The 16th CTO Colloquium: Confronting Quality Debt & The AI Security Gap
For modern engineering organizations, the "AI Revolution" isn't just about velocity — it's about the collapse of traditional oversight. As code generation approaches the infinite, we are witnessing the birth of a new, predatory risk: The Integrity Gap.
When AI-generated code enters your environment at scale, it doesn't just bring speed: it brings Quality Debt and Systemic Security Risks. We're building software faster than our teams can verify it — creating a "Boogeyman in the machine" that threatens the very foundation of product trust and long-term maintainability.
The 16th CTO Colloquium in Chicago is a working forum designed to shine a light on these invisible risks. We're moving beyond high-level AI hype to provide practical, tactical guidance for leaders navigating the precipice of high-velocity development.
The Core Themes
Three threads that will shape every conversation, talk, and forum session.
The Quality Debt Crisis
Identifying and addressing the invisible decay in AI-forward organizations before it becomes a structural liability.
The AI Security Surface
Investigating how rapid code generation opens new, subtle vulnerabilities that traditional security frameworks weren't built to catch.
The Verification Bottleneck
Strategies for maintaining "Founder-level" system knowledge and ownership in an era of automated output.
The Agenda
Day 1
Thursday, July 23
Optional Morning Meetup
For early arrivals — a casual 1-hour group activity (Lurie Garden & Millennium Park loop, or the McCormick Bridgehouse & Chicago River Museum).
Arrival & Security Sign-In
222 N LaSalle requires a front-desk security sign-in — please arrive by 2:30 so we can head up together.
Opening remarks & light refreshments
Ben Fellows · Founder, TinyIdeas
From Vibes to Verification: Fighting AI Quality Debt with Anchor Tags and Executable Dev Contracts
Ryan Vice · Cofounder & CEO, Vice Software
AI Engineering on Autopilot: Free Your Engineers for the Work That Compounds
Break
Tyler Ward · CEO, CSG-Cyber
AI Security Governance & Innovation At-Speed and Scale
Greg Svitak · VP of Engineering & Chief Software Architect, WorkWave
Project Alfred for QA: Spec-Driven Testing and the "Inception Mobbing" in the AI-SDLC
Debrief
Sponsored Happy Hour at Punchbowl Social
Drinks, food & games on us · 310 N Green St (West Loop) · ~10 min by CTA Green/Pink Line from Clark/Lake to Morgan
Day 2
Friday, July 24
Arrival, Check-In & Breakfast
Arrive by 8:00 to clear building security, grab our special coffee and breakfast treat, and settle in before sessions begin.
Keynote Session · Jay Aigner · CEO, JDAQA
QA is dead. What now? — A hands-on working session on rebuilding the validation layer for AI-accelerated engineering organizations.
Lunch at The Mart Food Hall
Inside the Merchandise Mart (222 W Merchandise Mart Plaza) — a 4-minute walk west across the Wells Street Bridge. Open seating with a variety of fast-casual options.
Sponsored Happy Hour · 7:00 PM
Punchbowl Social Chicago
Wind down Day 1 with drinks, shareable plates, and a little friendly competition (bowling, darts, arcade) on us. Open to all attendees.
Address: 310 N Green St, Chicago
Easiest commute: Walk 5 min from 222 N LaSalle to the Clark/Lake CTA station, take the Green or Pink Line one stop west to Morgan, then walk 3 min south. Door-to-door in ~10–12 min.
The Lineup
Operators sharing hard-won lessons on AI-assisted development, security, and engineering throughput.
Previous Colloquiums
A glimpse of the conversations, candor, and connection that define the CTO Colloquium experience.
Chicago · Venue & Stay
Hotel Recommendations
Three vetted options near 222 N LaSalle
All three are a short walk to the venue and within the same mid-tier budget. Click any card to flip it and see the map.
Who This Is For
This colloquium is best suited for CTOs, VPs of Engineering, and senior technical leaders who value deep conversation, trusted peers, and practical leadership growth over surface-level content.
Presented by
CTOs face daily high-stakes hurdles. 7CTOs is an exclusive tech leader membership providing expert support, coaching and community to help CTOs lead, grow, and thrive.
Proudly sponsored by
JDAQA solves the QA problem for growing software teams. Headquartered in Philadelphia, PA, we combine AI-enabled test automation with decades of complex real-world software quality assurance experience. JDAQA helps deliver robust, reliable software that ships with confidence.