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Chicago’s dynamic edtech community recently gathered for the inaugural Chicago Edtech Extravaganza—an event designed to unite educators, technologists, and startup enthusiasts committed to transforming the landscape of education. This summit fostered an environment of creativity, collaboration, and forward-thinking, reinforcing Chicago’s emergence as a leading hub for edtech innovation.
A major highlight of the day was the 2025 Midwest All-Edtech Awards, presented by Startup Grind. Among the winners recognized for their contributions to education technology were:
- Archer Career – Pam Schilling, MBA, DBA
- ASL Aspire – Ayesha Kazi
- BāKIT Box – Shelley Gupta
- Headrush Learning Inc. – Mike Hourahine & Shane Krukowski
- REACH Pathways – Brooke McKean & Jeffery Beckham Jr
- Screencastify – Vishal Shah
These outstanding organizations are making a significant impact in the edtech space, each bringing innovative solutions to enhance education and learning.
Fireside Chat with Vishal
The event featured an inspiring fireside chat with Vishal, who shared his entrepreneurial journey with Rajiv Nathan.
Vishal reflected on the early challenges of building his first company from the conference room of his former employer’s office, highlighting the resilience and determination that fueled his entrepreneurial journey.
Starting with Kaplan as a key client, shifting gears toward sales-driven strategies, and eventually closing a $50 million deal without outside investmen- —his story was both compelling and inspiring. Now, as the leader steering Screencastify’s continued expansion, he emphasized the importance of community-driven innovation in the edtech space.
Midwest All-Edtech Award Winners Showcase
Following the fireside chat, the event transitioned into an interactive segment where the five Midwest All-Edtech Award winners took the stage. Each founder delivered their pitches, detailing their company’s vision, impact, and future goals. What set this showcase apart was the community feedback and resource-sharing session that followed, allowing for meaningful engagement, idea exchange, and potential collaborations among attendees.
The Future of Edtech in Chicago
The first Chicago Edtech Extravaganza proved to be more than just a networking event—it was a catalyst for innovation. With a room full of founders, investors, and educators committed to improving education through technology, the event set the stage for future breakthroughs in the field.
As Chicago continues to establish itself as an edtech powerhouse, events like these ensure that the right minds are connecting, collaborating, and pushing the industry forward.
