Proofpoint Protect 2026 | Molly McLain Sterling, Proofpoint

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Molly McLain Sterling

Senior Director, Cybersecurity Strategy

Proofpoint

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play_circle_outline Top customer worries: AI guardrails, visibility, and business enablement shift

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Molly McLain Sterling, Proofpoint

Molly McLain Sterling

Senior Director, Cybersecurity Strategy Proofpoint

In this interview from Proofpoint Protect 2026, Molly McLain Sterling, senior director of cybersecurity strategy at Proofpoint, joins theCUBE's John Furrier to discuss how security strategies are evolving as AI agents become embedded in everyday enterprise workflows. Sterling, who came to Proofpoint as a customer, explains why organizations are shifting from caution to action, establishing guardrails and clarifying agent intent as AI takes on more autonomous tasks. She notes email remains the top attack vector, with phishing messages growing harder to spot as... Read more

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What should customers do right now about AI-related security risks; where do they currently stand in terms of readiness and confidence, are they making progress, and how has the C‑suite’s role changed in responding to these issues? add

What trends are you seeing in email-based threats, how is AI changing their sophistication, and what detection challenges does this create? add

What are the top three concerns among Proofpoint customers and prospects right now? add

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Molly McLain Sterling, Proofpoint

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John Furrier

>> Palo Alto studio, connecting, Silicon Valley and Wall Street. I'm John Furrier, the host of theCUBE here with Dave Vellante, my co-host. I'm John Furrier with theCUBE. We are in San Diego for theCUBE and the NYSE Wired program and Open Community for Proofpoint Connect 2026. This is a conference bringing together security professionals in the industry to talk about how security in the enterprise is shaping out. Molly McLain Sterling's here. She's a senior director of global cybersecurity strategy at Proofpoint. Molly, thanks for coming on kicking off theCUBE and NYSE Wired here in San Diego.

Molly McLain Sterling

>> Absolutely, thanks for having

John Furrier

>> me.

>> So I'm really looking forward to this conversation because you were a customer and this seems to be a trend, I have to admit. You have a lot of customers come work for Proofpoint.

John Furrier

>> Yeah.

>> But also you're involved in strategy, you're also involved in a lot of the customer executive meetings. Also you are leading the Women in Cyber here at the event, which is booming. You're seeing a lot out in the marketplace. So I guess the first question is, being a customer now, being on this side of the table, what is the sentiment of the current customer base now? Because there's enthusiasm for agentic AI automating SOCs. We're seeing the trends, but then they also see all the AI for the bad guys too, right? So there's a lot more phishing. My emails have great spelling, great English. Yeah, I don't know what to click on. There's a lot going on, right? What's— where are the customers at right now? Where are they? Are they confident? Are they getting there? What's your perspective?

Molly McLain Sterling

>> First advice, don't click. Don't click on anything. I think overall for most customers, what we're hearing is there's cautious optimism. There are fears, there are concerns about what it can do and how fast it's moving. But it's also just such a revolutionary time for everyone that they're excited to be on the cutting edge and use it to be able to defend against the bad actors. So I think that's the biggest piece. Jokingly, I think I've heard some CISOs say they just want to retire and not have to deal with it.

John Furrier

>> It's interesting. One of the big things we're seeing is that, in this typical security industry, it was always RSA, Black Hat, a lot of great products coming out. A lot of tools, moves to platforms. Now with AI, you're starting to see a lot more interaction with the C-suite because again, that brings in the human resources, maybe potentially the CFO looks at the business cases, looks at potentially the risk management side of the posture. How have the customers evolved to not just putting this in the lap of the CIO or the CISO? Yeah. How has the C-suite changed? Are they thinking, are they working together? Is it Don't tell me the bad news, only give me the good news. what is the current— because this is— I haven't seen this before.

Molly McLain Sterling

>> Right. I think every organization is different, but the one common theme with all of the organizations is that they need security to be business enablers. So, I think that's the difference. Before, you might have had some organizations where the security organization or the security office got to be the office of no, if you will. Now, they are really being pushed to say, Okay, we're gonna use AI, how are we gonna use it safely?

John Furrier

>> On the agent side, which is the big buzz, well, coding has been great. I mean, we've seen that with coding. I was talking to an engineer and a SOC engineer in cyber, they're like, this has actually been great for us. We could use AI too. So there's two sides of the AI coin. The bad guys have it and the good guys have it too. So the real rush on that, but the human piece comes down to it. Now it spawns multiple conversations. Who owns the agents? Where's the traceability? Yes, I want to make sure it's explainable. Then you've got more on the how do I make it a better feature for me, the SOC manager or someone in security. So the human piece is key. How does that come out in conversations with customers?

Molly McLain Sterling

>> You know, I think with customers, one of the main things that I try to bring up with them for the human piece, whether it's actually humans or agents, these things go together really clearly. Is intent. So really identifying what the intent is for the agent or the human actually is the most critical thing. And people are close to it, but they haven't quite nailed it yet because you can have an agent, you can give an agent a job and you think that they're going to do what you want them to do, but they optimize in some way where they're doing something totally different. So I think that's the key piece that humans and tech need to come together and figure out. And that's where you're going to find success.

John Furrier

>> Yeah, we've on theCUBE and SiliconANGLE, we've been covering all, obviously the security vertical with the NYSE Wired, we're looking at more of the impact to Wall Street, but also money, stuff, you see the CFOs coming into the conversation. There's a huge quantification around security, obviously no one wants to get hacked. They can tie that to cost. Now it's revenue also, if they can keep the bad guys out, that keeps operations flowing. How has that Agentic piece kicked in and what are people doing today as you guys look, to your customers because email was the first area that people attacked with phishing. We've all seen that. Now that you got the agents out there, what are some of the conversations you're seeing around how do I manage this properly and how and what's the biggest change from, say, 12 months ago?

Molly McLain Sterling

>> Yeah, so many of the threats, majority of the threats are still coming through email and we are so fortunate to have such a large customer base. So we see all of that data coming in. And we're able to see whether it's AI, whether it's humans, we're able to analyze those things. We're definitely seeing that, like you said, the emails are more perfect. they're in different languages perfectly. The branding is perfect. So a lot of it comes down to, again, that intent and being able to try to figure out, does this seem right in this particular scenario? I think that's the biggest thing that we've seen really push forward. Also, just with people's use of AI, they're starting to allow agents to do things on behalf of them rather than just chat with them. that's okay.

John Furrier

>> So I guess my follow-up question to that would be, okay, we're seeing transformation now happen with AI at many levels, not just IT or tech. Yeah, there's business model. What's been the velocity? Because you're seeing machine speed, got agents out there, fleets of agents. What's been the velocity and what's been the biggest change management discussion with security? Obviously, Microsoft has gotten a lot of attention.

Molly McLain Sterling

>> Yeah, yeah.

John Furrier

>> What else is out there? What's been the big change this year in terms of the velocity around how people are changing how they do business?

Molly McLain Sterling

>> Right. Well, I think security is no longer on the patching clock. You can't patch your way to being safe because they're going to find them faster and faster and faster. Zero Day Clock is estimating that vulnerabilities will be found every minute by 2027. So you're not going to be able to patch fast enough.

John Furrier

>> So Patch Tuesday is dead.

Molly McLain Sterling

>> Can it be?

John Furrier

>> You know, it's gone. Patch Tuesday is Patch Minute.

Molly McLain Sterling

>> Yeah. Patch minute basically is where we're at. So you really have to be protected in between. So you need those layers. It sounds like what we've been talking about from the past, but it's so much more important now to have those layers of defense as you go along.

John Furrier

>> Talk about the reskilling and upskilling, 'cause it always comes up every year, but now we're seeing superpowers come in. AI's giving people beyond Copilot capabilities now. I have it integrated into my email, I got a chief of staff agent, I got my flights changing around, I don't want a middle seat. It's already kind of happening.

Molly McLain Sterling

>> Yeah.

John Furrier

>> How has the job changed from upskilling, reskilling, the stuff that people need now. They don't teach that at school. Some of the things going on, what's the makeup of success look like from an individual? What's the skilling? Take us through the job situation.

Molly McLain Sterling

>> Yeah, it's an interesting time. I think it's a time that I haven't personally, at least in my life, seen before. And I think the soft, as they say, soft skills are really coming forward as something that is important. But they were always important. I think it's just now they're coming about. One of the things that I'm really excited about here, you mentioned at the beginning, is Women Who Cyber. We're hosting a big workshop for that. And what we're doing there is just talking about how AI produces so much noise and how do you find the signal in the noise. And I think that's part of the equation for people's success individually and companies as a whole is how do you block out that noise of all the AI junk and focus on what's really important, what are the skills that you need to learn?

John Furrier

>> Talk about the Women in Cyber that you guys do here at Proofpoint, because women in cyber in the security industry is growing. They have, every event has it. What are you guys hosting here? Take us through the group. How big is it? How fast is it growing? And what are some of the cool things going on?

Molly McLain Sterling

>> So Women in Cyber at Proofpoint is so close to my heart. I could talk about it forever, but it's a huge group. We've had thousands of people participate in it for many years, nationwide, worldwide. here at Connect, we're having a workshop, so it's a half-day event. Last year we had, 40% male, 60% female. So it's really— it's all-inclusive. This isn't just a girls' club kind of thing. Everybody can come. And what we're doing is talking about the work itself. So while it's important to talk— for women to talk about their experiences as a woman in cyber, it's more important, at least in my view right now, to talk about the work itself and all of the cool stuff that they're doing. We have a threat researcher that's going to give a demo. We're doing a really interactive table talk. So things that are really meaty and anybody can learn from.

John Furrier

>> Yeah, one of the things you bring up there, I'm thinking about that, is that the tabletop and the mix of personnel in these teams is the teamwork equation is changing. Again, this is another observation from our many events we go to with theCUBE is that the silos— yeah, people say they're breaking down the silos, but at the end of the day, there's still always silos. There's little pockets of groups.

Molly McLain Sterling

>> Yeah.

John Furrier

>> This has always happened kind of in the male-dominated piece, but put that aside for a second. But just when you start having agents, you have cross-domain activity, a lot more teamwork is surfacing. Can you share your thoughts on if that's coming up on the radar? We're seeing people actually care about other people's roles, data's being shared. cyber's always been a data-sharing culture, but specifically the teams, how have you seen the team construct change or the dynamics?

Molly McLain Sterling

>> This is such an interesting thing that I've witnessed because there's a particular thing that we have, it's called Threat Flip. And in my experience, I've done a lot of work in security awareness and the CSIRT and the security awareness teams, usually never talk or it's very rare in companies. These are wildly different, typically, types of folks.

John Furrier

>> Cats and dogs living together, kind of thing going on.

Molly McLain Sterling

>> Right.

John Furrier

>> But they didn't have to in the past because they had their— unless they had meetings.

Molly McLain Sterling

>> The smart ones did. So I thankfully had an amazing CSIRT partner when I was in previous roles and we found great benefit to be able to talk to each other, but we did it manually. Now that there is technology there to be able to break some of those silos down so that they have this common language that they can speak to. So I think that's a really exciting part about it. It's almost translating between the two groups in a language

John Furrier

>> that—

>> So you see more teamwork

Molly McLain Sterling

>> then?

Molly McLain Sterling

>> Yes, I do,

John Furrier

>> yeah.

>> What are some of the cool things you've seen just anecdotally or observation, a data point? Talk about some of the coolest things that have come

Molly McLain Sterling

>> out.

Molly McLain Sterling

>> Yeah, again, that ThreatFlip piece because you have a threat that will come in or an email that comes in, it's really complicated and they'll look at the header information and all that type of thing and they can send it over to the security awareness team as an example that can then be used for a phishing simulation. So it's a real-world attack that came into the organization. It's very specific to that organization, but they're sending it to the security awareness team in just plain language. And so that they don't have to have the skills that they have. It's just this kind of beautiful symbiotic relationship now

John Furrier

>> that—

>> Yeah, and those tabletop exercises and all kinds of exercises like that help foster teamwork. Yeah. How does a Proofpoint customer or someone in the industry get involved with your group?

Molly McLain Sterling

>> Women Who Cyber? Yeah. There are so many people. Doing Women Who Cyber at Proofpoint. It's certainly not just me. I am lucky enough to be a part of it. It's on our website. There are events being hosted all over the nation all the time. So you can literally stumble upon it when you go onto our website.

John Furrier

>> What's on the agenda here in San Diego this year? What are some of the activities planned?

Molly McLain Sterling

>> Yes, we have the threat research demo. So that's going to be amazing. And again, our theme is the signal over noise. So how do you block out the noise? How do you focus on the signal that's important? There's no better way to do that than through threat research. they're looking for the needle in the haystack and that's a great one. We'll do a really interactive table talk. We have a partnership with ISACA, so we'll have some ISACA members and customers doing a panel talking about the amazing work that they're doing. So I'm so excited to be able to do it.

John Furrier

>> Well, that's awesome. Great work. Final question for you. As you look at the Proofpoint customer base and prospects, you guys do a lot of customer advisory work, boards come together, you have key customers that give you feedback. What's the top 3 things people are worried about right now when you have that meeting? If we had a meeting right now, what would we be talking about?

Molly McLain Sterling

>> Yeah, the guardrails for AI, making sure that they're appropriate and effective, making sure that they really have an idea of where AI is in their organization. I always say never underestimate an employee with a deadline and a credit card because they will go buy whatever they need to buy. And then I think just sort of the business enablement piece again, that they're needing to be a business enabler versus stopping something. It's a shift in mindset for a lot of them.

John Furrier

>> Well, Molly, thank you so much for taking the time to kick us off here in San Diego at theCUBE NYSE Wired. Appreciate it.

Molly McLain Sterling

>> Thank you.

John Furrier

>> All right. I'm John Furrier, host of theCUBE. We are here in San Diego, Proofpoint Connect 2026. Just having the accurate data, but also the teamwork. You're starting to see a lot more activity where Domains are being crossed by the data. The agents are out there, the code review, but it's also making people more productive. More content coming after the short break.