In the bustling arena of cybersecurity, innovation is the key, and Zach Wasserman, CTO of Fleet, is a name synonymous with cutting-edge solutions. As a California native who now resides in the scenic landscapes of British Columbia, Zach has been a driving force behind Fleet's mission to empower businesses with state-of-the-art cybersecurity measures. In our exclusive interview, we dive deep into the journey of a tech-savvy lone wolf transforming into a hands-on leader. From his early days as a consultant to helming a team representing at least eight countries, Zach's story is one of growth, adaptation, and passion. His company's unique open-core model, offering premium enterprise-licensed features with an open-source approach, stands as a testament to the innovation he fosters. But who is the man behind the machine? Zach opens up about his personal life, his love for risk management, and his dedication to long-term goals. Join us as we explore the world of Fleet, a modern cybersecurity enterprise, and the visionary leading it.

Zach Wasserman: From California's Sunshine to British Columbia's Tech Bloom - A Candid Chat with Fleet's CTO

Meeting Zach Wasserman, CTO of Fleet Device Management, is like embarking on a technological journey that bridges two different worlds. As he candidly reveals his adventurous shift from California to beautiful British Columbia, his love for both places shines through. "The weather's better in California," he admits, but the lure of British Columbia, especially its 16+ hours of daylight just past the solstice, has captured his heart. The big move coinciding with the chaotic events of 2020 – starting a new company and relocating amidst a pandemic – added an extraordinary twist to his tale.

The story of Fleet is more than the technology it represents; it's the embodiment of modern workplace dynamics. Wasserman's pride in Fleet's globally distributed team of around 45 people across at least eight countries resonates with the spirit of our times. "This company is really a child of COVID," he says, emphasizing the absence of physical headquarters. His journey from a "lone wolf" consultant to a hands-on leader who works with everyone in the company exemplifies the transformative power of collaborative leadership.

Perhaps the most intriguing part of Wasserman's leadership philosophy is his insight into what makes a true leader. Noting that inspiration and motivation have always been his forte, he pinpoints the real challenge as aligning different people towards a common goal. It's a nuanced, refreshing perspective that speaks volumes about his growth as a leader. His best quote from the conversation encapsulates this beautifully: "Leadership for me is not so much about inspiring people, it's about figuring out how to get so many different people pointed in the right direction." In a world where leadership is often reduced to mere buzzwords, Zach Wasserman offers a lesson in authenticity and hands-on management, grounded in his own unique experience.

From Facebook's Glory Days to Fleet: Zach's Journey of Innovation, Open Source, and Entrepreneurship

Zach's time at Facebook, a whirlwind experience that lasted just a little over a year, turned out to be more than just a stint at a big company. It was a gateway, a catalyst that shaped his entire career. Recounting the days of working with the tech giant, he recalls the "glory days of Facebook," a period of brilliance filled with innovation and open source commitments. One of his crowning achievements at Facebook was co-creating OS query, a security project that was allowed to thrive in the open source environment.

But Facebook was just the beginning. Tired of a structured office life, Zach left the company to forge his own path. Building on the foundations laid at Facebook, he plunged into consulting and entrepreneurship. Through his work on OS query and other ventures, he eventually started Fleet. Zach's narrative is an inspiring journey of self-discovery, exploration, and growth. It's a story of recognizing opportunities, seizing them, and turning them into a force of change.

Zach's belief in the power of open source reflects a philosophy he inherited from Facebook. The company's foresight to invest in open source attracted brilliant engineers and led to the creation of lasting projects. In Zach's words, the most resonating insight: "They realized, if you invest in open source, you can attract some of the best engineers out there… it makes no threat to your competitive advantage. Like as a social network, you can release security tools for free, and it's not going to affect your moat there." This thinking has driven his entrepreneurial journey, cementing a legacy that continues to inspire and challenge the tech industry.

A Blind Date with Success: Zach’s Unconventional Journey from a Chance CEO Meeting to Co-founding Fleet

In the midst of a global pandemic, when chance encounters were rare and fleeting, Zach found himself at a life-altering crossroad. It was a CEO from GitLab who reached out to him with an opportunity that felt like a "blind date." He was offered guidance and support for his technical work, a pitch that resonated with Zach's passion for focusing on the technical side rather than the pure business angle. This connection led to a co-founding partnership with Mike McNeil, a relationship nurtured and developed entirely online for over a year. "I just had a good feeling about the whole situation," says Zach, reflecting on this unexpected opportunity.

Starting a business with someone you've never met is a leap of faith, and Zach's story is a testament to that. It's not merely about making it work; it's about crafting a harmonious relationship from a blank canvas. Zach believes that this blank slate was not a disadvantage but an opportunity to be really open and transparent from day one. "I think that it gives you the opportunity to start from day one being really transparent and really open with your communication," he explains, emphasizing the importance of honesty and regular reflection to ensure a successful partnership.

Zach's journey wasn't just about seizing an opportunity; it was about managing risk and aligning his path with his passions. When asked about the difficult decision to leave his previous startup for Fleet, he sees it through the lens of risk management. "Well, what was the risk as giving up maybe the opportunity to be part of this thing, but it wasn't really what I was super excited about. And the risk was like, well, I could keep working on the thing I was excited about, and it wouldn't work out. And then I'd have to get another job. So, I think it's the kind of risk that was very manageable," he reveals. This pragmatic yet daring approach has guided him through the highs and lows of the entrepreneurial journey, cementing his position as a thought leader in the field.

Merging Security & Innovation: Zach's Vision of a Unified Tech Frontier

The world of technology is a playground for the future, and as we see a rise in the realms of artificial intelligence and machine learning, the concept of security must evolve alongside it. Zach, the visionary behind Fleet, a company that builds software to help other organizations manage their security, is a fascinating figure in this new era. In an eye-opening discussion, he paints a picture of a world where IT and security aren't isolated chambers; they're integrally interwoven. "I think that people are realising that, in order to do either of these, it has impacts on the other side of that, and so starting to kind of merge those teams is a trend that we're going to see more and more," he explains.

Zach's reflections aren't limited to the tech field; he speaks from the core of his journey as an entrepreneur and innovator. He addresses the overnight success myth and emphasizes that building something meaningful takes time, persistence, and a readiness to embrace the grind. "Each day, when things are hard, you just keep going, because that's how you get somewhere," he confides, with an air of wisdom and hard-earned experience.

Finally, Zach's enthusiasm for what lies ahead is not just about technology; it's a tale of human growth, team-building, and the realization of dreams. From being a "lone wolf" to leading a team of over 40 passionate individuals, his journey is about a vision coming to life. The joy, excitement, and synergy within his team and customers resonate with his unwavering belief in innovation and collaboration. It's not just about Fleet; it's a glimpse into a future where we are all connected, secured, and driven by a shared desire to transcend boundaries. And that's something that doesn't just excite Zach; it should excite us all.

Rusana Shkaraban

Podcast Host at Temy

Are you ready to peel back the layers and uncover the real story behind industry leaders’ success? As a Podcast Host and Writer at Bright Founders Talk, that’s exactly what I’m here to do. Whether the journey was smooth sailing or filled with bumps in the road, I’m here to get our guests to remove the smoke and mirrors and share their authentic experiences. We all have a story to tell, and my job is to get to the nitty-gritty of it all, picking their brains to reveal secrets to their success.