I Let Claude Run My Hockey Team. Here is the progress.
I’m a hockey team captain. Not the inspirational speech kind — the administrative kind.
Every season, I have to get about 20 players setup for a the Mahogany Woodsmen in ROHL out at Power Play Rinks in Exton. This is a job nobody wants. Every single season it is the same grind: emails, tracking, cost calculations, payment collection, roster wrangling.
It’s not hard. It’s just constant. Dozens of small actions spread over three or four weeks.
This spring I handed it to Claude. Not as a demo. As a real experiment.
The Setup
I’ve written before about how I learn technology — I don’t study, I play. So I needed something real to play with.
I gave Claude Code access to five years of my hockey emails. Not summaries — actual threads. Recruiting pitches, cost breakdowns, “hey are you in or out” follow-ups, payment chasers. I wanted it to understand not just what the process is, but how I do it. The tone I use. The cadence. Who gets a nudge and who doesn’t.
Then I asked it to take over.
What It’s Actually Doing
Claude sent the Welcome Back email for Spring/Summer 2026. It wrote it in my voice, got the tone right, and sent it to the team. I reviewed it first — but didn’t changed a word. It even included my lame joke about off season training (there is no off-season).
Every four hours claude wakes up on a schedule, it checks my inbox for replies. When a player responds — I’m in, going part-time, I’m out this year — it reads that, figures out what it means, and updates the Google Sheet automatically. No copy-paste. No manual entry.
Once the roster locks, it will run the cost formula. (It’s not just fee divided by players — there’s an early payment discount, a defending champions discount if we win championship for the winter season, the BenchApp fee, the team bank balance. It knows all of this.) Then it’ll send the payment email with the Venmo breakdown and start tracking who’s paid via email notification from Venmo.
I am hoping it will also track down USA-Hockey registration and put the sheet together for the rink when that time comes.
The full pre-season workflow. Running on its own.
What I Actually Learned
I am always trying to figure out how to use AI to solve problems. Solving a low risk problem allows me to take bigger risks, that I can recover from easily. (it is just my team - and as a human I mess up this process all the time.)
Old model: I make every decision and take every action. I build spreadsheets - set the schedule, track down stragglers, pay the bill and administer everything.
New model: I define the process and the intent. Claude examined the history - proposed a process that I reviewed and approved. I stay in the loop for the judgment calls — the player who needs a real conversation, the pricing edge case, the “should we recruit this guy” question. All the administration - That runs without me.
Five years of emails gave Claude enough context that it didn’t just know the what — it understood the why. It knows I target around 17 players. It knows I value a reliable sub pool. That accumulated pattern is now something it can act on.
Honest Assessment
I’m watching it closely. I still see every email. I still have eyes on the sheet. If it misreads a reply I’ll catch it.
But so far? It’s working. The emails sound like me. The roster is filling in. The process is moving forward without me pushing it.
Season starts April 19th. I’ll let you know how it goes.