From Hacker to Cybersecurity CEO: Building Continuous Security Testing with Casey Cammilleri of Sprocket Security

We chat with Casey Cammilleri, CEO and founder of Sprocket Security, a Madison-based cybersecurity company that's revolutionizing how businesses approach penetration testing. Casey started as a solo penetration tester - essentially getting paid to legally hack into companies to find vulnerabilities - but realized he could help more organizations by building software to scale that expertise.What makes Sprocket Security different is their continuous approach. Instead of testing once a year like traditional security firms, they monitor organizations continuously, testing whenever there are changes or new threats emerge, so companies always know what their risks are.We explore Casey's journey from individual consultant to leading a team of cybersecurity experts, his approach to building company culture with both local and remote employees, and his thoughts on growing a tech business in Madison versus coastal markets. You'll also hear his practical advice for founders about when to focus on building versus pitching, and insights for anyone interested in getting started in cybersecurity.Segments00:00 - Intro01:32 - What Sprocket Security Does: Continuous Penetration Testing02:57 - Casey's Background as a Penetration Tester04:44 - Building Software to Scale Security Testing06:03 - Early Go-to-Market Strategy and Local Network07:14 - Early Challenges of Scaling from Solo to Team08:26 - Learning Leadership and Using Mentorship11:51 - Hiring Strategy: Local vs Remote Talent13:42 - Building Company Culture Across Distributed Teams15:04 - Sponsor Break (Headway)16:46 - How the Vision Has Evolved Over 8 Years20:04 - Running MadSec: Madison Security Community21:06 - Getting Started in Cybersecurity Career Path23:04 - Advice for Breaking Into Cybersecurity24:36 - Hardware Security vs Software Security Focus25:49 - What Casey Loves About Building in Madison26:53 - What Wisconsin's Tech Scene Needs More Of28:23 - Pitch Contests and Capital: Casey's Perspective32:43 - Build First, Then Sell: Casey's Bootstrap Philosophy34:57 - Balancing Innovation with Customer CommitmentsKey Topics Covered→ Building continuous penetration testing from the ground up→ Scaling expertise through software and automation→ Early challenges of hiring and building company culture→ Local vs. remote hiring strategies for specialized talent→ Growing a tech business in Madison's startup ecosystem→ When to bootstrap vs. seek investment funding→ Getting started in cybersecurity and penetration testingAbout Sprocket Security:Sprocket Security is an expert-driven offensive security platform that provides continuous penetration testing. Instead of testing just once a year, they monitor organizations continuously and test whenever there are changes that impact security or new threats emerge.Resources Mentioned:Sprocket Security:https://sprocketsecurity.comCasey Cammilleri on LinkedIn: https://www.linkedin.com/in/caseycammilleri/MadSec - Madison Information Security Grouphttps://www.meetup.com/madsec/TryHackMe - Cybersecurity challenges and traininghttps://tryhackme.com/ Podcast SponsorValency FundFlexible funding solutions designed for sustainable growth of Wisconsin companies.Learn more at https://www.valencyfund.com/🔻 Connect With Us 🔻Subscribe to the Startup Wisconsin Newsletterhttps://www.startupwi.org/Upcoming Tech and Startup Events in Wisconsin (400+ every year)https://www.startupwi.org/eventsFollow us on LinkedInhttps://www.linkedin.com/company/startup-wisconsin/Connect with Jacob Miller:https://www.linkedin.com/in/kineticbearInterested in being a guest? Reach [email protected] Wisconsin's mission is to connect, educate, inspire, and grow tech startup communities across the state, not just during events, but year-round. This podcast is part of that vision, creating deeper connections and sharing the knowledge that helps Wisconsin's startup ecosystem thrive.This podcast is made by your friends at Headway.https://www.headway.io