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Roland Cloutier reposted thisRoland Cloutier reposted thisEvery control we run was built under the assumption of human consequences. Underneath the policy docs, reviews and councils, governance relies on one basic thing: punishment. If we don’t comply? We can be fired. We can be sued. We can have our careers and reputations ruined. In the worst cases, we can go to prison. Approvals, audit trails, segregation of duties, the whole stack rests on one fact: a human is behind this, and that human has something to lose. Now look at the AI agents we’re building today: we give them names, job titles, a seat on the org chart. We model them after real people and real roles. This makes it easy to assume they arrive with everything a person does. They don't. And it backfires: in a 2026 study of 1,200+ managers, calling AI an "employee" instead of a tool dropped their personal accountability for its work by 9 points. An agent has nothing to lose. You can't fire it. You can't sue it. You can't shame or jail it. A few years ago Air Canada argued its chatbot was its own legal entity, a tribunal didn't buy it and held the airline liable. The law gets it right: it routes the liability to you. But our legacy governance models don’t account for this new, autonomous AI actor. And this is just the beginning. Whether it’s agents pushing changes into prod, making payments, operating in customer environments, doing consumer care… we’re only in the first inning of autonomous agents taking consequential, irreversible actions on our behalf. The people whose whole job it is to price risk already see it. Earlier this year, major carriers, Chubb, Travelers, Berkshire, etc., got approval to write AI exclusions into their policies. Others (Berkley, AIG, Great American, etc.) went with "absolute" exclusions that can strip coverage for those who fail to oversee their AI. It’s a whole new ballgame. The protections behind D&O and E&O are being carved out exactly where AI governance fails. We knew the risk was already moving onto our balance sheets, but now it’s onto directors and execs personally. And the accountability a person brings in the door for free? We now have to engineer it for agents ourselves: enriched identities, human owners, observability, evals, sandboxing… and that’s just the start. But the real work comes before any tooling. It's a governance call you make on day 1: who owns the outcome when the agent acts, what risks are we accepting, and can we defensibly prove both later? You need those answers before deployment of any kind. So pull your D&O and E&O policies and see what's already excluded for AI. Pressure-test the controls you'd lean on when things go wrong. And don’t govern machines with a model built for flesh and blood. We either build that accountability in now, or we answer for its absence later, with our own names on it.
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Roland Cloutier reposted thisRoland Cloutier reposted thisDo you like hard work? Do you like beating the bad guys? If you answered "yes" to both of those questions...I may have a place for you on my team :) (Note: please check the location requirements for the role before reaching out. This is NOT a remote position) https://lnkd.in/gfy6firVVice President, Cyber Governance, Risk & ComplianceVice President, Cyber Governance, Risk & Compliance
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Roland Cloutier shared thisLast night was the first in my nationwide dinner series for Shift to AI and what a great night with some amazing practitioner-leaders in New Jersey! This is quickly going to become my favorite event to host: we pick a city to go to , I gather a handful of exceptionally passionate, smart, and dedicated security, risk, privacy, and resiliency leaders for dinner, and we share, trade ideas, talk through hard issues, figure out how we can help each another, and create a better community. Huge thanks to my guests for joining: Christian Adam - Security Executive Wells Fargo Kim Albarella- Global Head of Security TikTok/ByteDance Ramachandra Hegde - CISO Genpact Tammy Klotz - CISO Trinseo Brian Lozada, CISSP - SecurityExec -Amazon Global Media, Entertainment, and Advertising Tim McKnight - CISO Merck Bill O'Connell - CSO Commvault Donna R. - CISO Radian Next stop is back to my New England roots and Boston! If you are in the Boston area and know someone I should meet, let me know. I’m making a list 😁 #cybersecurity #CISO #CSO #leadership #ShifttoAI #community
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Roland Cloutier posted thisWe're nearly full for the June 24th Shift to AI CISO dinner in Morristown, NJ with Cycode. Two weeks out from our first dinner in this series and I have to say - the conversations that are already happening on what the Shift to AI actually means for us before we even sit down are exactly why I wanted to do this. When you bring the right people into the room, the dialogue starts well before the dinner. Having longtime peers like Tim McKnight in the mix - who has lived this at the highest levels and now sees it through the lens of where security is heading - makes that even more true. And if you know someone in the Morristown / northern NJ area who belongs in this room, there may still be a seat. Drop names in the comments or tag someone directly 🙏 #cyberleadership #definingthefuture #CISO #CSO #secureAI #securingAI #businessoperationsprotection
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Roland Cloutier shared thisWise words from Tomás Maldonado. Operational outcomes aren't measured on luck, they are formed from proper preparation..... have a read. #cybersecurity #leadership #ciso #businessoperationsprotectionRoland Cloutier shared thisWhat Does Scuba Diving Have in Common with Cybersecurity? This past week, I had the opportunity to dive alongside my son, JeanCarlo, as he earned his Open Water scuba certification in the Cayman Islands. We averaged two to three dives a day and explored some incredible sites together. We also shared the stage at the DESCENT \\ CYBER Conference during a fireside chat and I had the opportunity to share my experience in cyber, securing big events, and leading through the era of Ai. As a father, it was a special experience. That said, as I reflect on the week, I keep coming back to one thought. Whether you’re learning to dive or leading through uncertainty, confidence doesn’t come from being fearless. It comes from preparation. Before every dive, there are equipment checks, planning, communication, and an understanding of the environment. The same is true in cybersecurity. The successful outcomes are often the result of preparation long before the moment arrives. What made the week especially meaningful was watching the next generation build that confidence for themselves. Not because someone told them they were ready, but because they put in the work to become ready. That lesson applies far beyond scuba diving. As leaders, parents, mentors, and teammates, one of the greatest gifts we can give others is not confidence itself. It is helping them build the skills and experience that confidence comes from. What lessons from outside of work have shaped your approach to leadership? #Leadership #Cybersecurity #GrowthWhat Does Scuba Diving Have in Common with Cybersecurity?What Does Scuba Diving Have in Common with Cybersecurity?
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Roland Cloutier shared thisThis was a great event with an amazing panel! Looking at how CISO's and Venture can work together for advancing the protection of next generation technology and your business's operating cyber defense.Roland Cloutier shared this💡 Where is venture capital investing in cyber innovation - and what does that mean for CISOs? This was the focus of “Follow the Money: Funding the Frontier” at ISTARI’s Compass conference in London last week. Paladin Capital’s Nazo Moosa shared her perspective on the evolving relationship between investors and security leaders, highlighting the need for strong feedback loops between CISOs and VCs. 🚀 As innovation accelerates, particularly in the era of AI, CISOs are often navigating uncertainty around what’s coming next, while investors are working to anticipate future risks and opportunities. Bridging this requires both a top-down and bottom-up approach: CISOs clearly articulating today’s pain points, and VCs “looking around the corner” to back the next wave of solutions. Engagement between operators and investors is essential to ensuring capital is directed toward innovation that truly matters. ⭐ Great to see Nazo contributing to this conversation alongside Grace Cassy (Ten Eleven Ventures) and Liran Grinberg (Team8), with Roland Cloutier moderating. Thank you to ISTARI for once again hosting a thoughtful and well-curated event. #investing #cyber #venturecapital
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Roland Cloutier reposted thisRoland Cloutier reposted thisStepping away from the ISTARI COMPASS summit, I am deeply energized by the caliber of discussions we had over the past two days.There is nothing quite like this #community coming together to tackle the hardest problems in cybersecurity, and it was fantastic to reconnect with so many friends and colleagues. A massive thank you to Rossa Shanks for the invitation. Your opening framing of the current challenges facing our industry—coupled with a deep, pragmatic optimism that our shared ingenuity will seize this moment and prevail—set the perfect tone for the event. A few standout moments that are still resonating with me: Azeem Azhar brilliant breakdown of linear thinking versus the exponential view. It served as a stark leadership agenda: our mandate is to outpace the curve, not just react to it. The highly insightful session with Tom Glocer , KC Yeoh , and Luca Kello which elevated the discourse around how we translate and manage cyber risk at the #board level. A great panel on improving the feedback loop between the VC ecosystem and the CISO community moderated by my friend Roland Cloutier with my two good friends Nazo Moosa and Liran Grinberg. Of course, a personal highlight was moderating our panel, "No Safe Mode: Governance at Machine Speed," alongside four exceptional leaders: Lisa Einstein ,Jonathan Lloyd White , Charles Ng , and Jonathan Dambrot . As we transition from #AI as a static productivity tool to dynamic transacting agents, our traditional oversight mechanisms are being pushed to their absolute limits. To embed #resilience at machine speed without throttling #innovation, we have to move past the illusion of deterministic control in probabilistic agent chains. A few of my favorite takeaways: 1)Shifting Accountability: We must move from asking "who pushed the button?" to "who mathematically defined the constraints?” 2)The Agentic Blast Radius Protocol: This must become a non-negotiable demand for boards. Before any autonomous system goes live, leadership must see mathematical proof of the worst-case scenario 3)Overhauling Non-Human IAM: Agents can no longer share static service accounts. We need dynamic, just-in-time, least-privilege credentials that expire the microsecond a task is complete. Looking toward 2030, I predict we will achieve a seamlessly governed ecosystem of autonomous agents—though it will likely be forged through the pain of a few high-profile failures first. We will build the right guardrails, but only after touching the stove. Thank you team ISTARI for an impecabbly executed event and for nurturing the collective intelligence of the community.
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Roland Cloutier shared thisLooking forward for this great discussion Nest Wednesday with Gabi on moving from cyber defense to cyber resiliency through operational readiness. As frontier AI compresses the time between disclosure and exploitation, security leaders need a more resilient approach to cyber risk, one that prioritizes what actually matters to the business. Join Gabi Reish, VP of Product Management at Bitsight and me for a live webinar on how to move from reactive remediation to cyber resilience. The focus of our chat will be : *Prioritize real risk, not just technical noise *Measure Operational Readiness with more defensible signals *Communicate security posture and capital risk reduction *Apply a practical four-pillar framework for continuous exposure prioritization and operational readiness If your team is still stuck in whack-a-mole mode and you are looking for how to be more operationally ready, this session is for you! Register Now :https://lnkd.in/eefuZsip #CyberReseleince #CyberDefense #OpsSec #BusinessOperationsProtection #Cybersecurity #CISO #CSO #RiskManagment #ABetterWay
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Roland Cloutier shared thisI'm returning to my old stomping grounds in Morristown NJ on June 24th to kick off a series of small, private dinners (small group, ~6 seats) for CI()SOs across the country with Cycode focusing on the shift to AI as operational security executives. The focus: a meaningful conversation on what the shift to AI actually means for us. Operationally. Culturally. Technically. Not a solution or vendor pitch - but the real conversation security leaders and our peers are having behind closed doors on leading through this amazing generational change. Can’t wait to see to see long time peers and partners like like my long time peer Kim Albarella and others who will be there! But here's my problem... there has been a lot of executive security movement in the Morristown / northern NJ area in the past few years, So who are the security leaders in the area I should be reaching out to? Drop names in the comments or tag someone directly 🙏 #CISO #ShifttoAI #securityleadership #aisecurity #globalsecurity #cyberdefensiveoperations #riskmanagement #securitycommunity
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Roland Cloutier liked thisRoland Cloutier liked thisEvery control we run was built under the assumption of human consequences. Underneath the policy docs, reviews and councils, governance relies on one basic thing: punishment. If we don’t comply? We can be fired. We can be sued. We can have our careers and reputations ruined. In the worst cases, we can go to prison. Approvals, audit trails, segregation of duties, the whole stack rests on one fact: a human is behind this, and that human has something to lose. Now look at the AI agents we’re building today: we give them names, job titles, a seat on the org chart. We model them after real people and real roles. This makes it easy to assume they arrive with everything a person does. They don't. And it backfires: in a 2026 study of 1,200+ managers, calling AI an "employee" instead of a tool dropped their personal accountability for its work by 9 points. An agent has nothing to lose. You can't fire it. You can't sue it. You can't shame or jail it. A few years ago Air Canada argued its chatbot was its own legal entity, a tribunal didn't buy it and held the airline liable. The law gets it right: it routes the liability to you. But our legacy governance models don’t account for this new, autonomous AI actor. And this is just the beginning. Whether it’s agents pushing changes into prod, making payments, operating in customer environments, doing consumer care… we’re only in the first inning of autonomous agents taking consequential, irreversible actions on our behalf. The people whose whole job it is to price risk already see it. Earlier this year, major carriers, Chubb, Travelers, Berkshire, etc., got approval to write AI exclusions into their policies. Others (Berkley, AIG, Great American, etc.) went with "absolute" exclusions that can strip coverage for those who fail to oversee their AI. It’s a whole new ballgame. The protections behind D&O and E&O are being carved out exactly where AI governance fails. We knew the risk was already moving onto our balance sheets, but now it’s onto directors and execs personally. And the accountability a person brings in the door for free? We now have to engineer it for agents ourselves: enriched identities, human owners, observability, evals, sandboxing… and that’s just the start. But the real work comes before any tooling. It's a governance call you make on day 1: who owns the outcome when the agent acts, what risks are we accepting, and can we defensibly prove both later? You need those answers before deployment of any kind. So pull your D&O and E&O policies and see what's already excluded for AI. Pressure-test the controls you'd lean on when things go wrong. And don’t govern machines with a model built for flesh and blood. We either build that accountability in now, or we answer for its absence later, with our own names on it.
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Roland Cloutier liked thisRoland Cloutier liked this🎙️ Podcast Preview: Preparing for the AI Vulnerability Storm It was a pleasure recording with Roland Cloutier and Phani Dasari today to discuss the #AI vulnerability storm (or is it a climate change?) . We bypassed the theoretical and focused entirely on the structural changes #cyber defenders need to make right now. Here's a teaser: #Architecture is the Ultimate Control: In a reality where machine-speed exploits arrive faster than teams can remediate them, your architecture becomes the control of last resort. Moving from Access Management to #OutcomeManagement: It is no longer enough to govern agents individually. We must manage emergent collective behaviors. Revaluing #Foundational Defense: Deep network segmentation, egress filtering, and disciplined identity management are not legacy hygiene; they are high-leverage controls that hold the line when prevention fails and patching cannot keep up. Leverage Your Home-Field #Advantage: While attackers rely on general knowledge to probe from the outside, defenders own the ground truth, the data, and the topology of their own environments. The winners will be those who claim this advantage rather than trying to outwork machines with human effort. Stay tuned for the release!
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Roland Cloutier liked thisRoland Cloutier liked thisCISOs and CSOs have deepfake attacks at the top of their minds. How will these attacks impact their top leadership, their credibility, and the organization as a whole? Ahead of the recent Gartner Security & Risk Management Summit, BlackCloak announced a full-category Digital Executive Protection Platform with a focus on our Impersonation Protection service. Founder and CEO Dr. Chris Pierson spoke with Digital Executive Protection Advisor Caitlin Jandrositz about this break-through feature, what security leaders are concerned about, and the increase in deepfake attacks. The team at BlackCloak is consistently innovating and adding features to better protect our clients. Stay tuned for more ways we're combating evolving threats in the coming weeks. Watch the full conversation: https://lnkd.in/e_8fGU2M
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Roland Cloutier reacted on thisRoland Cloutier reacted on thisThe best feedback I've gotten on Cranium AI's culture didn't come from a customer, a board member, or an investor. It came from a former intern last week. He pulled me aside to tell me his Cranium internship had changed the direction of his life. He's now pursuing business school on top of his technology work. He wants to build a company someday. He said the months he spent at Cranium showed him what's possible when you take real ownership early. I didn't have a clean response - it took me a second to receive this news. The thing about internships is that you never really know which ones are going to be formative for someone versus just a line on a resume. You hope. You (or more specifically your team - thank you Brooke, Kelsey, Gill, and the rest of the Cranium team!) - give them real work. You bring them into the conversations that matter. And then you let go. This summer's class of #Craniacs started a few weeks ago — five smart, curious, ambitious people who are now living their own version of that story. I don't know yet which moments they'll remember in five years. But I know this: the internship is never just about the internship. It's about giving someone enough rope to discover what they can build, and then watching them go do it. To the former intern who told me this last week — thank you. You had an impact on me too! #Internship #CyberCareers #AISecurity #BuildingTeams #CraniumAI #NewestCraniacs
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Roland Cloutier reacted on thisRoland Cloutier reacted on thisToday I launched Straiker's Series A. Career bucket list: ✅ officially checked. Ankur and I go way back, since our days together at RedLock. When he started building Straiker and came calling in early 2025 (before stealth launch ‼️ ), going all in was an easy decision. When most people were still asking "𝙝𝙤𝙬 𝙞𝙨 𝘼𝙄 𝙜𝙤𝙞𝙣𝙜 𝙩𝙤 𝙘𝙝𝙖𝙣𝙜𝙚 𝙩𝙝𝙚 𝙬𝙤𝙧𝙡𝙙?" I started seeing friends pick up Claude Code and build things. Developers shipping more and faster than ever, with AI as their co-pilot. Now I'm the one building agents to handle my own repetitive marketing work, getting 3-4x more done. But with every new agent and every new capability, the attack surface is widened. That's why Straiker's here. I knew this launch had to be felt, not just announced. We secured an Axios exclusive (shout to Shannon Van Every). Got the team on the Nasdaq tower in Times Square and filmed the founders video right there (Check out Ankur's page!). And we had investors who showed up like true partners: Lightspeed and Bain Capital Ventures (BCV) made the Nasdaq connection happen, Citi Ventures activated their own PR team to work alongside ours, Illuminate Financial and Rain Capital in the trenches on the weekend to amplify the announcement, Marathon Management Partners reached out to their media contacts and brought ideas that sharpened the whole launch. Getting there means you get sh!t done. Late nights, long weekends, rolling up your sleeves, working lockstep with leadership team. Fueled by love for this work and, honestly, by the belief that you can always do more than people expect. And then you stand in Times Square with the people you've been in the trenches with, and it all lands. Grateful. Proud. Excited. And just know there's more to come. 😉 Sreenath Kurupati | Chenxi Wang, Ph.D. | Yizheng Wang | Girish Chandrasekar | Parth Shah | Tessa Cohen | James A. Beasley | Allison Braley | Josh Machiz | Michael B. Gilroy | Gokul Rajaram | Jelena Zec | Venkata Sai Kishore Modalavalasa | Peter Hung | Phimm Phonpaseuth
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Roland Cloutier liked thisStarting and leading DataBee is a thrill and a highly rewarding challenge, that recently culminated in Gartner naming us in their Hype Cycle for Cyber Risk Management, as a sample vendor! This achievement represents nearly 4 years of persistence, optimism, creativity, vision, and positivity since our founding in late 2022, followed by an MVP in 2023 and fuller product in early 2024. Paul Kivikink and Lisa Croel with Erin Hamm have been the leading brains behind our Gartner briefings and the entire team has rallied behind them to provide the results necessary to make this possible. Thanks to everyone in the industry who has supported us and congratulations to my team on this incredible accomplishment in such a short period of time! You can read more about it, here: https://lnkd.in/epehRNau #womenintech #womenincyber
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