​*All existing community members will be approved. Non-community members must be nominated here. Nominations will be reviewed by the community.

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​Join the Chicago Ventures CTO Community for our 2026 Summit!

​Who's attending?

​A curated group of CTOs and most senior engineering leaders at early to growth-stage, venture backed tech startups.

​This event is invitation-only, but you can nominate a guest here. Space is limited.

​What to expect?

​5 hours of peer-led content and real discussions on practical decisions CTOs are faced with today. Plenty of time for networking and collaborating.

​What's expected of me?

​Given the group size and format, all attendees are expected to be active participants. This means contributing to group conversations and volunteering to lead or present.

​The entire event is off-the-record.

​Who are the hosts?

​Chicago Ventures, in partnership with Steve Gall (M1 CTO), Eric Lunt (serial CTO and startup advisor), and Dom Scandinaro (Cameo CTO).

​Agenda

​12:00pm - 1:00pm

​Lunch, Introductions and A Look Into the Future

​Come prepared to share 1 thing you need help with and 1 thing you'd like to discuss. We'll also spend time reviewing the 2026 predictions many of you shared in Q1. (Who has bets on the price of BTC in June? The temperature in Chicago?) Prizes for the top respondents!

​1:00pm - 2:30pm

​Breakouts

​We'll divide into groups or stay together to do deep dives into topics you want to discuss. Approx 3x30 min conversations. Topics may include (we will decide ahead of time what will be covered!):

• ​Agent orchestration

• ​Security planning around AI adoption

• ​AI coding workflows and impact on product mgmt

• ​In-person community and workspaces

• ​Hiring and developing juniors.

• ​CTOs role in the board room.

• ​How do you agree upon and document/enforce coding standards in world of agents?

• ​Corporate Agentic Harness/Control Planes

• ​Packaging and Pricing for AI products

• ​Forward Deploy Engineer vs Self Service experiences with AI

• ​Interviewing/Roll expectations with AI first engineers

• ​Enabling an effective "out of the box" AI tool setup for engineers and non-engineers alike

• ​Striking the right balance between encouraging individual AI trailblazers and central definition of AI use cases

• ​Should non-engineers have a path to initiating real code changes using AI tools? Where should engineers be in that loop?

• ​AI-first software engineering best practices and optimizations

• ​Enterprise AI governance

• ​New sdlc models for AI

• ​New team ratios and structure with AI

• ​Validation loops for fully autonomous coding agents.

• ​Anyone doing anything cool with AI + their CS solution

• ​Marketing in the world of AI?

• ​Are folks still finding SEO useful or should it be AEO lead

​2:45pm - 3:30pm

​Show and Tell

​Time for you to take the stage. Attendees will sign up for 5-10 minute presentations on whatever you'd like - personal or professional (can anyone top last year's "AI vs. Squirrels"?).

​Confirmed speakers include:

• ​Steve Gall (M1): Agent Orchestration

• ​Eric Lunt (Serial CTO): Creative ideas for home automation with Home Assistant

• ​Dom Scandinaro (Cameo): Cameo’s agentic strategy/deployment

​3:45pm - 4:15pm

​Demo with Straiker.ai

​4:15pm - 5:30pm

​Reception

​Light appetizers and drinks.

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​SUPPORTERS

​Thanks to our Venue Sponsor: Attain

​Thanks to our Reception Sponsor: Straiker