Tom Halpin · Technology Leader · Philadelphia
Leading technology. Loving wine. Always learning.
I'm Tom — a technology leader and founder of The Waitlist. I've led engineering and product teams as a VP, a Director, and a CTO — most recently at BottlePop.com and Wine Access — after a first career as a wine expert.
About
Technology was my second act. My first was wine — I spent years as a wine educator and expert behind the counter of wine shops, learning the trade bottle by bottle. In my thirties I went back to school for a bachelor's in technology at Villanova, then joined Wine Access in 2007 as one of its first employees.
Over the next several years I helped build the company through roughly 50x revenue growth, culminating in its sale to a private equity firm. The ownership transition that followed proved difficult, and in 2015 I came back to help get the technology organization back on track. At one point in 2018 I was the company's only technologist — running development, QA, and product single-handedly for the better part of a year — before rebuilding the team and rising to VP of Technology & Product.
I like problems where deep domain knowledge and good engineering meet. At Wine Access that meant a temperature-aware logistics program that protected wine in transit, an early LLM experiment (with Chicago Booth & YPO) that wrote marketing emails well enough to tie our human writers, and a recommendation engine that paired the right bottle to the right person. AWS invited me to present the work in their "A Perfect Pairing" webinar.
After Wine Access, I spent 2025 as fractional CTO of BottlePop.com, leading the tech team in building an MVP for a wine retail concept powered by influencer marketing. We shipped fast and learned faster — ultimately the product/market fit wasn't there, and the project wound down.
In 2026 I founded The Waitlist — a QR-code waitlist that texts people when it's their turn, no app to download. I'm still endlessly curious. I just spent a year in Wharton's executive CTO program, where a deep dive into product management reshaped how I think about a field I've worked in for over a decade. And I'm pushing my Southern Vietnamese from B1 toward fluency — classes plus self-study, 5+ hours a week. The throughline, in work and in the cellar: stay curious, taste everything.
Track record
What I care about
Technology
Leading pragmatic, durable engineering — AWS-native, product-minded, team-first.
Wine
Twenty years in the trade and a serious cellar. Always hunting the next pour worth remembering.
Learning
Endlessly curious — fresh off a year-long Wharton CTO program, working daily toward fluency in Southern Vietnamese (B1).
Recent Work
I spent one too many afternoons idling in the car line at my kids' school, watching a clipboard-and-walkie-talkie operation shout names into the wind. So I built thewaitlist.com — a QR-code waitlist where you join a line from your phone and get one text when it's your turn. The software took a weekend; getting America's phone carriers to let me send that text took an LLC, an EIN, and five rejections in three weeks.
Read the write-up →My kids — eight and ten — eat breakfast under the kitchen TV, and I wanted that screen to earn its keep. So I built a single web page that deals out one big fact at a time: 227 cards of vocabulary, artists with rotating paintings, the thirty biggest countries with maps, and counting to one hundred in Mandarin with native audio. It reshuffles itself every morning and won't repeat a card within a breakfast.
Read the write-up →Experience
Education & recognition
A year-long "mini MBA" in technology leadership, completed 2026 — eighteen core modules across technology strategy, emerging tech, and execution, plus three six-week electives (including a deep dive into product management) and live sessions on generative & agentic AI, taught by Wharton faculty.
Reading & writing ahead of listening; classes plus self-study, 5+ hours a week toward the next level
"A Perfect Pairing": scaling Wine Access 400% and cutting costs 50% with ML on AWS — watch the recording (18 min)