Matt Nupen
Product Management · Accessibility & EdTech · AI for Learning
I’m a product manager building products that make the world more inclusive — in edtech and beyond. I do my best work on small teams: early-stage startups and scrappy teams inside larger organizations.
Currently looking for: Head of Product, Director of Product, or Senior PM at a mission-driven edtech, accessibility, or AI-for-learning company. Remote (based in Duluth, MN) or Minnesota hybrid.
1M+
Users served
15 yrs
In classrooms
10 yrs
Building product
~$100K
Bootstrapped ARR
About
I’ve spent ten years building products: co-founding InsertLearning and scaling it from zero to a million users and acquisition, leading accessibility products as Senior PM at Benetech, and now shipping AI-powered learning tools like LetsChat, VisSched, and My Classroom Assistant.
What sets my product work apart is fifteen years in classrooms teaching chemistry, computer science, and business. Teaching is daily user research — I don’t have to guess what users need, because I’ve spent my career watching real people hit real problems and building for them. It’s why talking to 300+ teachers came naturally when growing InsertLearning, and why my recent launches all started as problems I saw students hit in my own classroom.
Inclusion drives my work. It comes from years working with at-risk teens, a belief that equity belongs in products from day one, and my teenage daughter — who uses a wheelchair, communicates non-verbally, and co-developed LetsChat with me.
Featured work
Zero to 1M users
InsertLearning
Co-founder & CEO, 2014–2020 · Acquired
Co-founded a Chrome extension that turned any webpage into an interactive lesson. Talking to 300+ teachers got it from zero to 1M users, growing through grassroots teacher-to-teacher adoption.
Result: 1M+ users worldwide, bootstrapped to ~$100K ARR profitability, Google Top Chrome Extension of 2019, acquired in 2020.
Accessibility
Benetech: Mathshare + Imageshare
Senior Product Manager, 2019–2020
Led product on two accessibility tools serving students with disabilities at a Palo Alto nonprofit. Applied WCAG throughout, ran efficacy studies with real students, and shipped features informed by field testing in classrooms.
AI for learning · Now
LetsChat AAC
Founder, 2024–present
An AI chat app built for teens with disabilities. This iOS app is a fun, judgment-free place to practice communicating with AI characters. Four accessible input modes, TTS with karaoke-style highlighting, and a variety of other inclusive features built for and WITH young adults with disabilities. Launching in the App Store.
AI for learning · Now
VisSched
Solo build, 2026
Free, account-free visual schedule and class timer for K-12 classrooms. Built from a problem I watched repeatedly in my own classroom. Evidence-backed and aligned with UDL and CASEL frameworks.
What I’m looking for
- Role: Head of Product, Director of Product, Principal or Senior PM
- Stage: Seed to Series B preferred; established companies welcome
- Mission: Edtech, accessibility, AI for learning, social good, public sector
- Location: Remote (based in Duluth, MN) or Minnesota hybrid
Beyond work
Writing: I write about product, education, and accessibility on my blog.
Jackpine Print: A father-son shop in Duluth making one-of-one cut-vinyl designs sketched from customers’ adventures — each design serialed, cut once, and retired forever. jackpineprint.com
Making: Building a sauna, wheelchair costumes, duct-tape truck art, and 3D designs on Thingiverse.
Connect
Email: matt.nupen@gmail.com
LinkedIn: linkedin.com/in/matt-nupen/
Twitter: @mattnupen
Thingiverse: Thingiverse.com/Whampus