From CISO to Field CISO: Trust, Burnout & the Cost of the Role | Tim Chase, Field CISO, Orca

What happens after you finally get the CISO job you've spent your career working toward, and realize you want something different?
Tim Chase made the move from operational CISO to Field CISO because he loved something specific about the job: talking to other security leaders, understanding their problems, sharing what he'd learned, and helping them find better answers.
But becoming a Field CISO introduced a different kind of pressure.
In this episode of RAM, Tim joins Jake Bernardes to talk about what the role actually looks like when you strip away the conference stages and LinkedIn posts: defending whether you're still a "real" CISO, pushing back when companies treat Field CISOs like salespeople with impressive Rolodexes, and trying to remain credible when your paycheck ultimately comes from a vendor.
They also get into the part of the job that's harder to see: the cost to your family.
It's a theme that came up with last week's guest, Avani Desai, too. Avani talked about one year when her career meant she saw her infant son only 50 days. For Tim, it's the conferences that overlap with the first week of school, the travel squeezed between kids' sports and date nights, and the guilt of knowing that being present somewhere often means being absent somewhere else.
Different careers. Same uncomfortable question: How much of your life are you willing to give your job?
Tim is a father of four with a working spouse. Being useful in the field means customers, conferences and teams constantly compete for his time. But every yes somewhere is a no somewhere else.
Sometimes that means squeezing family life between trips. Sometimes it means sitting at a hockey game feeling guilty because his wife is home putting four kids to bed. And every year, Black Hat somehow lands during his children's first week of school.
For Tim, being a great Field CISO isn't about being everywhere. It's about knowing where you're actually valuable, and having the discipline to say no everywhere else.
This is a conversation about trust, credibility, career identity, burnout, family, and why sometimes the best thing a Field CISO can tell a customer is: Don't buy our product.
In this episode
Why Tim left an operational CISO role after spending years getting there
Whether becoming a Field CISO is a progression, a lateral move—or a step backward
Why some security leaders don't consider Field CISOs "real" CISOs
Whether Tim would ever return to an operational CISO seat
The misconception that Field CISOs are salespeople with CISO networks
Why lived experience gives a Field CISO credibility with customers
Why solving the customer's problem has to matter more than selling your product
Times Tim has told prospects that his own company wasn't the right solution
Why trust matters more than the product pitch
The travel and visibility expectations that come with being a Field CISO
Balancing conferences and customer commitments with four kids and a working spouse
Why Tim refuses to become a "road warrior"
The guilt that can come with being present professionally and absent personally
Why saying no is part of staying effective
What burnout looks like in a Field CISO role versus an operational security role