigating the transition. Weekly cadence. Roadmap discipline, the hard conversations about what's working and what's theater. For founders who feel the velocity but want a peer who can tell signal from hype.
If your situation doesn't quite match one of these, send a brief anyway. AI-native work is novel by definition — most engagements I take don't fit a prior template.
Recent work
Strategic GTM consultant — Airbnb (2015). One of a small external team of operators brought in to solve an intractable supply-side problem. Worked independently to design a new acquisition methodology, finished top of team in results, and was asked to train the rest of the cohort in the protocol — which was later templated and scaled globally to address supply challenges in other markets.
Founder & CEO — Rison (2018–2023). Built a virtual group coaching product from zero. Pivoted from in-person retreats to a digital subscription with $2,193 LTV and 4.7/5 satisfaction across 500+ sessions. Average customer lifespan 19 months — six times the industry average. Owned product, growth, and the mission-driven culture that made retention possible.
Product strategy — Mobile Accord (2012). Onboarding redesign drove 304% growth in active users. Activation campaign work drove 307% growth in core engagement metrics. Identified strategic partnerships that cut $2M project opex by 67%. The kind of unglamorous product judgment that compounds.
Founder & Chairman — Roots of Hope (2003–2013). Built a national community of 900+ leaders across 99 universities — remote-first and distributed before either was a category. Led a team of volunteer leaders without formal authority, designed programming featuring former heads of state, and shaped a movement that ran for a decade.
Independent builds
Two projects that show the shape of how I work outside of paid engagements.
A padel matching app (2026). Live SMS product I built solo as a non-developer through a two-tool AI workflow (Claude for strategy and architecture, Claude Code for surgical edits and deploys). Webhook routing, scheduled cloud functions, payment ingestion, tiered messaging by user behavior. Two-month progressive build. Real users, real revenue, no engineering co-founder. The transferable practice isn't "I used AI to write code" — it's the operating system around it: structured living docs designed for AI cold-starts, codebase rules that prevent recurring failure modes, dry-run gates before anything irreversible, and a clean separation between what humans decide and what the agent executes. The four bad weeks every team burns figuring this out, already paid.
A site for ESPN soccer writer Ryan O'Hanlon (2026). A site for ESPN soccer writer Ryan O'Hanlon. Cold-pitched, shipped before any contact. AI built the code; the work was direction. The blurry homepage photo seemed random but suggested more. His dog (whom he calls his "personal ombudsman") and the Packers banner weren't footnotes, they were clues. The retro-coded Substack logo and the 80s-hairstyle Twitter banner read as a specific aesthetic register: counter-culture sensibility under a professional surface. The model couldn't see any of it. Mining Substack comments to find what his readers had been asking him to build. Catching the first-pass design's color system as wrong (black-and-yellow Steelers) and steering it to forest green and gold (Packers colors). Pausing for previews twice before any full build. Cutting sections that overproduced. Shipped in under 24 hours. The transferable practice: knowing what to leave in, what to leave out, and when to make the AI stop.
Stack across recent builds: Cursor, Claude Code, Firebase, Twilio, Netlify.
Background
Princeton — History, certificate in Spanish. McGraw Scholarship. 100-page senior thesis. Varsity football, 2006 Ivy League Champions, four-year letter winner, Special Teams Captain.
Tuck School of Business at Dartmouth — Business Bridge Program (intensive MBA curriculum).
Teach For America — bilingual classroom teacher and district data manager, Los Angeles. Synthesized district performance data into board-level reports.
Native fluency in Spanish. Significant professional experience in Latin America.
Four-time founder across non-profit, consumer wellness, consumer mobile, and consulting.
How I work
Five things I commit to in every engagement.
Direct user contact in week one. I don't form opinions from secondhand reports. I speak directly with the people whose behavior we're trying to understand.
Diagnosis before prescription. Most product problems are misdiagnosed. The first deliverable is usually a clearer problem statement than the one I was hired against.
Ship the smallest real thing first. Working software, even ugly, beats decks. Especially in AI-native work, where the gap between idea and prototype is now hours.
Make the team better, not make myself necessary. Fractional engagements work when the team gets sharper. I leave behind operating systems, not dependencies.
Transparent on what I don't know. I don't fake adjacent expertise. When something's outside my range, I say so and help find the right person.
Fit
Good fit if:
- Pre-Seed through Series B, up to roughly 80 people
- Founder-CEO or senior leader who wants a peer in the room, not a vendor
- Remote-first, comfortable with async
- Open to a senior outsider having real access in week one
- Building a product, redesigning a GTM motion, or navigating an AI transition
Not a fit if:
- You need full-time or on-site presence beyond occasional travel
- Procurement cycle longer than the engagement itself
- Looking for staff augmentation or pure execution capacity
- Looking for a coach or therapist; that's a different door on this site
The longer story
I grew up in Miami, the kind of Cuban kid who started his first business at fifteen because his family couldn't afford the football camps that would get him recruited. That hustle worked. Princeton. Ivy League championship. The American Dream.
What the resume doesn't show is the break.
A few days before I turned thirty, the company I'd built and the relationship I'd been in both ended in the same week. I spent a day at rock bottom, watching myself from somewhere outside my body, asking the only honest question I had left: how did I get here?
What I learned in the years after that has shaped every venture and every engagement since. Outcomes are not in your control. Your relationship to your own thinking is. A process orientation is. The work in front of you, done well, is the only thing you actually own.
The best operators I know — the ones who stay sharp through hard cycles — are not the ones with the most frameworks. They're the ones who know themselves well enough to think clearly under pressure, and disciplined enough to keep showing up to the work when the outcome is uncertain.
I bring that to the work. Strategic clarity and emotional steadiness are not separate skills. They're the same skill in different lighting.
If any of this resonates, the door is open.