Winston Diaz

Senior Product Manager · AI Product Leader

Building applied AI tooling for over a decade, from machine translation to LLM agents, at global scale.

13+
years in product & localization
40+
countries launched
100+
markets served
20+
translation models trained
17
languages shipped
20+
AI apps & agents built

About

I'm a product management leader who's been working with machine learning since before it was mainstream, starting in localization. I spent a few years training custom translation models on Microsoft Translator Hub when the technology was still pretty limited, then joined the early beta of Google's AutoML Translation at Alarm.com and built a pipeline of language models across 40 countries and 17 languages. At Okcoin I did it again in a more mature form, an internationalization pipeline with AutoML that handled 80% of content across 100+ markets.  These days I run an AI and automation consulting and advisory practice where I'm hands-on building agents and apps, and lately I've been deep in agentic orchestration and applied agentic LLMs.

A decade of applied AI

One thread runs through all of it, from machine translation to agents. Select a moment to explore it.

Handybots · 2023 – now

Orchestrating a fleet of agentic apps

Now I run an AI and automation practice building and orchestrating a fleet of agentic apps: conversational support agents, an autonomous UI-testing agent that reasons with computer vision, a multi-LLM content pipeline, and a product-management cockpit that distills what every build teaches into standards the whole fleet shares. The throughline is orchestration: getting multiple agents and apps to compound on each other instead of working in isolation.

20+AI apps & agents built

  • LLM agents
  • Multi-agent orchestration
  • Fleet-wide standards
  • RAG

Selected work

Building

Things I've built and maintain hands-on, along with Dev contractors for SMB clients and Orgs.

Recommendations

"Winston played a critical role in our expansion into over 50 countries. He holds himself to high standards, always acts with the utmost integrity, and is a pleasure to work with."

Reed Grothe, SVP Global Business Development, Alarm.com

"Winston fine-tuned our organizational procedures and brought project management and quality-assurance discipline to day-to-day operations. A dedicated professional with a real interest in solving problems for the company and its clients."

Silvia Villacampa, Office Manager, Liberty Language Services

Skills & credentials

  • AI Product Management
  • LLMs
  • Agentic AI
  • Machine Translation
  • Localization / i18n
  • RAG
  • Prompt Engineering
  • Python
  • SQL

MIT xPRO · Product School (AI Product) · Wharton Online (Private Equity) · MBA, ENEB