Jill Stapleton

CEO and founder of 321 Oak.

I spent a long career in enterprise technology solutions and SaaS implementations. Now I run a small studio that builds calm, careful tools for everyday life. Away from the screen you'll find me on a trail, in a kayak or on a boat, usually with a plant or two not far behind.

View my LinkedIn My resume and career history live there.
Jill smiling at a stone lookout high above forested islands, with two children beside her.

What I'm building

Software that leaves your day a little better.

I run 321 Oak, a studio that believes tools should feel considered, calm and clear. Checked Off is the product I'm building right now.

321 Oak

A small studio, small on purpose

We build tools for daily life, from productivity to learning, with thoughtful design, honest interactions and the hundred small decisions that separate a working product from a good one. No ads, no dark patterns, and prices stated plainly.

We use AI openly in how we build. It speeds up the making, but the judgment, taste and final call stay human.

Checked Off

Public beta for Windows. Free, no account needed.

A personal productivity app for the rhythms of life, work and play. It is built around how one person actually plans a day, not how a team coordinates a project, with a bounded daily list, routines that keep going, and no guilt piling up when you miss a day.

321 Oak is also working on a free, open learning app for K-12, in early development.

Outside of work

Mostly outdoors.

I'm a boater, swimmer, kayaker, hiker and backpacker. I love the outdoors, I'm obsessed with plants, and I'm an avid gamer. I cook casually and garden, let's say, lackadaisically.

Oak-covered hills and a distant peak in the late afternoon light.
Reeds and a bare tree reflected in still water at dusk.