Shelterwood AI Inc. · Toronto, Canada
A portfolio of well-crafted software.
Shelterwood AI builds and runs a portfolio of small software businesses. We start from the problem, not the technology, and add to the portfolio as new ideas earn their place. Cuesheet is the first.
What we do
We design, build, and operate our own software businesses. Each one is built AI-native from the ground up: the intelligence is part of the foundation, not a feature bolted on at the end. The result is software that does more of the tedious work for you and stays out of the way of the rest.
Our approach is deliberate. We would rather hold a few products made well than a long list of half-finished ones, and we judge our work by whether the people who use it get more done, with less effort, than they did before. The portfolio is meant to grow — but only as fast as we can build to that standard.
Our flagship: Cuesheet
Cuesheet is a co-instructor for indoor-cycling and spin classes — delightfully simple to build a class, and effortless to run from the bike. Plan the ride in advance, line each block up with the music, and let Cuesheet cue the class so you can teach instead of watch the clock. It is built for iPhone and iPad.
Cuesheet is the first business in the portfolio, and the model for how we build the rest: a real tool for real people, made well.
How we build
Shelterwood runs on an AI-native operating model. Most of the building and day-to-day work is done by an AI system we call Silas. People set the direction and hold the decisions that should stay with people — money, anything hard to undo, and matters of judgement. Silas does the work up to those lines and brings the decision back to a person.
It is early, and the model is still being proven. We are starting with one product and letting the approach earn its keep. More about how we build →
Why "Shelterwood"?
In forestry, a shelterwood is a stand of mature trees left in place to protect the next generation of growth until the seedlings are strong enough to stand on their own. The name reflects how we work: stewardship over speed, patience over hype, and craft that compounds over time.