INTRODUCTION
Meet Lenny Zeltser
From an early age, Lenny had security in mind. Building toy castles as a kid, he’d take extra precautions: planning ahead, adding reinforcements, and anticipating attacks so he could concoct the right solutions. It was an early start at building the mental models that would serve him in his security career.
That knack for protection – together with the drive to keep learning – helped Lenny quickly make his name in cybersecurity. Widely known and respected for his ability to reverse-engineer malware, Lenny has published books on the topic, regularly teaches classes, and has even been called the “Yoda of malware analysis.” But sometimes even Yoda can use some sage insight.
“Cybersecurity is an intersection of disciplines.”
CHALLENGE / WHY YASS
Searching for a sounding board – and more
Lenny first joined Axonius – an organization dedicated to understanding, monitoring, and securing some of the world’s most critical digital assets – as VP of Product. But in a matter of months, leadership saw his potential to lead security on a larger level, and he was invited to take on a new challenge as Axonius’ CISO.
Lenny had CISO’d in the past, but diving back into the role, he felt a little rusty. Soon enough, however, he was back in the groove. Then, a couple of years in, as the organization grew larger and more complex, he found that he needed an outside perspective. He craved a sounding board to help him clarify his mental models, smooth his path forward, and accelerate his success.
Both online and in person, Larry tried engaging with a variety of CISO communities. And his peers did offer guidance. But they had their own careers to manage, so the engagement only went so far. Lenny was looking for more – that same peer-to-peer connection but broader and deeper. Instead of a one-time conversation, he wanted an ongoing relationship that dug into details he couldn’t share without an NDA. He was hoping to build a shared understanding backed by the full context of the environment and players he was working with.
As soon as Lenny met Yael of Yass Partners (at a conference), he could tell she was a Yoda in her own right. Unlike other executive coaches, Yael had worked extensively and exclusively with CISOs – for years. Lenny also saw that she could quickly grasp the dynamics of a situation and provide an accurate read with insightful advice. “That’s someone I wanted in my corner,” he says.
THE YASS EXPERIENCE
Outside perspective on his innermost concerns
Two years into his role as CISO at Axonius, Lenny brought Yael on board. As the organization grew larger and more complex, it was becoming harder to build and maintain strong relationships, both with his reports and executive peers, and Lenny felt stretched thin. “Cybersecurity is really an intersection of disciplines,” Lenny has said. Building the right plan was important, but so was building the leadership and interpersonal skills to bring that plan to life.
“Itߴs a wonderful thing – to grow and be challenged and learn. But it’s even better with a friend by your side. An independent perspective who’s ultimately there to help you succeed.”
Lenny wanted someone to bounce ideas off of, talk things through with, and figure out where he really stood so he could stand firm. He was looking to blow off a little steam, sharing some of the concerns he was facing with someone who would encourage him and rally his efforts. At the same time, he wanted objective feedback, validation, and evaluation. How was he stacking up against other CISOs? What might he be missing?
Lenny engaged Yass Partners. Essentially, this meant chatting with Yael every two weeks for six months with clear goals in mind. Together, they created a visual framework outlining how to extend Lenny’s influence at the organization – making the mental models tangible with a clear blueprint for broadening support and bolstering relationships. Then, working against this roadmap, they checked back regularly to compare progress and notes, finding new and better paths forward.
“What are you working on? What challenges are you facing? Where could you benefit from a second opinion?”
Each time they met, Lenny could riff and reflect, putting his ideas into words. This wasn’t therapy, and it wasn’t just venting: Yael was there to provide informed opinions, straight answers, and prescriptive advice. “Yael would say, ‘Okay, you handled that this x way, and they reacted y way, which tells you z. So here’s what you should have said instead,’” Lenny explains. Yael translated his lived experience into objective standards he could steer by.
From managing teams to engaging with execs and preparing for board meetings, Lenny explored all the areas that had once made him uncertain. Yael initially provided outside support, but before long, she had gained insider perspective. As she began to understand the key players, their personalities, and their evolving relationships with Lenny, she could better tailor her advice: i.e., the right way to communicate with this colleague in this situation with that goal in mind.
POST-YASS / RESULTS
From one big change to another
As Lenny worked with Yael and Yass, he felt increasingly supported – and increasingly confident in his ability to deliver results. “It was nice just to be listened to,” he says. “Having someone pay attention to all the little ins and outs of my world and respond with full knowledge of the situation. It made me a better, more effective CISO, which doesn’t just help me. It ultimately adds value to the business at large.”
