Addressing Security Concerns in B2B User Experience

🔍 Anatomy of an Modern B2B Business Email Compromise (BEC) Attack A recent Trend Micro™ Managed XDR investigation uncovered a sophisticated B2B Business Email Compromise (BEC) attack, where a threat actor manipulated an ongoing email conversation between three business partners over several days. By compromising an email server and strategically replacing recipients, the attacker successfully redirected funds to their account—all while the victims believed they were communicating with their trusted partners. 🚨 Timeline of the Attack: 📅 Day 1: • T+0:00 – Partner A sends an invoice reminder to Partner B, copying Partner C. • T+4:30 – Threat actor intercepts and sends an email with fraudulent banking details from a compromised third-party email server. • T+11:00 – The attacker resends the email, this time using a compromised Partner C account to reinforce legitimacy. 📅 Days 2-5: • T+15:00 – Partner B, unaware of the compromise, acknowledges the invoice and requests additional details—unknowingly communicating with the attacker instead of the real Partner A. • T+5.02 days – Partner A (still unaware) provides business details, but the email is received by the attacker, not Partner B. • T+5.17 days – Attacker confirms details and reissues fraudulent banking instructions. • T+5.64 days – Partner B deposits the funds into the attacker’s account. • T+5.66 days – Partner B informs ‘Partner A’ (the attacker) that the transfer is complete. By the time Partner A and Partner B realized the fraud (12+ days later), the funds had already been moved. 🔑 Key Insights from the Incident: ✔️ Sophisticated Manipulation: The attacker gradually replaced real recipients in email threads, ensuring the conversation seemed normal. ✔️ Social Engineering & Trust Exploitation: By mimicking writing styles and leveraging auto-complete features, they maintained credibility. ✔️ Weak Email Security Enabled the Attack: A misconfigured third-party email server allowed fraudulent emails to bypass security checks. ✔️ Strategic Patience: The attacker waited 4.5 hours before injecting fraudulent banking details, ensuring it appeared as a legitimate correction. 🛡️ How to Defend Against BEC Attacks: ✅ Strengthen Email Authentication – Implement DMARC, SPF, and DKIM to verify sender legitimacy. ✅ Enable Multi-Factor Authentication (MFA) – Prevent unauthorized access to email accounts. ✅ Monitor for Anomalous Activity – Look for suspicious email forwarding rules and unauthorized logins. ✅ Educate High-Risk Employees – Train finance teams to verify banking details via secure channels before transferring funds. ✅ Establish Out-of-Band Validation – Require phone/video call confirmation for financial transactions to verify sender identity. 💡 BEC attacks are getting more sophisticated, but proactive security measures can significantly reduce the risk. 🔬 Full Research in Comments Section #DeepDive #CyberSecurity #BEC #ThreatIntelligence #EmailSecurity #TrendMicro #SOC

I've been writing about go-to-market for years. But cybersecurity is different. Not because the product is more complex. Because the customer doesn't know how to evaluate you. Think about it: When someone buys project management software, they know what good looks like. They've used Asana, Monday, Jira. When someone buys cybersecurity, they're buying protection against threats they don't understand. They don't know: Which attack vectors matter most for their industry How to test if your solution actually works Whether your detection rate claims are real or marketing What "good" threat intelligence even looks like This is the expertise gap. And it creates a trust problem. Time to Trust is longer in cyber than in any other B2B category. Your job isn't just to sell. You need to close the knowledge gap first. Here's how: 1. Educate without overwhelming Don't lead with technical jargon. Lead with business impact. "Ransomware can shut down your production line for 48 hours. That's €2.3M in lost revenue. Here's how we reduce that to 6 hours." Not: "Our AI-powered EDR uses behavioral analytics and machine learning to detect zero-day exploits." 2. Show credibility through context A demo is worth 100 slides. But not a generic demo. A demo using their environment, their data, their workflow. Make it real. Make it theirs. 3. Make validation simple Your customers aren't security experts. They can't run penetration tests or evaluate detection rates. Give them clear, hands-on ways to see your product work. Onboarding should be smooth. Their first hour should make sense. If they need a PhD to understand your dashboard, you've lost. The mistake most founders make: They assume trust comes from technical superiority. It doesn't. Trust comes from transparency, education, and making the complex feel manageable. At CyGO Entrepreneurs, we don't pitch features. We build trust by co-creating with Design Partners who validate our approach before we ever talk to a prospect. By the time we show up for a sales conversation, we're not explaining how the product works. We're showing proof it already works for people like them. That's how you shorten Time to Trust. What's your experience building trust in cybersecurity sales? How do you close the expertise gap with customers who don't know how to evaluate you? P.S. I wrote a full breakdown of this in my latest newsletter. Link in comments if you want the deep dive. #CybersecurityGTM #SalesStrategy #TrustBuilding

The Federal Trade Commission recently announced a #datasecurity and #marketing consent decree with a B2B security company. Here's 4 areas to focus on for your org's security, marketing, and vendor management ⬇️ The FTC alleged the company had inadequate security practices to protect business customer data, and did email marketing that violated CAN-SPAM. It also alleged the company made false claims about security practices and compliance with HIPAA and Privacy Shield. The complaint details how it suffered multiple threat actor intrusions into its network resulting in the threat actor accessing live video feeds on its business customer sites, and exfiltrating gigabytes of customer data, including site foorplans, camera image and audio recordings, employee details, and wi-fi credentials. It also claims the threat actor was able to do #facialrecognition searches, potentially on people at customer offices and sites. The company agreed to pay a $2.95M penalty, and to 20 years of remedial obligations for its data security and marketing practices.    To help protect your organization, focus on these areas:   1️⃣ Security Program. Confirm your organization's security program uses the types of security controls at issue in this case: 🔹access management controls (unique & complex passwords, role-based access controls, & MFA); 🔹data loss protection; 🔹logging and alerting; 🔹vulnerability management protocols (product security testing, risk assessments, vulnerability scans, and pen testing); 🔹network security controls (disabling unused ports/protocols; properly configuring firewalls); 🔹encrypting customer data in transit and at rest; and 🔹appropriate information security policies and procedures that are followed and trained on enterprise-wide. 2️⃣ Email Marketing. Have working email unsubscribe functionality and required CAN-SPAM disclosures even in B2B emails. 3️⃣ Vendor Selection and Contracting. Confirm vendor selection and contracting process would catch vendors like this one and require appropriate security obligations, breach reporting, and accountability for damages. 🔹Consider whether spend amounts or assumptions the vendor wouldn't deal with customer data would skip these reviews or contract provisions. 🔹The action didn't focus on whether business customers were told their video cameras were accessed and sensitive corporate data was stolen; validate your organization's vendor contracts would require this. 4️⃣ Vendor Assurance. Would your organization's vendor risk management approach have verified this vendor actually had the security practices it touted? Consider whether criteria for validating vendor commitments need to be adjusted--such as to require and review independent audit results, or to conduct your organization's own assessment or audit. 🔹If the allegations are credible, it sounds like the vendor made false security commitments that weren't implemented, so its contractual commitments may have been illusory.

If everyone's a super-admin in your HubSpot, you're one disgruntled employee away from disaster. 𝘛𝘩𝘦 𝘙𝘪𝘱𝘱𝘭𝘪𝘯𝘨/𝘋𝘦𝘦𝘭 𝘭𝘢𝘸𝘴𝘶𝘪𝘵 𝘪𝘴 𝘮𝘢𝘬𝘪𝘯𝘨 𝘸𝘢𝘷𝘦𝘴: 𝘢𝘯 𝘢𝘭𝘭𝘦𝘨𝘦𝘥 𝘪𝘯𝘴𝘪𝘥𝘦𝘳 𝘵𝘩𝘳𝘦𝘢𝘵 𝘸𝘩𝘦𝘳𝘦 𝘢𝘯 𝘦𝘮𝘱𝘭𝘰𝘺𝘦𝘦 𝘴𝘦𝘢𝘳𝘤𝘩𝘦𝘥 𝘧𝘰𝘳 𝘢 𝘤𝘰𝘮𝘱𝘦𝘵𝘪𝘵𝘰𝘳'𝘴 𝘯𝘢𝘮𝘦 23 𝘵𝘪𝘮𝘦𝘴 𝘗𝘌𝘙 𝘋𝘈𝘠 𝘪𝘯 𝘙𝘪𝘱𝘱𝘭𝘪𝘯𝘨'𝘴 𝘊𝘙𝘔 𝘵𝘰 𝘴𝘱𝘺 𝘰𝘯 𝘤𝘶𝘴𝘵𝘰𝘮𝘦𝘳𝘴 𝘤𝘰𝘯𝘴𝘪𝘥𝘦𝘳𝘪𝘯𝘨 𝘴𝘸𝘪𝘵𝘤𝘩𝘪𝘯𝘨 𝘱𝘭𝘢𝘵𝘧𝘰𝘳𝘮𝘴. This isn't just B2B drama (okay, a little) - more than that, it's a wake-up call to start treating your CRM like the revenue-generating asset it is. Think about what's in your HubSpot instance right now: • Every sales opportunity and its value • Competitive intel from prospect conversations • Customer churn risk indicators • Strategic account expansion plans • Internal notes about pricing negotiations Yet I see the same security mistakes with nearly every client I onboard: • Everyone has admin access, "just in case." • No audit trails enabled for sensitive data • Zero user permission reviews • Deal data visible to the entire company • Former employee accounts are still active months/years later The truth is that your CRM security isn't just about external hackers. It's also about appropriate internal access controls. If someone wanted competitive intelligence on your business, your CRM is literally the first place they'd look. But with proper HubSpot governance, you can prevent these issues without sacrificing usability. Three immediate steps to take: • Check out the HubSpot's Security Health Checkup (yes, it exists) • Implement proper role-based permissions • Establish a quarterly access review process • Configure audit logging to track who's viewing what It will be hard to catch an insider threat, but there's no reason your CRM should be so exposed. #CRMSecurity #HubSpot #DataGovernance #RevOps

As 2024 wraps up, I wanted to share something special with my fellow technical co-founders and leaders - a collection of hard-earned insights from our engineering team's journey building authentication platform for B2B SaaS applications. We've just released three detailed technical guides I wish we had when we started: 1. The SAML Security Handbook This isn't the standard overview you find elsewhere. We're talking about real attack vectors we've encountered and the exact patterns that passed stringent enterprise security audits. 2. B2B Authentication Architecture Guide Early architectural decisions can save months of refactoring. We break down the Universal vs Organization-based authentication nuances with actual scaling considerations. 3. Advanced SAML Implementation Playbook Most implementations break at the edge cases. We've documented surprising scenarios we encountered while scaling to enterprise needs. Consider this our end-of-year gift to the B2B auth tech community. These guides go deep into the complexities that emerge with enterprise needs - the kind of challenges that aren't covered in standard documentation. I’ve pinned them onto my profile so that you can access them anytime! Feel free to DM me for any questions. Here's to building more secure, scalable systems in 2025! 🚀 #EngineeringLeadership #CIAM #SecurityArchitecture #TechCTO

Security teams in B2B SaaS - here are the top 10 AI risks slowing deals, hurting customer trust, and causing costly fines: 1. Ungoverned use Some security teams accidentally (or even intentionally) create "gray areas" about which AI tools are okay for use. Others ban it entirely (or so they think), encouraging people to use personal ChatGPT accounts. This create shadow AI. 2. Accountability by committee Enterprises love their committees. And they can ensure the right people are involved in decision-making. But that doesn't mean everyone should get a veto. Without the right structure, it's be tough for employees to know what they should be doing with AI. 3. Stalled deals CISOs are focused on AI-related risks. So are legal teams - some are even trying to ban AI use outright in contracts. If you don't have a solid story about how you protect data while using AI, expect pushback. This means slower revenue and angry business leaders. 4. Vendor AI feature creep On the other side, your vendors are adding AI into every aspect of their products. This has benefits, but they are probably facing the same problems you are in terms of protecting data! Staying on top of every new AI-powered feature is tough. 5. Lack of architectural understanding Think you have an "internal" AI application? -> Where is the model deployed? -> What is the data retention policy? -> Can third parties review your data? Many security leaders I ask this question of can't give confident answers. Not knowing these details is a risk itself. 6. Inconsistent data handling Do you just slap "CONFIDENTIAL AND PROPRIETARY" on everything? 50% of company web sites I look at have something labeled this way that can be found by a  Google search. If you don't know what is actually sensitive and what isn't, how are you going to protect it from unintended AI training? 7. No standard operating procedures -> Every day a new adventure? -> No solid incident response plan that considers AI? -> Jumping hoops because marketing wants a new tool? If this sounds familiar, it's because you don't have solid procedures to measure and manage AI risk. So you are re-inventing the wheel every time. 8. Auditor scrutiny SOC 2 is table stakes for most companies selling B2B. And unless you have an auditor who just checks the box, they are problem asking some hard questions about how you use AI. Do you have solid answers? 9. Customer-facing bots with no guardrails Having a Large Language Model (LLM)-powered chatbot is common these days. But if you just let customers loose on it, the results can be...embarrassing. Product teams deploy quickly. That makes it tough for security teams to put the right controls in place. 10. Regulatory pressure A whole alphabet soup of governments (& agencies) like the: -> EU -> SEC -> FTC have strong opinions about AI. And are already slapping companies with fines. Understand red flags for regulators (and how to avoid them). Which of these hit home?