From Y2K to AI: Jake DeWoskin’s 31-Year Adventure in Cybersecurity 

In line with Echelon’s value of People with Personality, we are excited to continue our Cybersecurity Champion series, where we spotlight the incredible individuals who make up our team. Each month, we share the stories of professionals whose talent, dedication, and unique perspectives help keep organizations secure. 

Meet Jake DeWoskin, Cybersecurity Manager at Echelon. With over three decades of experience, Jake’s journey has spanned the Y2K era, the evolution of cloud infrastructure, and today’s AI-driven threat landscape. Through it all, he’s remained motivated by curiosity, adaptability, and the drive to reduce risk in a rapidly changing world. 

1. What initially drew you to cybersecurity, and how did that lead you to Echelon?  

Jake: I started my consulting career during the Y2K era. What fascinated me was the uncertainty; people were predicting planes falling out of the sky or ATMs spitting out money. When nothing catastrophic happened, it was largely due to the thousands of engineers and developers working together to minimize risk. 

I began as a network engineer designing data centers, but as the cloud grew, infrastructure became commoditized. Security, however, was full of unknowns. I’ve always seen myself as a “hobbyist hacker,” and cybersecurity fits perfectly with my sense of adventure. Every day brings something new to learn, and that constant evolution keeps me motivated. 

I was drawn to Echelon not just for the talent here, which is incredible, but because it was the first company I’d seen explicitly state that cybersecurity and privacy are fundamental human rights. That alignment was powerful to me. 

2. Are there any cybersecurity trends or emerging technologies that you're particularly excited (or concerned) about, and why? 

Jake: AI and quantum computing are fascinating but also concerning. They represent innovation, but they’re also tools for criminal actors. What worries me even more is the education gap. Many adversary nations have prioritized developing “cyber warriors”, while the U.S. has fallen behind in producing the next generation of high-tech professionals. That systematic issue is one of the biggest risks we face.  

3. With nearly 31 years of experience, how has your perspective on risk management and network security evolved? 

Jake: I’ll never forget being on a help desk in the early ‘90s and overhearing executives say email would never replace fax machines. They thought the facsimile was the pinnacle of innovation. I remember thinking, “I think you’re wrong, this internet thing has legs.” 

Looking back, I feel fortunate to have played even a small part in building the global communication and economic engine we now depend on. For me, the biggest change has been seeing cybersecurity move from an IT function to a central part of corporate missions. I’ve helped build it, shape it, and now I help secure it; that’s a satisfying journey. 

4. What's one piece of advice you'd give to someone aspiring to get into cybersecurity today? 

Jake: Don’t chase traditional mastery, chase adaptability. In fields like accounting fundamentals, never change. In cybersecurity, they change constantly. The technology evolves, the threats advance, and the fundamentals shift. My advice is to embrace the unknown. Don’t fear it. Use it as motivation to keep learning, to challenge yourself, and to evolve alongside the industry. 

5. Are there any specific resources, books, blogs, websites, or communities that have been particularly helpful or inspiring in your cybersecurity journey? 

Jake: My biggest resource has always been people. I’m a hands-on learner, and I get the most out of collaborating with talented coworkers and peers. Cybersecurity is a team sport; you’re only as good as the people you surround yourself with. At Echelon, I’ve had the privilege of working with some of the smartest, most capable professionals in my career. 

6. What’s something you’ve really come to appreciate about being part of Echelon? 

Jake: The mission and the people. Echelon doesn’t just say cybersecurity and privacy are human rights; they live it. And being surrounded by such a talented team makes me better every day. 

7. Outside of work, how do you like spending your time? Any hobbies or interests that you’re passionate about?  

Jake: I grew up traveling, born in Japan, summers in China, and journeys across Europe, the Americas, and the U.S. That sense of exploration is part of who I am personally and professionally. Cybersecurity is often an adventure into the unknown, and travel gives me that same thrill. 

I’m also a father of two, which has been an incredibly humbling and rewarding experience. Beyond that, I’m a bit of an adrenaline junkie, I have a collection of fast cars, recently took up longboarding at 50, and I’m a big Formula One fan. I admire the precision and teamwork in racing; it’s a lot like cybersecurity. 

I also love cooking and doing my own car and home projects. There’s a sense of dependence that comes with knowing I can fix things myself. 

8. What does being a Cybersecurity Champion mean to you? 

Jake: Early on, cybersecurity had a kind of mystique, a cloak-and-dagger feel. Today, it means something much more important: standing for the belief that cybersecurity and privacy are basic human rights. When I saw Echelon embrace its mission, it resonated deeply for me. For me, being a Cybersecurity Champion means aligning my professional work with my personal values.