Shelterwood AI Inc. is a software company based in Toronto, Canada. We build AI-native software products — tools designed from the start around modern artificial intelligence, made to solve real problems for the people who use them every day.
What we believe
Good software earns its place. It removes friction, does the dull work, and otherwise stays out of the way. We think the best use of artificial intelligence is not to dazzle but to quietly handle the parts of a job that people would rather not do themselves.
So we build deliberately. We prefer a small number of well-made products to a long list of unfinished ones, and we judge our work by a simple test: do the people who use it get more done, with less effort, than they did before?
How we work
We build a portfolio of small software businesses, and run them on an AI-native operating model: an AI system named Silas does most of the building and day-to-day work, while people set the direction and hold the decisions that matter. The intelligence is part of the foundation, not a feature added late. You can read more on our approach page.
We design, build, and operate our own businesses end to end. The first is Cuesheet, a co-instructor for indoor-cycling classes.
Why “Shelterwood”?
In forestry, a shelterwood is a stand of mature trees left standing to shelter the next generation of growth. The old canopy protects the new seedlings until they are strong enough to thrive on their own.
The name captures how we want to work: with patience, stewardship, and an eye on the long term. We are building for durability, not for the next quarter.
The founder
Shelterwood was founded by Peter Cresswell, a professional engineer (P.Eng) trained at the University of Waterloo. He has spent more than fifteen years in healthcare technology and electronic medical records — building systems that clinicians and patients depend on. He was most recently VP of Technology at DoctorCare, which was acquired by WELL Health. Shelterwood is the next step in that work: an independent company building a portfolio of AI-native software of his own.
Where we are
Shelterwood AI Inc. is incorporated in Canada and based in Toronto, Ontario. You can reach us through our contact page.