The upshot of (un)continuous compliance
Featuring
Todd Dekkinga
Todd Dekkinga, CISO and COO of Cyber Way USA, joins Scrut's CEO Aayush Ghosh Choudhury to talk security, startups, and what “continuous compliance” really means. With 25+ years of experience and stories from advising Zoom, Box, and beyond, Todd shares sharp, candid advice you won’t find in your average audit checklist.


The upshot of (un)continuous compliance
The upshot of (un)continuous compliance
Todd Dekkinga, CISO and COO of Cyber Way USA, joins Scrut's CEO Aayush Ghosh Choudhury to talk security, startups, and what “continuous compliance” really means. With 25+ years of experience and stories from advising Zoom, Box, and beyond, Todd shares sharp, candid advice you won’t find in your average audit checklist.


Description
In this episode, we explore Todd’s unorthodox path to compliance, GRC, and risk management – a testament to the diverse paths that can lead to a career in risk management.
He highlights the pivotal moments that shaped his expertise, including the dot-com crash of 2001 and his work in highly controlled environments like biotech.
Todd discusses the common mistakes startups make during the SOC 2 compliance process and offers practical advice on maintaining compliance post-certification.
He also elaborates on the role of automation in GRC, particularly in optimizing compliance efforts for companies of different sizes.
Todd’s insights will provide valuable perspectives on navigating the complexities of compliance and risk management. Tune in to uncover the true upshot of continuous and non-continuous compliance!
Highlights from the episode
- Navigating compliance in startups vs. large companies
- The role of automation in GRC
- Practical tips for continuous compliance
"One common mistake among startups is neglecting to maintain compliance post-certification. Many overlook the continuous monitoring required, leading to frantic efforts to catch up during surveillance audits."
About the Risk Grustlers Podcast
Risk Grustlers is a podcast for people working in security, risk, and governance who want sharper conversations than the usual industry soundbites. Each episode features CISOs, security leaders, and risk practitioners sharing how they think through the real operational challenges behind cybersecurity, compliance, AI governance, and enterprise risk.
Hosted by Aayush Ghosh Choudhury (CEO and Co-founder of Scrut Automation) and Nicholas Muy (CISO at Scrut Automation), this podcast series focuses on practical lessons, hard-earned perspectives, and the nuance that comes only from years spent in the security and compliance space.


























