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Windy City EdTech · Aug 11, 2026

Rethinking the gradebook + Launching our Future of Learning Meetup 🚀

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Margot Toppen · Windy City EdTech

Monthly notes from The EdTech Institute of Chicago

Welcome to the EdTech Institute of Chicago’s August newsletter! EIC is a volunteer-led organization with a mission of elevating Chicago and the Midwest as a world-class hub for edtech innovation.


What’s included:

The energy was high and conversations were flowing at the EIC Techwalk this past weekend. Thanks to all who came out and to Chrystal Price, Shara Deepankar and Caroline Gomes from TechWalk Chicago for partnering with EIC on this fun networking event.

EIC member Isabel Hutchison is taking the lead on planning a new networking opportunity for our community, with a goal of cultivating conversation between researchers and edtech leaders.

The first EIC Future of Learning meetup will take place September 15 at Pilot Project Chicago and all are invited to attend!

> Grab your spot here!

David Wartowski has a complicated relationship with the gradebook. Two decades into a teaching career, most recently as K-8 district-level math director, he’s watched the tool meant to capture learning end up measuring compliance instead.

Learning Portrait is his answer: a reimagined gradebook “designed from the ground up to actually think the way innovative teachers think about grading.” As he puts it, “Teachers who grade for learning have long been forced to translate students’ learning into a soulless compliance tool... that runs counter to the way they think about teaching and learning.”

Learning Portrait runs on what David calls logic-based grading: a school describes how it defines mastery in its own words, and the platform applies that logic for every student. No points, just words. What a family opens is not a running average. It is a portrait of what a student was asked to learn, where they are, and what to do next. Students rate their own proficiency against clear standards and back it up with authentic work, building a record that reflects what they can actually do, and how they’ve grown.

Impact Over Features

As Learning Portrait has grown from pilot classrooms into paid district partnerships, what’s stuck with David isn’t the product roadmap. It’s the people. “Making a difference isn’t about features, it’s about the story and real human connections,” he says. Where he used to lead with a list of what the platform does, he now leads with what it makes possible, sharing “stories from real classrooms and in teachers’ and students’ own words.”

That same instinct shows up in how he handles rough patches. “People would rather have a tool that is still growing and backed by a team that listens and responds than to have a polished tool with no one behind it,” David says. “We listen intently for what our partners really need, which is usually deeper than what they first say, and the gold is in solving that. Deep listening is where the joy and the impact live.” For David, growth is not about angling toward an acquisition. It’s about shifting how schools think about learning and assessment altogether.

Advice Rooted in Values

Asked what he’d tell other edtech founders, David didn’t talk about fundraising or growth hacks. “Avoid venture capital if you can,” he says. “Stay rooted in your values in every action. Build a team that makes you better, and empower them. Stay passionate. Dream big. Watch every dollar. And where you are scared, get curious, because that fear is very likely pointing at exactly where you need to focus.”

Community, Not Competition

David has taught in the Chicago area for over twenty years, and he’s found a kindred community in EdTech here, too. “This is like the Silicon Valley of EdTech! It’s awesome,” he says. “A genuine space where people want to support each other and get meaningful work done. That’s a great feeling.” It’s a fitting note for a founder whose whole approach is less about beating the competition and more about building something worth showing up for.

Why It Matters

Every school that moves toward standards-based grading hits the same wall: the gradebook can only count. Learning Portrait’s bet is that you cannot ask teachers to grade for learning inside a tool built to measure compliance. Fix the tool, and the practice finally has somewhere to live.

See how logic-based grading works at learningportrait.com

  • Career Week | August 17-21
    Archer Career is offering a full week of hands on, expert guidance and AI support work on credentials that drive job searches forward.

  • It’s Your Call: Making a Positive Impact in Virtual Interviews | August 28
    Code Social is sponsoring an opportunity to join Jennifer Wonderly, Program and Coaching Director at the Career Transitions Center (CTC), for a practical session on feeling more prepared and confident in virtual interviews.

  • NEW! Future of Learning Meetup | September 15
    ​This series is for edtech builders, educators, researchers, and anyone curious about where technology and learning are headed. Whether you’re designing learning products, teaching in a classroom, or just interested in this space, this event is designed to help you in your work and in your thinking.

  • VOTE NOW - SXSW SESSION PROPOSAL: EIC community member and former steering committee leader Monica Para has a SWXSW session proposal that needs your support! Take a minute to vote for her session on achieving your goal in 90 days with the proper structure, no excuses.

  • Overture is hiring teachers! If you know anyone who appreciates a paper and pencil approach to teaching AI or would like to try your hand at it, you can apply to join the Overture team at www.overtureai.org/careers

  • Education Walkthrough is hiring a customer success manager. Chicago is the preferred location for this opportunity to be part of EW’s next stage of growth. Apply here.

🗓️ SUBMIT events & announcements for our next newsletter!

  • Know someone who would be interested in our community? Those interested in joining may apply here

  • Once members are approved, they will be invited to join our What’s App chat group, where members can interact freely any time!

Got something the community should know? Share a win, an event or an opportunity — we’ll amplify it next month.

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