EP4 - Caleb Sima: How to Hire and Retain a High-Performing Security Team — Lessons From Scaling at RobinHood

To build a high-performing security team, organizations must rethink how they approach recruiting, hiring, and retaining talent. The problem is, building a great team is incredibly challenging today. With an estimated 400,000 unfilled security jobs, security teams are understaffed, burnt out, and struggling to keep up with an ever-increasing number of cyberattacks each day.  Our guest today teaches us exactly what security leaders can do to overcome these challenges and build a high-performing security team. Caleb Sima is the Chief Security Officer at Robinhood. He’s spent more than 20 years in cyber security following the unconventional path of spending his early years as a founder before transitioning over to the operations side and leading security teams at organizations including Databricks, HP, and Capital One. This unique journey provides Caleb with a unique and interesting perspective that every security leader can learn from. 

Topics Discussed: 

• What incentivized Caleb to transition from a company founder to an operations leader — making the translation from an “arms dealer to a soldier on the battlefield”. 
• How Caleb's experience of building (and selling) his own startups shaped how he approaches being a CISO.
• Why security teams need to think about other internal departments as their customers.  
• How to know when it’s okay to let fires burn and how to communicate this decision with other leaders at your organization.
• Why outsourcing your number 1 priority of recruiting to someone else is a recipe for disaster.  
• Lessons learned from building the security team at Robinhood — bringing on 100+ new security people in less than a year. 
• How to instill a culture that believes hiring, talent, and people are important.
• Why security leaders need to focus on building a hiring pipeline.
• How take a data-driven approach to hiring and why time-to-hire is such an important metric to focus on.