Alex Cunningham
Greater Boston
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About
I lead the strategic direction and execution of Advisor360°'s information security, risk,…
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3K followers
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Alex Cunningham posted thisI hate you - that's how I responded to our risk manager this afternoon over Slack after falling for my first ever phishing test today!! But wait, I have an excuse: I had just been alerted to a potential issue (which thankfully didn't materialize), I was still processing a phone call I had just come off of, and I was in the middle of a roundtable discussion with a group of really cool start-up firms. It really wasn't my fault..... And guess what? I'm sure if it had been real the bad actor who sent it to me would have been really sympathetic too.... Over the years I've participated in many conversations about the value of conducting periodic phishing simulation tests. My view has always been that they do have value and if nothing else serve as a reminder to "pause before you click," especially when you're on your phone and distracted. As a security leader it's just as important to pause and remind ourselves that none of us are immune to the tricks and tactics bad actors deploy daily and that our programs need to accommodate this. Today's lesson also reminds this security leader to practice what he preaches, emphasize the importance of security basics and empathize when others fall for this test. Thank you to my risk manager for reminding me of this valuable lesson - and maybe I hate you less now!!! :) #wenoti #cyberrisk #teamwork #riskculture #loveourriskmanager #cisolife
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Alex Cunningham shared thisA few of the Advisor360° team had the pleasure of attending the American Red Cross - Massachusetts 2026 Boston Heroes Breakfast this morning. The generosity shown was truly amazing and over $1M was raised! Congratulations to all the award winners and thank you for allowing us to participate at this amazing event! Jason Quinn Darren TedescoYossi Hazan Mike Fanning Chirag Patel #community #giveblood #wealthtech #innovation
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Alex Cunningham shared thisA strong cybersecurity program foundation is table stakes today regardless of the size of your firm and building it into your firm's DNA can be the difference between success and failure. Hope you find these thoughts helpful as you build your own program. #teamsport #wenoti #cyber #riskawareculture #businessoftrustAlex Cunningham shared thisCybersecurity is central to how wealth management firms earn and keep client trust. In his latest blog, Advisor360° CISO Alex Cunningham shares our approach to helping firms move beyond reactive compliance to a more proactive, resilient path to protecting client data. From data governance and auditability to third-party risk, firms that get this right won’t just stay compliant, they’ll stand out. Read the blog post: https://lnkd.in/e_YhAhua #Cybersecurity #WealthTech #RiskManagement #Trust
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Alex Cunningham shared thisCongratulations to the Advisor360° team for delivering more great innovation focused on making an advisors day to day operations easier, faster and more accurate. Stay tuned for what's coming next!! #teamwork #wenoti #letsgo #innovation #aioperatingsystemAlex Cunningham shared thisAdvisors shouldn’t have to toggle between systems to get work done. That’s why we’re excited to announce our new integration with CapitalROCK's RightBRIDGE®, bringing onboarding and compliance documentation into one connected workflow—reducing friction at one of the most complex points in the advisor workday. The impact is clear: faster account opening, fewer errors, and more time back for client relationships across MassMutual's network of financial professionals. - 15 minutes saved per account opening - 66% reduction in paperwork errors Read the full press release here: https://lnkd.in/eBmaGvwk #Advisor360° #MassMutual #CapitalROCK #AdvisorExperience
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Alex Cunningham posted thisUnlike last week I’ve managed to avoid Boston’s weather and heading to Tampa for Advisor360°’s FY-27 sales kick off event. Looking forward to aligning on our strategy, learning lots and having some fun with some awesome teammates! #sko #oneteam #winning #whitenight #orlysangels
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Alex Cunningham shared thisThank you BostonCISO for the nomination and congratulations to all the finalists. I'm sure my fellow cyber leaders will agree that without the stellar work their teams and firms do every day this recognition would not be possible. To everyone at Advisor360° thank you for everything you do to keep the A360 house secure while leading the way in wealth management AI innovation. #letsgo #wenoti #oneteamAlex Cunningham shared thisMeet the Finalists of the 2026 BostonCISO #ORBIE Awards | https://lnkd.in/giFWHfr2 Super Global Jasvinder Khera, John Hancock Christina Mazzone, CISSP, CIPT, CIPP US, Omnicom Group John Schramm, Munich Re Group Mark Sutton, Bain Capital Global Julie Fitton, Analog Devices Inc Stacey Fortin, Sensata Technologies Tyler Gilbreath, Bain & Company, Inc Satyendra Thakur, Hasbro, Inc. Large Enterprise Sam Curry, Zscaler Gael Frouin, AAA Northeast Eric Jacobsen, Boston University Christopher Kennedy, Group 1001 Robyn Ready, CISSP, CISM, PMP, Knitwell Group Robert S. Sherman, Lantheus Enterprise Erica A., Mercury Systems Stephen Danckert, Haemonetics Corporation Lorna Koppel, Tufts University Astrid Lambert, Cambridge Health Alliance Mike Nichols, CIRCOR International Matt Shaw, Southcoast Health Large Corporate Chris J Bernard, Ed.D, MBA, CISSP, CCSP, The Jackson Laboratory Brian Castagna, Rapid7 Benjamin Dulieu, Duck Creek Technologies Tom Kane, Boston Mutual Samir Sanghani, Coverys Julia (Starr) Chang, Flagship Pioneering Corporate Kyle Bubp, Avid Deborah A. Cafarella, Shields Health Care Group Alex Cunningham, advisor360 Michael Gioia - CISM, CISSP, Babson College Tim Holmes - MA, MS, CISSP, College of the Holy Cross Brian Landry, Cambridge Savings Bank Inspire Leadership Network Boston Business Journal Catherine Lorence
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Alex Cunningham shared thisThe rapid growth of AI continues with no end in sight. Enabling this game changing innovation safely is critical to every organization's success. Financial advisors continue to adopt AI but only when they trust it. Come see what we're doing at Advisor360° to enhance their experience. #aigovernance #advisorexperience #trust #innovationAlex Cunningham shared thisAI adoption is accelerating across fintech—but trust doesn’t scale on its own. As AI becomes embedded in daily workflows, governance is no longer optional—it’s foundational. In our latest blog, Advisor360° Chief Information Security Officer Alex Cunningham explores why AI Governance Committees matter, how they enable innovation (not slow it down), and how we approach responsible AI at scale. 👉 Does your fintech partner have an AI governance committee? Read the full post here: https://lnkd.in/e9iwWBym #AIGovernance #Fintech #ResponsibleAI #WealthManagement
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Alex Cunningham shared thisIt's great seeing this partnership go from strength to strength. Providing Advisor360° the ability to protect our organization and Harmonic Security with valuable real time feedback as they address a huge need in the market. #partnership #aigovernance #growth #teamwork #winwin #letsgo!Alex Cunningham shared thisExcited to see Michael Janielis and Advisor360° featured in Dark Reading for the work they’re doing to stay ahead of Shadow AI. They’ve been an incredible design partner for us, helping shape Harmonic into a product that actually solves real-world problems for security teams. You can’t build this kind of tooling in a vacuum. You need innovative, forward-leaning teams who are willing to engage deeply and move fast. That’s exactly what Advisor360 brought to the table. Check out the piece here: https://lnkd.in/dzaqTBBf
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Alex Cunningham shared thisAI has profoundly changed our relationship with technology and how we use it going forward. Advisor360°’s WealthOS is a true game-changer, setting a new standard for technology and benefits for advisors and their clients. #aiinnovation #exerprience #settingthestandardAlex Cunningham shared thisGreat conversation with Davis Janowski on where wealth management is headed. At Advisor360°, our focus is on the Advisor Experience, which we define as the end-to-end digital and human advisory experience. This encompasses not just front-end tools, but the entire journey for investors, advisors, assistants, and home office teams. What we’re seeing is simple: the future intelligent experiences can’t be built on fragmented infrastructure. That’s why our strategy is an AI-Native Wealth OS, a unified foundation that brings data, workflows, and intelligence together. Full Article: https://lnkd.in/eAuD2y2Y It was validating to see this direction echoed externally as #4 in The AI Corner’s a16z AI ideas for 2026 on rebuilding financial infrastructure around AI-native systems: "AI cannot fully transform finance until the infrastructure underneath is rebuilt". Full Article: https://lnkd.in/e_zaX_xB The future of wealth management isn’t more tools. It’s holistic, hyper-personalized advisor experiences powered by Wealth OS. #AdvisorExperience #WealthOS #AI #WealthTech #Advisor360 Mike Fanning, Mat Mathews, Alison Durant, Frank Pupo, Dave Parenti, Paul Morville, Alex Cunningham, Darren Tedescoa16z Partners Just Laid Out the AI Playbook for 2026a16z Partners Just Laid Out the AI Playbook for 2026
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Alex Cunningham liked thisAdvisor360° exists for one reason: the advisor. We support advisor choice and portability so advisors can make the best decisions for their practice and clients. Most advisor transitions require a full tech reset which causes major disruption - new systems, broken workflows, and a few months just getting back to baseline. That is why this news is so exciting. Advisor360° has been approved as a supported technology platform for Merit advisors, so advisors already on Advisor360° can keep everything as is - same workflows, same client experience, no rebuild. And, Advisors new to Advisor360 can experience a connected platform with an open ecosystem, unified data model, and AI-native architecture behind it. Super exciting! #advisorexperience #ria #advisorportability #fintech #aiAlex Cunningham liked thisGreat technology shouldn't have to stay behind when an advisor moves forward. We're pleased to announce that Merit Financial Advisors has approved Advisor360° as a supported technology platform, giving Merit advisors the freedom to run their practice on a connected, AI-native platform they already know and trust. For advisors joining Merit who are already on Advisor360°, this means zero disruption. Same workflows. Same client experience. Same platform—now fully supported within Merit's ecosystem. Great advisors deserve great tools. This is what that looks like in practice. Read the full announcement: https://lnkd.in/eu3B8-u5 #AdvisorExperience #RIA #AdvisorPortability #FinTech
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Alex Cunningham liked thisAlex Cunningham liked thisThe Sir Arnold Clark Summer Fund is back! We’re excited to share that the Sir Arnold Clark Summer Fund is now open and ready to support young people this summer! Arnold Clark has once again partnered with Cash for Kids West Scotland to provide funding for community groups and charities delivering projects for disadvantaged children and young people across Glasgow and the West of Scotland. Grants available: • One award of £5,000 • One award of £2,500 Applications are open until 22nd May, so don’t miss your chance to apply! Apply here: bit.ly/3OJAEch
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Alex Cunningham liked thisAlex Cunningham liked thisHis Majesty's Consul General David Clay MBE hosted a reception with UK climate tech companies during Boston Climate Week. The UK Government is proud to back the climate tech sector at every stage, with support from Innovate UK, Great British Energy, the British Business Bank, and the National Wealth Fund helping businesses start, scale, and succeed. Events like these reinforce the strong opportunity for collaboration between the UK and Massachusetts in driving clean growth. 🌎 Evan Carr, Jack Conway, UK Business and Trade - North America
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Alex Cunningham liked thisAlex Cunningham liked thisLooking forward to this panel on June 4th. Register to join us at the event! https://lnkd.in/enZfM8UHJoin us at the K logix CISO Leadership Series: AI Priorities for Security Leaders, to hear how top executives are navigating these challenges. We’ll discuss how AI amplifies existing risks, pressures… | K logixJoin us at the K logix CISO Leadership Series: AI Priorities for Security Leaders, to hear how top executives are navigating these challenges. We’ll discuss how AI amplifies existing risks, pressures… | K logix
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Alex Cunningham liked thisAlex Cunningham liked thisBlitzy Joins the Unicorn Club: $200M at a $1.4B Valuation Out of Cambridge Cambridge-based Blitzy announced this week that it has raised $200 million in new funding at a $1.4 billion valuation, officially making it Massachusetts' newest AI unicorn. The round was led by Northzone, with participation from PSG and Battery Ventures, and brings the company's total funding to more than $204 million in just over two years. For Massachusetts, it's another loud signal: the next generation of category-defining AI companies is being built in Kendall Square.
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Alex Cunningham liked thisAlex Cunningham liked thisI'm so excited to attend the CISO Dinner in #Bostonand! This event is complimentary for qualified CISOs and brings together local #cybersecurity leaders to participate in a round-table discussion on today's most tactical issues! Join me: https://lnkd.in/e9S2kkbs https://lnkd.in/eSB8TZiE
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Alex Cunningham liked thisAI has made security harder. That's not controversial — but what to actually do about it is where most organizations are still struggling. Next week I'm joining Rob van der Veer from Software Improvement Group for a conversation on cutting through the noise. We'll talk about what's genuinely working in AI cyber defense, where the real threats are coming from, and how to build a security posture that holds up — without starting from scratch. Should be a good one. Come join us. April 22 | 3:00 PM CEST Sign up https://lnkd.in/eppXJEqb #CyberSecurity #AISecurity #CISO -------------------------------------
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Alex Cunningham liked thisAlex Cunningham liked thisLots of laughs last night at A Night Out with GuidePoint Security at Grace by Nia 🎤🍸 A huge thank you to everyone who joined us for our first comedy night, and a big thanks to Kelly MacFarland and Artie Januario for keeping the room laughing all night long! Shoutout as well to our sponsors — Anvilogic, Astrix Security, Black Duck, Cyberhaven, Cyera, Living Security, Sublime Security, and Zafran Security — for helping make the night possible.
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Alex Cunningham reacted on thisAlex Cunningham reacted on thisA blood test changed how I see mental health. My doctor flagged my thyroid levels. Overactive. It was quietly fueling the anxiety and depression I'd been white-knuckling through — feelings I'd convinced myself were somehow my fault. They weren't. Mental health isn't a character flaw. It isn't weakness. It's biology. It's genetics. It's environment. It's trauma. It's a thyroid panel that comes back abnormal. It can happen to any of us — and it is happening to more of us than we admit out loud. May is Mental Health Awareness Month — recognized globally across dozens of countries as a dedicated moment to pause, reflect, and break the silence around mental health. One month where the world collectively agrees: this conversation matters. And while awareness is a start, what I really want to talk about is stigma. In 2026, too many people are still suffering in silence. Too many men still think therapy is for someone else. Too many of us confuse holding it together with being strong. Real strength? It looks like asking for help. It looks like telling someone you're not okay. It looks like going to the appointment, making the call, doing the hard thing. Vulnerability isn't weakness — it's the bravest thing I know. If you're carrying something right now, you don't have to carry it alone. Check on the people around you. Not the "hey how are you" check-in — the real one. The one where you actually wait for the answer. It's okay to not be okay. And it's more than okay to say so. #MentalHealthAwarenessMonth #MentalHealth #YouAreNotAlone #BreakTheStigma
Experience
Education
Licenses & Certifications
Honors & Awards
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BostonCISO Orbie Award Finalist - 2026
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CISOs Connect - Top 100 CISOs 2021, 2023
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Cyber Defense Magazine - Top Global CISO 2023, 2024, 2025
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Organizations
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Brandeis University Graduate Professional Studies
Advisory Board Member, Digital Innovation for FinTech
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CISO Executive Network
Member
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Cyber Risk Collaborative
Boston Leadership Board Member
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CyberEdBoard Community
Executive Member
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Degrees of Difference
Board Member
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Evanta CISO Community
Governance Board Member
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The CISO Society
Member
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Yogesh Deshpande
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For years, security teams worked to satisfy auditors and check compliance boxes. But today, the harshest critics of your cybersecurity posture aren’t regulators - they’re insurers. Because cyber risk has become an underwriting risk. If you can’t prove control maturity, you’ll pay more - or worse, find out your coverage means nothing when you need it. Cyber risk is now a pricing, eligibility, and survivability problem, a lot more than a technical issue. Real-World Lessons: When “Covered” Didn’t Mean Protected Even well-funded organizations are learning how unforgiving insurers have become: 1. Inchcape Australia v Chubb Insurance (2022) A ransomware attack caused business disruption, but the insurer ruled losses as “indirect” and not payable. 2. Hacked Business Loses Cyber Payout (Australia, 2023) A small business breach claim was denied - missing MFA and weak controls nullified the policy. 3. Supplier Breach, No Cover (2024) A company’s AU$30K response cost claim tied to a vendor incident was rejected - policy misalignment. These aren’t mere paperwork errors. They reflect a systemic shift: insurers now validate cyber maturity at the same depth attackers exploit it. Meeting the Baseline Isn’t Enough “Compliance-ready” doesn’t mean “insurable.” Policies are being restricted, repriced, or outright denied when: Controls exist only on paper, not in enforcement, and IR playbooks haven’t been tested in 12+ months. MFA or segmentation is missing on privileged or legacy systems, while Shadow IT, unmonitored vendors, or undisclosed prior incidents exist. You can’t produce evidence - metrics, logs, or test reports - on demand. Cyber insurance is no longer a safety net. It’s a maturity audit disguised as a policy. If you approach it like compliance, you’ll overpay or be left uncovered. If you treat it like risk management, you’ll earn leverage - lower premiums, higher trust, and resilience that outlasts any claim dispute.
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Identity and Access Management (IAM) is a key guardrail for secure access. This guide explains core IAM components, how they protect resources, and why they are foundational to Zero Trust security strategies. Read the breakdown: http://oal.lu/nq0Lr #IAM #ZeroTrust #Security
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Risk changes faster than your quarterly report. New misconfigurations, new exposures, new attack paths can appear in days, not months. Continuous Threat Exposure Management keeps your risk map current so you are fixing what matters now, not what mattered last quarter.
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"APIs also provide a larger attack surface than ever before. In many cases, APIs on the internet are just waiting for something to connect to them. When the incoming connection is from a known source, all is well; but unknown connections can be dangerous. Bad actors continuously scour the internet looking for open APIs, attempting to glean any information they can about the target. They then use this information to attack the API." https://lnkd.in/gQ7M7YiB
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