Inside the Network

Mark McClain: Winning as an incumbent at SailPoint in the age of AI

This episode of Inside the Network is unique because it is our very first show recorded live on the RSAC 2026 stage in front of security leaders, startup founders, and identity experts. For this episode, we had the privilege of sitting down with one of the most accomplished founders in cybersecurity, founder and CEO of SailPoint, Mark McClain. Cybersecurity is not an easy market to take a company public, and only the most successful founders have the opportunity to take a company public just once. Mark on the other hand has taken the same company public twice. He created the identity governance category from scratch, grew the company into a global identity security leader with more than $1 billion in ARR, over 3,000 employees, and customers across nearly half of the Fortune 500, took it public in 2017, private again with Thoma Bravo in a multi-billion-dollar transaction, and then back to the public markets in 2025. This episode explores one of the biggest questions in cybersecurity today: how do incumbents survive and win in the age of AI?  Mark shares how large cybersecurity companies think about innovation, disruption, and adaptation in a world that’s changing faster than ever before. We discuss whether incumbents can turn scale, distribution, and customer trust into long-term advantages, or whether AI creates the perfect opening for a new generation of startups to challenge established leaders.  Throughout the conversation, Mark reflects on the evolution of identity security from compliance tooling into one of the most critical security control planes in the enterprise. We dive into the rise of non-human and agentic identities, why traditional governance models are breaking under the speed of AI, and how companies like SailPoint are adapting to a world where identities can be ephemeral, autonomous, and operating at machine speed. We also talk about building startups in Austin versus Silicon Valley, lessons from taking the same company public twice, the realities of operating as both a public-company CEO and a founder, and what early-stage founders continue to underestimate about enterprise cybersecurity markets.  In closing, Mark shares candid advice for founders building in cybersecurity today: where startups still have a real edge, what markets are ripe for disruption, and why listening to customers remains the ultimate competitive advantage. You can watch the full video recording of this conversation on-stage at the RSAC 2026 Conference here: Inside the Network Live: Winning as an Incumbent in the Age of AI. [https://portal.onersac.com/link/share/library/DA7B32983AB845A894FBDBCE6FDAB423]

Christina Cacioppo: From Y Combinator to redefining trust in cybersecurity with Vanta

In this episode of Inside the Network, we sit down with Christina Cacioppo, Co-Founder and CEO of Vanta, the company that defined what is now known as trust management. What began as a scrappy effort to make SOC 2 less painful, has grown into one of the most important platforms in security and compliance.  Christina’s path into cybersecurity was anything but conventional. She started her career in venture capital, and then worked as a product manager at Dropbox, where a frustrating encounter with compliance requirements revealed just how broken security audits were for fast-moving product teams. In our conversation, Christina shares how that painful Dropbox experience led to Vanta, why the company’s earliest product was essentially a spreadsheet rather than software, and how doing things manually helped her team find product-market fit faster. She talks about her process of ideation before landing on the idea, the decision to let word of mouth drive the business forward, what Vanta got out of joining Y Combinator, and why it intentionally avoided raising large rounds of venture capital in the early years.  Christina offers a refreshingly honest look at leadership and scale. She discusses the hard lessons of hiring executives, the importance of defining company principles through real mistakes rather than corporate platitudes, and the challenge of moving upmarket without abandoning the startups that made Vanta successful in the first place. Christina explains how competition changed her perspective on storytelling, why founders cannot let others define their narrative, and how much of company-building is really about learning on real people in real time. This episode is full of hard-earned lessons on conviction, clarity, and the long game of building a multi-billion-dollar company.

Sanjay Beri: Playing the long game and building Netskope into a public cybersecurity powerhouse

In this episode of Inside the Network, we sit down with Sanjay Beri, Founder and CEO of Netskope, a company that sits at the intersection of AI, data security, and global edge networking. Over thirteen years, Sanjay scaled Netskope to 4,000+ customers (including 30% of the Fortune 100), 3,000+ employees across 30 countries, and ultimately took the company public in September 2025 in one of the year’s standout cybersecurity IPOs. Sanjay’s journey is a masterclass in playing the long game. From growing up in Canada selling door-to-door with his mom, where he learned grit and resilience, to working at Microsoft during the early internet era, to becoming one of Juniper’s youngest VPs running a large business, Sanjay built the rare blend of product, go-to-market, and leadership muscle it takes to build at scale. We talk about the origins of Netskope, why it was never “just a CASB,” how Sanjay recruited world-class early engineers and built a high-trust culture, and what product-market fit looked like in the first chapter of the company. He also breaks down some of Netskope’s biggest bets, including building its own edge cloud instead of relying on public cloud networks, and launching AI Labs years before today’s GenAI wave. Whether you’re building a cyber startup, scaling into the enterprise, or studying what it takes to go from zero to IPO, this episode is packed with hard-earned lessons on conviction, the importance of building a winning culture, and endurance.

Dino Boukouris & Sam Bronstein: How AI, identity, and cloud security defined 2025 and what 2026 holds for founders

In this special year-end episode of Inside the Network, we’re joined by two of the most trusted strategic advisors in cybersecurity - Dino Boukouris, Managing Partner at Altitude Cyber, and Sam Bronstein, Partner at AXOM Partners. Between them, they’ve worked on billions of dollars in cybersecurity M&A, helped founders navigate exits to the world’s largest tech companies, and advised the CEOs behind some of the biggest public and private deals in the industry.  In this episode, which also happens to be the 20th episode of Inside the Network, we break down what really happened across the cybersecurity landscape in 2025, from customer buying patterns and budget constraints to the $96B in M&A deal volume. Dino and Sam share insights on what’s driving consolidation, how buyers think about valuation and timing, and what defines a hot company in 2026 (hint: it’s not just growth).  We talk about how mega-deals like Wiz and CyberArk are reshaping competitive dynamics in the industry, why SASE, identity, and security for AI have been the most active M&A themes, and what founders need to understand about building relationships with buyers long before they’re ready to exit. Sam and Dino explain that founders who achieve the best outcomes usually build relationships with potential acquirers over many years, and break down why many late-stage founders are likely to choose acquisition over IPO in the coming cycle. We close with tactical advice for founders heading into 2026: how to think about your board and investors, what metrics you’ll be judged on, and how to align your capital strategy with your long-term goals. And yes, we also talk about race cars, zero interest rates, outcome-based pricing, and what Palo Alto Networks might buy next.

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.