AI Native Roadtrip - Chicago
The AI Native Dev Community is going on a roadtrip!
AI is transforming software development and we’re excited (and curious!) about what comes next.
Are you building software with AI, perhaps using agentic workflows?
Or building tools that build software with AI?
To start answering these questions, we’re hitting the road this fall to connect with builders, founders, and developers shaping the future of AI-native development.
Each stop is an evening of lightning talks, real-world demos, and candid conversations about what it really takes to build with AI today.
🙌 Big thanks to Microsoft for hosting, and shout-out to our amazing partners AI Collective and Tessl for helping make the magic happen!
Program
6:00pm – Doors open
6:30pm - Kick off and message from our partners
6:45pm – Talks (~3 × 20 min)
Spec Driven Development: Why your prompt chaos won’t scale - Macey Baker
AI: Your New Pair Programmer - David Giard
Rethinking Software: The AI Native, Event-Driven, Multi-Agent Paradigm - Mary Grygleski
8pm – Networking
9pm – Wrap-up
This session introduces Spec Driven Development (SDD) for AI coding, replacing ad-hoc prompts with human-readable specifications to improve code reliability, collaboration, and adaptability. Real-world examples show how SDD enables scalable, testable AI development, addresses challenges like spec drift, and supports smoother iteration and teamwork beyond freestyle prompting.
Macey Baker - Community Engineer at Tessl
As Tessl's Founding Community Engineer, Macey Baker is busy helping to build the future of AI-native development (and helping you build it too). Now an AI code generation obsessive, she got her start as an early employee at tech unicorn Intercom in San Francisco, before jumping the pond and roaming the London startup scene, working primarily in big data / ML houses. Some of her best friends are LLMs.
AI is now your virtual Pair Programming assistant - providing you with boilerplate code, write tests, document code, and increase developer productivity. Developers can take advantage of Large Language Models interacting with natural language. In this session, you will learn how to be a more productive developer, increasing the velocity of your software development, using GitHub Copilot.
David Giard - Partner Solution Architect at Microsoft
David Giard is a former accountant and a former biochemist, who has been developing solutions using Microsoft technologies for over three decades. Currently, David helps people design and build solutions in his role as a Partner Solution Architect at Microsoft. David has been very active in the developer community, speaking at numerous major conferences, code camps, and user groups around the world; helping to lead user groups; and helping to organize conferences and other geek events. He is the host and producer of the mildly popular online TV shows Technology and Friends and GCast. He is the co-author of the Wrox book Real World .NET, C#, and Silverlight. You can read his latest thoughts at DavidGiard.com. His hobbies include video, photography, sports, and embarrassing his sons.
This talk explores how adopting AI Native Development transforms both team culture and system design—from deterministic programming to orchestrating adaptive agent collectives, from static pipelines to fluid, event-driven networks. By making AI the foundation, and not an afterthought, organizations can create applications that continuously learn, reason, and evolve on their own terms—delivering on the true promise of intelligent software in a multi-agent world.
Mary Grygleski - Regional Director (East) at The AI Collective
Mary is a Technical Advocate, Java Champion, and the Regional Director - NA East at the AI Collective, a non-profit, grassroots community and think tank in the AI space. She started her career as a software engineer, and eventually discovered her deep passion in the advocacy space. She's an active tech community builder, and currently the President of the Chicago Java Users Group as well as an Organizer of The AI Collective Chicago Chapter.
This event is brought to you as part of the AI Native Dev Community. Consider subscribing to the Mailing List, Podcast, and join our Discord Community
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