I Almost Left Cybersecurity | Rinki Sethi, CISO of Upwind, Founder of Lockstep

Rinki Sethi has spent nearly 25 years in cybersecurity, with stops at Walmart, eBay, Intuit, Palo Alto Networks, IBM, Rubrik, Twitter, Bill.com, and now Upwind. But one of the most important moments in that career came when she almost walked away from cybersecurity entirely.

In this episode of Random Access Memories, Rinki joins Jake Bernardes to talk about the mentor who changed the trajectory of her career, why the people around you can matter more than the logo on your résumé, and what great leadership actually looks like when the goal isn't just building better programs, but building better people.

They also dig into a question cybersecurity is going to have to answer sooner rather than later: What happens to the next generation of security leaders when AI automates the jobs where so many of today's CISOs learned the fundamentals?

From the rise of the “builder” CISO to technical fluency in an AI-first world, Rinki and Jake explore how the role is changing, and why knowing how to ask the right questions may matter just as much as knowing how to write the code.

Then, they look beyond the CISO seat. Rinki shares why she co-founded Lockstep, what she's learned from investing and working with founders, and why she believes security practitioners should sit at the center of the cybersecurity ecosystem instead of simply being sold to buy it.

Her biggest lesson after decades in the industry is also one of the simplest: Don't just chase the company. Chase the people.

Because the jobs change, the titles change, and the technology definitely changes but the relationships you build along the way can change everything.

In this episode The Walmart mentor who kept Rinki from leaving cybersecurity Why great careers aren't necessarily built by chasing prestigious company names What separates a true leader and mentor from someone who's simply managing people Why tomorrow's CISOs may need a builder mindset Whether AI actually makes everyone technical — or just makes it easier to build the wrong thing What happens when SOC, GRC, AppSec, and pentesting entry-level work gets automated How the CISO role is shifting from technical architect to business leader, communicator, and influencer Rinki's move from traditional enterprise security into hypergrowth security at Upwind Why she co-founded Lockstep and what investing taught her about the cybersecurity ecosystem Why practitioners should have a bigger stake in the value they help create The importance of understanding equity, cap tables, vesting, and startup economics Why networking and community aren't side quests — they're often where the next opportunity begins