What Makes a Great CISO? A Playbook from Gary Hayslip

What Makes a Great CISO? A Playbook from Gary Hayslip

What separates a great CISO from a great one? In this powerhouse conversation, Ron invites friend and cybersecurity leader Gary Hayslip, CISO at SoftBank Investment Advisers, back on the mic to discuss what it takes to lead in today’s high-stakes digital world. Gary shares battle-tested insights on accountability, the evolving expectations of the CISO role, and how AI is reshaping leadership without replacing it.

Gary shares stories ranging from military mishaps to enterprise-scale transformation, and makes the case for visibility, trust, and embracing change. His perspective brings clarity to the fundamental responsibilities of a CISO and the mindset required to lead with impact.

Impactful Moments

00:00 – Introduction

02:00 – Defining the modern CISO as a business leader

05:45 – Why CISOs should never delegate accountability

07:30 – The danger of staying invisible

10:45 – The $40K UPS explosion mistake

15:00 – How leaders build trust in new teams

19:10 – Visibility is not micromanagement

24:30 – Staying humble while leading big

30:00 – Building “Rocky the Raccoon” internal GPT

34:30 – Hiring for AI fluency in security teams

Links:

Connect with our guest, Gary Hayslip: https://www.linkedin.com/in/ghayslip/

Check out our upcoming events: https://www.hackervalley.com/livestreams

Join our creative mastermind and stand out as a cybersecurity professional:

https://www.patreon.com/hackervalleystudio

Love Hacker Valley Studio? Pick up some swag: https://store.hackervalley.com

Continue the conversation by joining our Discord: https://hackervalley.com/discord

Become a sponsor of the show to amplify your brand: https://hackervalley.com/work-with-us/

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Episode 54 - Hiring Leaders and Finding Talent with Alex Maestretti

Episode 54 - Hiring Leaders and Finding Talent with Alex Maestretti

In this episode we sit down to chat with Alex Maestretti, CISO of Remitly. In this conversation, we explore finding talent and the unique challenge of hiring managers. Chris also shares his unique relationship to Alex. Alex's LinkedIn: linkedin.com/in/maestretti Alex's Twitter Handle: @maestretti Remitly's Website: https://www.remitly.com/us/en

9 Huhti 202016min

Episode 53 - In the Depths of Deception with Jenny Radcliffe

Episode 53 - In the Depths of Deception with Jenny Radcliffe

Psychology is a major pillar of Social Engineering 🧠. In this episode, we brought in a true expert, Jenny Radcliffe - A burgular for hire, a professional con-artist, and an expert in Non-verbal communications. This episode had Chris and Ron on the edge of their seats. To learn more about Jenny Radcliffe: @Jenny_Radcliffe https://humanfactorsecurity.co.uk/

6 Huhti 202039min

Episode 52 - From Librarian to OSINT with Tracy Maleeff

Episode 52 - From Librarian to OSINT with Tracy Maleeff

Open Source Intelligence (OSINT) is "data collected from publicly available sources to be used in an intelligence context". Performing OSINT is a critical aspect in triaging cybersecurity related events. In this exciting episode, Ron and Chris bring in an OSINT expert with the ultimate background for finding open source data. Tracy Maleeff aka InfoSecSherpa, is a seasoned expert in library science and security analysis. Be sure to listen in on this episode and gain insight for how library science applies to all aspects of life.

1 Huhti 202040min

Episode 51 - A Threat Intelligence Journey with Doug Helton

Episode 51 - A Threat Intelligence Journey with Doug Helton

Can Threat Intelligence Analysts do the same in the professional space as the Threat Intel Analysts depicted in movies? Yes, as long as you have the same level of skills and tools as the characters in the movie. Doug Helton joins this episode to share his experience in Cyber Threat Intelligence and acquiring skills required to be highly effective.

30 Maalis 202023min

Episode 50 - 50th Episode and Beyond with Ron and Chris

Episode 50 - 50th Episode and Beyond with Ron and Chris

🎊Happy 50th Episode! This episode couldn't have been possible without our amazing guests and listeners! Looking into the future, we are excited to share new content and resources that we've been working on. HackerValley.Studio Website Hacker Valley Studio Patreon

25 Maalis 202028min

Episode 49 - What is Your Superpower with Yael Nagler

Episode 49 - What is Your Superpower with Yael Nagler

Everyone has a superpower and it's not uncommon to have more than one. In this episode, Chris and Ron discover and share what their super powers are with Yael Nagler. Yael is a security tinkerer and has an amazing ability of bringing together people in technology.

23 Maalis 202028min

Underrepresented Episode 2

Underrepresented Episode 2

This is the second episode of the Hacker Valley Studio and ITSP Magazine co-production focused on underrepresented populations in technology.In this episode we highlight Nelson Abbott from NPower and Charles Nwatu from /Dev/Color.So many powerful statements in this one about organizations fighting for representation and awesome thoughts on being a role model

19 Maalis 202045min

Episode 47 - The Role of a CISO with Lenny Zeltser

Episode 47 - The Role of a CISO with Lenny Zeltser

In this exciting episode, Lenny Zeltser - CISO @ Axonius joins the podcast. Lenny is someone we really enjoy speaking to and is an all around expert in malware, technical writing, and managing teams to success.

18 Maalis 202021min

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