RSA Conference might grab the headlines with its 50,000-strong crowds and big-name keynotes, but for Steve Winterfeld, Advisory CISO at Akamai, the security calendar offers much more depth and value—especially for those willing to look beyond the marquee names.

“RSA has been around for over 30 years,” Winterfeld notes. “DEF CON has been around for over 30 years. Black Hat just under 30. So these are well-established conferences. But what really matters is aligning with your personal or organizational goals.”

While RSA, Black Hat, and DEF CON are essential gathering spots for security leaders and practitioners, Winterfeld emphasizes that the best conference for you might not be the biggest. “If you’re younger, more junior—go to B-Sides,” he advises. “If you’re a corporation—support B-Sides. That’s where we’re developing the next group.”

What makes B-Sides unique, according to Winterfeld, is its technical depth and accessibility. “Junior people have an opportunity to go speak. It’s a lot more technical in nature,” he says, highlighting its critical role in community building and mentorship.

Regional conferences also earn high marks from Winterfeld. “I’m a big fan of going to your regional conferences so you can make local connections and build out your network,” he says—an insight that resonates in an era of increasingly remote and decentralized work.

Vendor-specific and analyst-driven events (such as those from Forrester or Gartner) also play a role, depending on whether you’re looking to deepen tool-specific knowledge or gather cross-industry insight.

So, how do you choose?

“Ultimately, I think you’ve got to ask: Do you want to do better networking? Do you want to get your continuing education points? Or do you want to train on something specific to take action on?” Winterfeld suggests.

That kind of clarity is rare—and valuable. It cuts through the noise of flashy booths and sponsored keynotes, redirecting the focus to what matters: tangible outcomes, skills, and connections.

Whether you’re charting your professional growth, justifying a travel budget, or investing in your team, Winterfeld’s advice is worth bookmarking.