Jessica Reid, founder of Simple Mondays, is among four Northern Ontario entrepreneurs — and one of three women — selected to pitch at Venture North Bay on November 5
A Gravenhurst entrepreneur is heading to North Bay this fall to pitch her bootstrapped tech company to investors. Jessica Reid, a former K-12 teacher and founder of Simple Mondays, an AI-powered planning platform for teachers, is one of four Northern Ontario founders selected for Venture North Bay Pitch on November 5, 2026 — and one of three women in this year’s lineup.
Reid’s idea for Simple Mondays started at her own kitchen table in June 2023, after a particularly difficult year of teaching and a bad case of burnout. Her own mental health was not good, and she felt she was missing some of the best years while her kids were young.
Looking for a better way, she discovered that AI could dramatically speed up her grading and planning. She spent the following summer teaching herself how to apply it to lesson planning and went back to school that September feeling, in her words, “clear, calm, and routine-driven, leaving by 3 p.m. to be home with her family. Over the next two years, without a technical co-founder, she refined the system. She taught it to fellow educators before turning it into Simple Mondays, a company now
used by teachers across Canada.
“I was an overwhelmed teacher, too,” said Jessica Reid, Founder and CEO of Simple Mondays. “Simple Mondays is the tool I wish I’d had — something built by a teacher, for teachers, that gives back the hours we lose to admin work so we can focus on the reason most of us got into this profession in the first place: our students.”
Simple Mondays combines AI-generated lesson plans, worksheets and resources, a customizable digital planner, and classroom management tools in one platform, and now also sells directly to schools through a school-wide licensing program, which the company is piloting for the 2026/27 school year.
Reid will share the Venture North Bay stage with fellow Northern Ontario founders Christine
Steger of MYXAR (Port Severn), Rachel Clark of SKADI Cyber Defence (Bracebridge), and
Aurelian Basa of Re-2Ox Technologies (North Bay), pitching for a $5,000 Judges’ Choice Award and a $3,000 People’s Choice Award, voted on by the audience. Hosted by Northern Ontario Angels (NOA) and Innovation Initiatives Ontario North (IION), the event runs from 6 to 9 p.m. at the Best Western North Bay Hotel & Conference Centre. It includes networking, appetizers, and a cash bar. Tickets are $30 and available on Eventbrite.
“Through our work at Northern Ontario Angels, we’ve seen how mentorship, investor
connections, and access to capital can make a meaningful difference for founders,” said Ian
Lane, Executive Director of Northern Ontario Angels. “We are excited to support these four
innovative companies as they take the stage and showcase the strength of entrepreneurship in Northern Ontario.”
Reid’s plans extend beyond Northern Ontario this fall. From October 25 to 31, 2026, she will travel to Paris and Versailles as part of the RFAQ (Réseau des femmes d’affaires du Québec) Trade Mission to France, attending its InvestHer Summit after PARO Centre for Women’s Enterprise, a mission partner, noticed her work on LinkedIn and invited her to take part. The trip will give Reid the chance to learn firsthand about the European school system and edtech policy landscape, alongside opportunities to network with industry leaders, education policymakers, and investors.
