CISO Confidential Podcast: How a CISO Turned a Misstep into a Playbook for Cyber Resilience

From vendor strategy to board communication, Anand Singh, a former CISO at UnitedHealth, offers practical insights for CISOs on navigating complexity at enterprise scale.

In this episode of CISO Confidential, SAFE’s CEO Saket Modi sits down with Anand Singh, former Chief Information Security Officer at UnitedHealth Group’s Optum Insight healthcare technology and data unit, to uncover what it truly takes to lead security in one of the world’s largest and most complex organizations. 

Anand opens up about the emotional weight of missteps, how a $10 million security investment went sideways, and what he’s done since to drive smarter, risk-driven decisions.

The big learning: “We should have taken a more risk-driven mindset to the technology selection process…meaning we are looking at the kinds of things that would impact the organization” as opposed to only following a rules-based approach.

Anand’s career spans both large enterprises and high-growth startups. He brings deep expertise in building risk-driven security programs, aligning cybersecurity with business goals, and fostering innovation through secure technology adoption. 

Prior to his current role at Symmetry Systems, he held senior leadership roles at organizations including Alkami Technology and Target, where he oversaw large-scale security initiatives and complex technology deployments.

Key Takeaways from the Podcast

>>Reframe setbacks as strategy—Anand shares how a major rollout failure reshaped his cybersecurity approach.

>>Risk-first thinking beats checkbox compliance—build security programs on risk exposure not just audits.

>>Stay close to the practitioners —engage those deploying tools daily, not just those signing vendor contracts.

>>When briefing the board or the CEO, remember they are less interested in the technology than “how is my business being driven by the actions that the CISO is taking?”

Fast-Forward to Best Insights

00:00 – Welcome & Intro to Anand

00:34 – The Reality of a CISO’s Day

01:31 – A $10M Cybersecurity Investment That Missed the Mark

03:24 – Lessons Learned & What Should’ve Been Done

05:00 – From Tech-Speak to Board-level Storytelling that Resonates

06:47 – Reflections–learning from Cross-Industry Leaders at the FAIR Conference

08:48 – Final Thoughts

Watch this episode of CISO Confidential with Saket Modi and Anand Singh – and learn from more CISOs in the podcast series.