System Online
Location NYC Metro
Status Seeking
Role Dir / VP Engineering

// Engineering Leader //

JERÓNIMO COLÓN III.

// Fifteen Years Building Teams & Products

// Management Profile Stats
Experience 15 YRS
Companies 7+
Teams Led 12+
Uptime 99.9%
Availability Open
[ 01 ] Profile.dat

Fifteen years, a lot of ground covered.

Jerónimo Colón III
IMG_JC3 · ON FILE

My career has spanned financial data services at Lazard and Thomson Reuters, civic technology at Case Commons, consumer SaaS at SinglePlatform, and most recently Tripadvisor, where I led two different product areas across two chapters of my career there.

First, I led two teams on the Restaurants side, where we built and shipped Menu Connect, a syndication platform connecting restaurants to 100+ distribution partners. Then I moved to Experiences, where I led four teams building and scaling Tripadvisor's tours and activities marketplace (think things to do when you arrive at your destination).

What's stayed constant across all of it is how I think about leadership. I'm not a delegator who manages from a distance. I build relationships with the people on my teams, learn what they're trying to grow toward, and create the conditions where that growth can happen. I believe engineers do their best work when they understand the "why" behind what they're building and feel genuine ownership over it.

While still very important, the measure I care most about isn't velocity or uptime. It's whether the people on my teams actually look forward to Monday. An engaged engineer outperforms a disengaged one in every dimension, and fostering that environment is the work I find most meaningful.

I came to software through biology, and that background still shapes how I think: systems, feedback loops, emergent behavior, the gap between what a model predicts and what actually happens. I find that framing useful in engineering organizations.

[ 02 ] On AI

Yes, I'm one of "those people" now.

I'll be honest: I'm having more fun building software right now than I have in years, and AI is mostly the reason why. The distance between "huh, I wonder if…" and a thing actually running on my screen has basically collapsed. For someone who never quite stopped being the kid who wanted to take everything apart to see how it worked, that's catnip.

I don't buy the doom, and I don't completely buy the hype. AI is a wildly capable, occasionally overconfident collaborator - a bit like pairing with a brilliant junior engineer who has read the entire internet and will, given the chance, make up facts with total conviction. So I keep a hand on the wheel and, like a good mentor, I start with a robust plan. I give it room to cook, but I read everything it hands me. The subtle secret is structure - again, creating a robust plan upfront and a self-improving feedback loop.

Mostly, I try whatever crazy ideas that pops into my head - and I do mean every-single-one. I've gone far enough down the meta-rabbit hole that I started building tools to test the tools, and a custom framework for a fully automated, self-improving/self-correcting agent - like totally hands free.

Is it going to change everything? Probably. Am I going to fret about that, or keep building weird and quirky little projects with it and enjoy myself? …Both. Obviously both.

[ 03 ] Current Mission

Active objectives.

Currently seeking a return to a Director or VP of Engineering role, with a preference for mission-driven organizations working on problems that matter, because I'm driven by the impact I can make.

For funsies, I got my hands dirty again coding a little passion project, building a digital board game. It has been genuinely so much fun! No roadmaps, no stakeholders, no PRDs. Just me, a problem, and modern tooling.

Naturally, one project became several (and it hasn't stopped). That digital board game finally has a name: Tapas Bar, a browser-based drafting game with a twist, a healthy dose of take that, and lots of laughs. Call it my tapas-themed love letter to Sushi Roll.

The rest are what happens when you're enjoying the tooling a little too much. There's an eval harness that measures whether changes to AI system directives actually shift model behavior, scored with blind-judged trap prompts (evidence over vibes). There's claude-constitution, a reusable template that stamps the same engineering discipline onto every new project I start. There's that automated self-learning framework I hinted at above, where AI agents self-optimize and self-improve across a number of cohorts. And there's an irrigation planner, because apparently I can't look at a backyard without wanting to optimize it.

[ 04 ] Personal Data

Off the clock.

Married, two kids, and a furbaby (who has strong opinions about my work schedule 🐶).

Night owl by nature, which has served me well across time zones and production incidents alike. When I'm not thinking about engineering teams or gaming logic, I'm usually in the weeds of some home networking rabbit hole. The kind that starts with "I should improve my Wi-Fi 7 (6Ghz) coverage" and ends with VLANs for everything (APs, IoT, security devices), dual WAN failover, dedicated switches, and more APs than a home should have, but hey, at least I have amazing coverage. 😉

Away from my computer, I'm into many things (too many). I'd like to think myself a Renaissance Man, but I'm more a Jack of All Trades. I enjoy sci-fi, action and adventure across every format: books, movies, and TV shows. And I'm a longtime dabbler in photography, art, and screenwriting. I also enjoy home improvement and I'm obsessed with car detailing.

// Transmission

"Life's short, live it to the fullest while leaving the world better than you found it."

- JC3