As CISO for Webroot, Gary Hayslip advises executive leadership on protecting critical information resources and oversees enterprise cyber-security strategy. His mission includes creating a “risk aware” culture that places a high value on securing and protecting customer information entrusted to Webroot. Hayslip’s career in the fields of enterprise information security and network security spans more than 20 years and includes multiple CIO, CISO, and deputy director of IT positions for the U.S. Navy, the Federal Government, and the City of San Diego.

In these positions, he was instrumental in architecting security programs from the ground up, auditing large, disparate networks and consolidated extensive legacy network infrastructures into converged virtualized datacenters. Hayslip recently co-authored the CISO Desk Reference Guide: A Practical Guide for CISOs – Volumes 1 & 2, which are considered among the leading books on enabling CISOs to expand their expertise and scope of business knowledge. He serves as an advisory member of the EvoNexus Selection Committee, where he reviews and mentors cybersecurity and Internet-of-Things startups.

He sits on the board of directors for both the Cyber Center of Excellence and the Infragard San Diego chapter. Hayslip is an active member of the professional organizations ISC2, ISSA, ISACA, OWASP, and Infragard. He currently holds several professional certifications, including CISSP, CISA, and CRISC. Hayslip has a BS in information systems management from UMUC and an MBA from San Diego State University.


Today We Talked About:

  • Origin Story
  • Balancing Usability and Security
  • Certifications for CISO’s
  • Risk Management
  • Cyber Security
  • SoftSkills
    • Patient
    • Tenacity
    • Time Management
    • Team Work
    • Dependability
    • Communication
    • Collaboration
    • Curiosity

Connect with Gary


Normally this is where I ask for a rating/review/subscribe, but instead, this month I’m asking that you make a donation for Breast Cancer Research in honor of Breast Cancer Awareness Month

October 29, 2018
Gary Hayslip

AGL 075: Gary Hayslip, CISO at Webroot

As CISO for Webroot, Gary Hayslip advises executive leadership on protecting critical information resources and oversees enterprise cyber-security strategy. His mission includes creating a “risk aware” culture that places a high value on securing and protecting customer information entrusted to Webroot. Hayslip’s career in the fields of enterprise information security and network security spans more than 20 years and includes multiple CIO, CISO, and deputy director of IT positions for the U.S. Navy, the Federal Government, and the City of San Diego. In these positions, he was instrumental in architecting security programs from the ground up, auditing large, disparate networks […]
October 25, 2018
martin wolfe

AGL 074: Martin Wolfe – Distinguished Engineer, CTO – IBM

Today on the show I have Marin Wolfe (Marty). Marty is a systems engineer, creator of new solutions and innovations, a leader and motivator of the best and brightest, and focused on delivering solutions to the most complex challenges and supporting key goals. Marty is an IBM Distinguished Engineer and CTO, a technical executive of which there are only 600 across IBM’s entire global enterprise. Marty’s combination of technical depth, business acumen and delivery expertise has resulted in over $500M in direct revenue helping to shape technical strategy and fixing the most challenging problems at all sizes of organizations and enterprises. […]
October 22, 2018
Heather Wilde

AGL 073: Heather Wilde is the CTO of ROCeteer

Today on the show we have Heather Wilde.  She was the eighth employee of Evernote, where she oversaw the company’s growth from thousands to 100 million customers. She’s published popular video games, trained Fortune 500 brands, advised hundreds of startups, and managed some major nonprofit programs. Now, as a fractional CTO through her own company ROCeteer, her award-winning work keeps the “Unicorn Whisperer” constantly traveling across the globe to find the next unicorn. About Heather Heather Wilde is a multiple award-winning, 6-time CTO, and 5x-certified Executive Coach. She is an Author, Speaker, Nonprofit Director, and Howard R. Hughes College of Engineering […]
October 19, 2018
Saying No

AGL 072: The Power of “Saying No”

I heard a story on the Accidental Creative Podcast once about pruning grapes in a vineyard.  Todd said that many times healthy vines that are bearing good fruit need to be pruned off.  The reason is that the vine cannot grow new, more productive branches until some of the other branches are pruned.  So cutting out good and fruit-bearing branches may be necessary in order for the vine to increase in capacity overall.  This holds with us at work and in life.  Sometimes we have to shutdown old dreams or projects, or stop doing old tasks that no longer provide […]
October 15, 2018
francesca-gino

AGL 071: Rebel Talent with Francesca Gino

Francesca Gino is an award-winning researcher and the Tandon Family Professor of Business Administration in the Negotiation, Organizations & Markets Unit at Harvard Business School. She is also affiliated with the Program on Negotiation at Harvard Law School, the Mind, Brain, Behavior Initiative at Harvard, and the Behavioral Insight Group at Harvard Kennedy School. Her consulting and speaking clients include Bacardi, Akamai, Disney, Goldman Sachs, Honeywell, Novartis, P&G, and the U.S. Air Force, Army, and Navy. She has been honored as one of the world’s Top 40 Business Professors under 40 by Poets & Quants and one of the world’s 50 most influential management thinkers by […]
October 8, 2018
Patricia Hatter

AGL 070: Patricia Hatter

About Patty Patty Hatter is a multiple award-winning technology, business and operations leader who drives digital transformation and growth for global companies. Patty currently advises early stage technology companies, focused on key technologies such as cybersecurity, cloud infrastructure, and blockchain-enabled enterprise applications. She also serves on the Board of Directors for Barrick Gold (NYSE:ABX). Prior to this, Patty was SVP of the McAfee Services organization, where she drove 50% growth. Previous to her role at McAfee Services, she served as general manager and CIO for Intel Security as well as CIO and SVP of Operations for McAfee. There she orchestrated […]