Dean Sysman: Betting on a boring problem and scaling Axonius past $100M ARR

In this episode of Inside the Network, we sit down with Dean Sysman, co-founder and CEO of Axonius, one of the fastest-growing cybersecurity companies in the world. From struggling with his first startup to building a category-defining unicorn valued at $2.6 billion, Dean’s journey is a raw, insightful, and unfiltered look into what it really takes to build in security.

Before founding Axonius, Dean co-founded Cymmetria, a Y Combinator-backed deception startup that despite all the efforts, didn’t end up leading to a successful outcome. That experience didn’t stop him; it made him more grounded, more strategic, and more deliberate. Dean 2.0 didn’t enter a hot market. Instead, he went after a boring but foundational problem everyone had, but no one wanted to touch - cyber asset visibility. In just under five years, Axonius surpassed $100M in ARR and raised over $600 million to fund growth and acquisitions.

Dean’s path has been unconventional from the start. He taught himself to code at 12, won an international robotics competition at 15, and led a team in Unit 8200 by 21. In the military, he learned responsibility the hard way: “If you fail, no one else is coming to help.” That mindset became the core of his entrepreneurial approach. In this conversation, Dean opens up about what most people get wrong about Unit 8200, why the army’s bureaucracy actually helped him understand enterprise sales, and how he turned a failed venture into the insight that led to Axonius.

We talk about the early days of building Axonius, the decision to go deep into a “Toyota Camry” problem, and how he convinced two close friends from Unit 8200 to bet on a boring idea that became a unicorn. Dean breaks down the evolution of cyber asset management, what it took to define a new category, and why timing and value communication matter more than tech novelty. He also shares lessons from Axonius’ first acquisition, Cynerio, and what founders need to understand about getting M&A right: culture, timing, and strategic alignment matter far more than valuation spreadsheets.