Your league's caddie,
always on call.

Golf league members & administrators

Sir Winston AI is for members of participating golf leagues in Canada and North America. Members are registered by their league administrator — the service is not open to the general public.

League administrators use Winston to manage tee times, availability, and weekly updates. Members interact with it via WhatsApp to query standings, scores, and league info.

Simple, league-first workflow

1. Leagues register members. A league administrator onboards members and obtains their consent before any messages are sent.
2. Members interact via WhatsApp. Members send commands like !teetimes, !standings, or plain questions to get instant league information.
3. Updates delivered automatically. After each round, standings, rankings, skins results, and highlights are pushed to all league members.

Opt-in and opt-out

Sir Winston AI only messages golf league members who have been invited or registered by a participating league administrator with their prior consent. We do not send unsolicited messages or marketing communications of any kind.

Messages are limited to league operations: tee times, availability, standings, rankings, skins results, and scorecard highlights.

Your data is used only for league operations

We collect your WhatsApp phone number and message interactions solely to operate the league service. Basic data such as your name, phone number, league participation, and scores may be stored to deliver league updates. We do not use your data for advertising or sell it to third parties.

You may request deletion of your data at any time. Request data deletion →

Read our full Privacy Policy →

Business information

Operator

Matthew Van Wely

Service

Sir Winston AI

Support

support@sirwinstonai.com

Website

sirwinstonai.com

Audience

Golf leagues — Canada & North America

Messaging

League operations only — no unsolicited marketing