Scaling With Confidence: Operational Risks Early-Traction Founders Often Miss
CSE Learning Series Session #6
Founders Only | Virtual | Cameras On
Operational reality arrives often before founders are prepared for it.
⇨ A customer asks about security practices.
⇨ A contractor relationship becomes complicated.
⇨ A founder disagreement turns into a business problem.
⇨ Sensitive data ends up somewhere it shouldn't.
⇨ A contract creates obligations no one fully understood.
The challenge isn't that founders don't care about risk.
It's that most founders don't know which risks actually matter at their stage—and which ones can safely wait.
Join Chicago Startup Events and Brian Cavanaugh, Founder & Managing Partner of Finsure, for a practical discussion focused on the operational risks that begin appearing as startups move from early building into real customers, real partnerships, and real growth.
This session is designed for founders who are asking:
• Are we exposed already?
• What can realistically break at our current stage?
• What mistakes are founders like us making?
• What operational risks matter now versus later?
• What should we address before we waste time or money?
This is not an insurance sales presentation.
It's a founder-focused session on operational readiness, preventative thinking, and practical risk management for companies navigating early traction and growth.
What We'll Cover
• The founder assumptions that create unnecessary risk
• Common operational, cyber, hiring, and contractual blind spots
• What operationally mature startups do earlier
• Practical ways to reduce exposure before problems occur
• Where insurance fits within broader operational readiness
Who Should Attend
• Bootstrapped, pre-seed, and seed-stage founders
• SaaS, AI, fintech, healthtech, marketplace, and technology startups
• Founders with customers, pilots, users, contractors, or partnerships
• Teams preparing for growth and operational scale
What You'll Walk Away With
• A clearer understanding of your current operational exposure
• Awareness of the most common startup risk blind spots
• Practical actions you can implement immediately
• Better judgment around what matters now versus later
Format
✔ 60 minutes
✔ Founder-only discussion
✔ Practical framework and examples
✔ Live Q&A
✔ Cameras on — highly interactive session
Speaker
Brian Cavanaugh
Founder & Managing Partner, Finsure
Brian Cavanaugh is the founding principal of Finsure, an international insurance brokerage based in Chicago. Prior to founding Finsure, Brian spent six years as a partner with WTW, advising venture capital firms, asset managers, broker-dealers, investment banks, hedge funds, and technology companies on risk management and insurance strategy. Previously, he served as Vice President of Private Equity Insurance Placement at Aon in New York and began his career underwriting management liability risks for financial services firms at CNA.
Hosted by Krystal Rogers, Founder, Chicago Startup Events
Operate in Sequence. Build Evidence Before Scale.