AI fails at the wiring, not the model.
Most of what I've shipped sits at that seam: connecting a chatbot, a help centre or an agent to the systems that hold the answer, then making the result hold up for real users. Seven years on Upwork's support platform, the last three as Engineering Lead, and now my own builds at Adommo.
Results below are quoted from public sources where they exist, and labelled when they don't. Work at Upwork was team work; each case study says what my part was.
Upwork · Dec 2021 – Jul 2024
I engineered the Forethought–Zendesk integration behind the 58% chatbot resolution rate Zendesk published in its Upwork customer story, then owned the platform through 2024.
Upwork · May 2022 – Sep 2022
Zendesk only knew who an Upwork user was from tags pushed at login. I replaced them with real-time GraphQL data and retired the job that made them.
Adommo LLC · Mar 2026 – Present
A retrieval-augmented support assistant that answers from a team's own help centre and ticket history, and opens a Zendesk ticket with the context attached when it can't. In development.
Upwork · 2020 – Mar 2021
Disputes involved a client, a freelancer and an agent in separate conversations. Using special access to Zendesk's side-conversation API, we put all of them in one ticket.
Upwork · Feb 2020 – Apr 2020
Zendesk Guide only knew a user as they were at login. I led the team that built a JavaScript OAuth 2.0 client so the Help Center could read live account data from the Upwork API.
Upwork · Jun 2017 – Jul 2024
Upwork's Help Center is the self-service front door to a 300+ agent support operation. I built the theme framework that carried eight redesigns, then led the team that owned it.
Upwork · Jun 2017 – Dec 2021
Upwork's first support chatbot. I integrated Ada with Zendesk, built a wrapper so any team could embed it, and added routing data so live-chat handoffs reached the right agent group.
Adommo LLC · Jun 2026 – Present
Guide theme imports fail late, after upload. Zendesk Skills lints themes locally, deploys them through the Themes API, and gives AI coding agents the conventions they're missing.
Adommo LLC · Jun 2026 – Present
Each AI coding tool keeps skills in its own place, so copies drift. Sync Skills links one canonical source into 16 tools and audits every target.
Adommo LLC · Jun 2026 – Present
Three agent skills: architecture drift checks before code changes, friction logging, and a weekly review that turns the log into new skills.
Upwork · 2020 – Jul 2024
Agents kept leaving the ticket to look things up. Sidebar apps and Agent Workspace integrations brought that context into a single ticket view.
Upwork · Apr 2020
Upwork's $1M COVID-19 talent grant program needed an application platform and a review process, fast. I led the development team that built it in a week.