Rob Forman

The New Attack Vector CEOs Aren’t Watching: Calendar Invites Most CEOs in Central Texas know email is the biggest cyber threat in their business. But there’s a new attack vector slipping past security tools — and it’s hiding in plain sight. Your team’s calendar. Hackers have figured out they can use simple calendar invites to sneak in fake meeting links, impersonate trusted contacts, and get around security filters that normally block dangerous emails. These invites look normal. They land directly on your team’s calendars. And when the reminder pops up, people click. Here’s why this works so well: • Calendar invites don’t look suspicious • They often bypass traditional email filters • Outlook and Google sometimes add them automatically • Your team trusts anything that feels like a “work meeting” For a business, that means one thing: A single click can expose accounts, data, finances, or customer information. At CTTS, we’re helping Austin-area businesses stay ahead by tightening calendar settings, blocking risky invites before they hit the calendar, and removing suspicious events that slip through. Most business leaders never think about securing the calendar. But hackers do. If you want a second set of eyes on your Microsoft 365 or Google Workspace settings, schedule a free strategy session with CTTS. https://lnkd.in/gRnYBBbw #CTTSonline #AustinTX #RoundRockTX #GeorgetownTX #TaylorTX #Cybersecurity #ITSupport

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Confidence rarely collapses overnight. It erodes when IT becomes reactive instead of strategic. When oversight is episodic, reporting lacks direction, and recommendations stop before risk appears, control quietly shifts away from leadership. Here’s the question that matters: If your environment were evaluated objectively today, would it confirm your confidence or expose structural gaps? Click the link. Review it privately. You’ll know quickly whether your foundation holds under pressure. https://hubs.la/Q043GwVQ0 #CyberSecurity #ShieldHQ #Mindcore

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𝗪𝗵𝗮𝘁 𝗗𝗼𝗲𝘀 $𝟴𝟰𝟯,𝟭𝟱𝟬 𝗟𝗼𝗼𝗸 𝗟𝗶𝗸𝗲 𝗮𝘁 $𝟱.𝟱𝗠 𝗶𝗻 𝗥𝗲𝘃𝗲𝗻𝘂𝗲? What does a $843,150 growth strategy actually look like for a $5.5M MSP? This isn’t theory. It’s pulled directly from the Blueprint & Roadmap Report: 9% allocated to marketing 2% to business coaching 1.52% to sales training And five other strategic focus areas It’s all based on what top-performing MSPs are already doing to scale faster and increase valuation. Whether you’re at $50K or $10M+, this report shows how to spend smarter, not just more. 📰 Dive into the full report here: 👉 https://lnkd.in/enJKnFrC 💬 Drop a comment with “5-Blueprint Reports” at the top of your message to get the report free. Limited to the first 5. #MSP #MSPStrategy #GrowthBudget #Leadership #BlueprintReport #MSPEvaluator #ManagedServices

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The largest transfer of wealth in MSP history is happening right now. Most owners won’t participate. Not because they didn’t work hard. Not because they weren’t profitable. But because they weren’t ready. Revenue is easy to show. Readiness is harder to fake. Buyers are underwriting: – Retention, not just growth – Standardization, not heroics – Leadership depth, not owner dependency The quiet truth? Many MSPs will run out of time before they run out of effort. This window won’t stay open forever. And it won’t reward the loudest operators…only the most prepared.

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Many MSP owners blame the same villains for margin pressure. AI. Offshore teams. Automation. Market saturation. None of them are commoditizing you. Your positioning is. Most MSPs compete on what’s easy to compare: • “15-minute response time” • “99.9% uptime” • “2-hour average resolution” • “24/7/365 support” All measurable. All identical. All perfectly designed to turn you into a utility. When you compete on operational metrics, you train clients to shop you like electricity. Reliable? Yes. Strategic? No. The better you get operationally, the worse your positioning becomes: 💭 Fast response turns you into infrastructure 💭 Uptime guarantees frame you as maintenance, not insight 💭 24/7 support becomes a baseline expectation for your replacement Meanwhile: → A competitor with slower response times wins the premium contract → Your speed becomes their excuse to demand lower pricing → Your excellence becomes invisible because it’s expected You’re not differentiated. You’re optimized for comparison. THE MOMENT YOU COMMODITIZE YOURSELF Look at your last three proposals. What did you lead with? • Response SLAs • Uptime percentages • Support availability • Ticket metrics Be honest. Every time you lead with operational metrics, you tell the client exactly how to compare you. And price always wins that comparison. Operational positioning: “We guarantee 15-minute response time, 99.9% uptime, and 24/7 support.” Client translation: “Okay. So does everyone else. Who’s cheaper?” Strategic positioning: “We’ve helped three companies in your industry scale from 50 to 200 employees without technology becoming a growth constraint. Here’s how we’ll do the same for you.” Client translation: “Wait… they understand our business.” Same capabilities. Different game. One is replaceable. One is not. THE UNCOMFORTABLE TRUTH You’re not being commoditized by the market. You’re doing it yourself by competing where everyone else competes. • Everyone promises fast response • Everyone guarantees uptime • Everyone offers 24/7 support When you compete on the same metrics, you become the same option. And then you wonder why margins shrink. WHAT PREMIUM MSPs COMPETE ON INSTEAD Not metrics. Outcomes. 💰 Industry-specific expertise 💰 Business results delivered 💰 Strategic insight that saves money or enables growth Operational excellence still matters. It’s just the baseline, not the headline. When you position operations as the differentiator, you’re inviting price pressure. Operational competition creates: → Price-shopped renewals → Margin compression → “Necessary expense” positioning Strategic competition creates: → Automatic renewals → Pricing power → Irreplaceability You can’t build Revenue on Repeat by competing on response time. You can only build it by competing on insight. 👉🏽 So let me ask: What did you actually lead with in your last proposal? Operational metrics… or business outcomes?

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Hi Chief Marketing Officers, Executive Engagement is the only GTM motion where your own field teams can erode the very trust you’re investing in to build. For example, one of my clients is a $2.4B cybersecurity company. They built an Executive Sponsor Program to reach the CISO in their top 25 accounts. We brought in former Fortune 100 CISOs. We built peer-led CISO roundtables. And we positioned a 3–5 year CISO transformation narrative around risk. Those investments paid off in approximately 9 months. My client was now being included in conversations with CISOs and board-level leaders they’d never been able to reach before. But many of the account teams reverted to what they’d always been trained to do: - Feature/function comparison with their top 2 competitors - Turning it back into product demos instead of executive dialogue  - Feeling the quarterly pipeline pressure And we had some sticky conversations with CISO’s, who shared that the field’s behavior didn’t match the kind of executive conversation they wanted to have. So here’s the part most companies miss: The Executive Engagement engine works when it includes a compensation and enablement strategy. Right now, sellers are often paid for: ➡️ product revenue closed this quarter. But if you want them to build long term trusted relationships with CIOs and CISOs, they need to also be paid for: ➡️ expanding executive access in their accounts ➡️ influencing multi-year platform deals ➡️ and building relationships that drive renewal and expansion over time. Executive Engagement is a long-term revenue and relevance strategy at the C-suite level. Executive Engagement is having a transformation story a CISO will clear their calendar for so they can meet you, but also having the right commission structure that incents the behavior CISOs want to work with. That’s the real conversation, and the one very few are willing to talk about.

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96+ comments, hundreds of MSP leaders and advisors chiming in—credibility clearly hits a nerve. Here are 5 🔥 takes that stood out from the thread: Michael Maddox “...setting an arbitrary number that is not achievable is setting your people up to fail." Zack Bower: “Even in this perfect scenario your rep needs to make 125 calls per day, have 12.5 real conversations per day, and average 2.5 meetings per day over the course of 20 working days in a month. Do the math, not the hype drugs pedaled by influencers. " Josh Kotler "Yeah, that’s an insane KPI." Len DiCostanzo "My experience is 4-10 appointments for a solid, seasoned caller with a well developed playbook and a targeted audience with a real pain point." Will Ominsky " Sales needs both short-term (ready to buy) and long-term (future interest) focus. Unfortunately, many lean too heavily on immediate results, to the detriment of long-term success." Some patterns are starting to form. I’m curious—what’s your credibility edge when you walk into a room full of strangers? Link to the original thread in the first comment.

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Enterprises don’t buy tech.They buy certainty.Back in corporate compliance, we had rules that looked arbitrary—But they weren’t.✅ Must be doing $5M+ ARR✅ Must be at least 4 years oldWhy?Because these weren’t vanity thresholds.They were risk filters.$5M ARR meant:> “We have something to lose.”A startup with no revenue can sign any liability clauseBut there’s nothing to sue, no cushion to fall back on.ARR signals skin in the game and operational durability.4+ years old meant:> “We’ve made it through the fragile phase.”If you’re still alive after 4 years, you're statistically more likely to stay alive.Procurement teams know this.And when the average enterprise implementation takes 12–18 months,They need to know you will still be alive.Founders, here’s what that means for you:It’s not that your product isn’t good.It’s that your existence feels like a risk.You can promise the moon.But if you’re early-stage and pre-revenue -You are a massive risk.But here’s the shift we are seeing in AIYou don’t need $5M ARR or 4 years of history given the pace of AI progress and the inherent FOMO but you do need to build that credibility.Today, smart startups are signaling maturity early:✅ ISO 27001✅ SOC 2✅ ISO 42001✅ AI governance and privacy programs✅ Security audits and internal testingThese aren’t just compliance exercises.They’re market access tools.With GRC platforms and remote audits,Certifying a 10-person company is cost effective.This can be your moat.Not your algorithm.Not your UX.Your trust posture.Because when a buyer is choosing between 3 AI vendors with similar features?The one that has provable governance and accountability in place is the one that gets the green light.I'm interested to hear any old vendor requirements no longer being enforced.#AIgovernance #ISO42001 #Startups #EnterpriseReady

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Too many founders with compliance requirements still treat cybersecurity like a “big company problem.” You’ll hear things like: “We’re too small, people will understand.” “We don’t have the budget for that yet.” But if your business touches sensitive data—HIPAA, PCI, or anything else— you’re not just taking a risk. You’re violating an expectation. One that regulators, clients, and your future acquirer will not overlook. Cyber requirements aren't an IT line item. They are in fact a regulatory requirement. The cost of getting it wrong goes far beyond ransom payouts or downtime. You’re putting your team, your customers, and your valuation at risk. Boards need to push harder. Founders need to act sooner. Because if you’re waiting until something breaks— you’re not just behind. It is called willful neglect and it can result in much more than a slap on the wrist. #cybersecurity #founders #leadership #riskmanagement #compliance #startups #scaling

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Salesloft and Clari announced a merger. I call it a surrender. The legacy SaaS Unicorns are dying. Creative mergers and cap table restructuring is what happens when you burn through $937m in venture money and cannot grow sustainably. The VCs are paying for their mistakes. Employees equity will be crushed. Welcome to the new era of SaaS Wealth Destruction. But don’t worry, there’s a silver lining on the other side … BACKGROUND: When Salesloft acquired Drift in early 2024, I wrote: “To me, this is a merger that marks the beginning of many such mergers across all VC and PE portfolios that will play out in the next 1-2 years.” The Clari + Salesloft merger is another signal that the current winner take all investment and operating model no longer works. Over-capitalization no longer justifies premium pricing. The biggest and loudest conference booths no longer guarantee margins. The game has changed. Expect few years of “Creative Mergers” just to survive what’s coming.  Let’s first review the merged company: Drift + Salesloft + Clari + 9 other smaller acquisitions raised a total of $937M in venture funding and at its peak it had a combined valuation of $6.2 billion. Since the cap table was restructured with this merger; Clari’s real valuation is likely far lower - meaning investors and employees on both sides took a big hit. This is both a warning shot and a beginning of what’s coming. AI is going to accelerate such creative mergers and associated SaaS wealth destruction. Many Unicorns have to undergo this process to stay relevant or slowly fail. Ironically, the smartest Unicorn founders will choose valuation-crushing deals & rush to merge with other Unicorns. While such mergers destroy wealth and indicative of surrender, they are healthy for the overall ecosystem moving forward. Roughly 350 unicorns raised capital in the last 5 years. Many need restructuring. Why Salesloft + Clari merger make sense for the future? The real battleground of the future is CAC. CAC has already exploded in the past few years (60% for large SaaS). A platform like Salesloft + Clari has the potential  to subsidize CAC across multiple solutions and platforms while premium end point solutions will find it hard to survive and justify the ever rising CAC. Buyers are moving away from “Best of Breed” to “All in One” platform purchases. This also helps with the rising CAC. Every vertical will see the rise of multiple MEGA platforms - often a result of combining multiple Unicorns. With Clari + Salesloft’s combined product portfolio, data exhaust and high-quality customer base, Clari has a good shot at positioning itself as one of the MEGA revenue platform of the future. I hope more Unicorn founders have the courage to admit their mistakes and restructure before the music stops. But in the meantime, buckle up and get ready. We will see many more deals like this in the next 12-18 months. Welcome to the era of SaaS Wealth Destruction.

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“Feel like you're stuck in someone else's game?” Austin from CaaB.cloud – The MSP’s Cloud gets it. MSPs are frustrated with cloud providers that raise prices, limit flexibility, and bury them behind someone else's brand. CaaB - Cloud as a Business gives you back control. ✔️ Set your own pricing ✔️ Customize your cloud offerings ✔️ Deliver a fully white-labeled experience CaaB runs in the background. You stay in the spotlight. 🎥 Hear it straight from Austin in this short video: #MSP #CloudSolutions #WhiteLabelCloud #CaaBcloud #ChannelPartners #MSPMarketing #TechLeadership #CloudForMSPs Andy Abramson Mark A. Daley Bill (PhoneBill) McClain Jeff Pulver Charlene Ignacio Chief Problem Solver David Jooste The Managed Service Providers Association of America® Kevin L.

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Most SMBs would rate their MSP a “7 out of 10.” Not bad. Not great. Safe enough. But that “7” hides real costs you don’t see: 🔻 Downtime that drains revenue 🔻 Security gaps that create million-dollar risks 🔻 Unpredictable IT spend that kills control At Third Octet, we believe SMBs deserve better than “good enough.” Your IT should be a growth lever, not a hidden cost.

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🎙️ Fun data point from the editing room… We ran a quick word-frequency check across my interview episodes. The most-used word? 👉 MSP Not “AI.” Not “growth.” Not “security.” MSP. That’s not accidental. It shows up in conversations about: • Business models • Tooling decisions • Client outcomes • Automation • Risk • The future of IT services Because almost every strategic technology conversation eventually comes back to how MSPs actually operate. This clip pulls together a few moments where that word keeps surfacing — unintentionally, but tellingly. If you’re an MSP, vendor, or IT services leader, this is a reminder: You’re not adjacent to the conversation. You are the conversation. 🎧 Listen on Business of Tech: https://lnkd.in/eHX8hJP9 📺 Watch on YouTube: https://lnkd.in/g6dZ3ep 🇪🇸 ¿Habla español?: https://lnkd.in/e5ur76Wp (And yes… now I’m tempted to track the second most-used word.)

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The biggest mistake in choosing an IT partner: Buying a relationship. Instead of buying a system (process, reporting, escalation, documentation). Especially in regulated environments, “trust me” doesn’t pass due diligence. Comment CHECKLIST and I’ll DM the guide we use for evaluating providers.

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What gets labeled “insight” today is rarely raw and truthful. It’s aggregated, normalized, benchmarked, sanitized, and filtered through multiple incentives before it ever reaches a decision-maker. By the time it lands in marketing, product, or sales courts, it’s no longer a signal from a human. It’s an institutional artifact. Analyst reports, peer reviews, market surveys - these aren’t inherently wrong or useless. But they create distance from real buyers. And distance is where distortion compounds. I observe GTM teams making foundational decisions - positioning, roadmap bets, ICP focus, sales motion - based on interpretations of interpretations of buyer reality. The result is a strange, alternate reality of confidence: Confident decks Confident roadmaps Confident messaging All built on second- and third-hand understanding of humans. From the buyer side, the contrast is jarring. In direct conversations I have with CISOs and senior practitioners, the way vendors talk about “market validation” often doesn’t map to how buyers actually decide. Analyst influence is acknowledged, sometimes referenced, but rarely decisive. What is decisive? Context. Internal politics. Operational friction. Timing. Risk tolerance. Career exposure. None of that is successfully extracted to the deepest level from the analyst abstraction layer very well. This is THE structural flaw in the current GTM operating model: We’ve optimized for defensibility over accuracy. Analyst-backed decisions feel safer internally. They’re easier to justify upward. They reduce personal risk. But they don’t necessarily reduce market risk. I’m (and buyers are) far less interested in who validated your category than in: How often you speak directly to buyers Whether those conversations are ongoing or episodic Who inside your company actually hears the unfiltered truth And how quickly that truth changes decisions Let me be clear, I'm not anti-analyst. I'm anti-distance from the buyer. The teams that win won’t be the ones with the most reports or MQs. They’ll be the ones closest to the humans those reports attempt to represent. And right now, that gap is wider than most organizations are willing to admit. Book a call with me to accelerate revenue with CyberSynapse.io buyer intelligence: https://lnkd.in/gmpjZcZq

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It takes conviction to start an MSP. It takes humility to scale one. Most $10M+ MSP owners don’t want to hear this. But it’s the truth. The same drive that got you here is now holding you back. Early on, your conviction was everything. You believed you could deliver better service. You trusted your instincts over process. You ran through walls because no one else would. That conviction built your first few million in revenue. But here’s what happens at scale: Conviction without humility becomes the ceiling. You’re still the one making every critical decision. You’re still the one clients ask for by name. You’re still running through walls instead of building leaders. And your business can’t grow past what you can personally touch. I’ve worked with dozens of MSP owners through this exact transition. The ones who break through $10M all make the same shift. They stop being the hero. They start designing the system. They let go of controlling how things get done. They trust their leadership team with outcomes, not just tasks. Here’s the pattern I see: The MSP owner who scales learns to lead through people, not around them. So ask yourself this question: Where are you still running through walls instead of building leaders who can? Because the answer to that question is your growth constraint. Your conviction got you started. Your humility will get you scaled. Which one are you leading with today? If you’re ready to move from hero to architect, let’s talk about what that actually looks like in your business. Real scale requires real humility. 𝗣𝗦 If your leadership team can’t make decisions without you, you don’t have a leadership team. You have highly paid assistants.

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SOC 2 gets you in the room. It doesn’t make you enterprise-ready. Most Series A SaaS teams know that SOC 2 is table stakes for going upmarket. - It proves you take security seriously - It gets you through procurement - It keeps deals moving But let’s be honest about why it usually shows up on the priority list. Not because security is suddenly the right thing to invest in, but because enterprise revenue usually demands it. And that’s where a lot of teams mistake motion for maturity. - Clean reports - Controls “in place” - Audits passed On paper, everything looks solid. But in reality, the environment is still changing faster than the controls meant to govern it. - New tools - New vendors - New risk SOC 2 clears a hurdle. Maturity is what holds up under pressure. And maturity is what enterprise buyers actually care about.

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Legacy SaaS vendors are getting more desperate. It’s not just the tech, it’s the business model that’s at risk. Endless stories from customers about aggressive behaviors… Try and remove a legacy module? They will charge you the same price for your overall contract anyways. Want to use their “AI”? First pay for the SKUs to integrate their AI to their own legacy stack(s), which they cobbled together through acquisition and never integrated. Then pay for the AI SKUs. Then pay for some other SKUs that no one is sure even exist. Try and and bring in a modern age platform? Watch out! Your execs are bound to get a call from their CEO about the end of the world and compliance and blah blah blah. Customers are smart, and they see this happening. Ironically these behaviors are accelerating the timeline to move past legacy tech.

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Busy MSP Owners Don’t Scale but Structured Ones Do Being busy is not a growth signal (and it's tiring to hear TBH). It’s usually a warning sign. If your days sound like this: • “Got a couple mins?” • “Quick exception” • “Client emergency” • “Can you jump on this?” You’re not scaling a business. You’re building a job! Because you cannot: • Build a real pipeline • Close larger, cleaner deals • Raise prices confidently • 𝗦𝘁𝗲𝗽 𝗼𝘂𝘁 𝗼𝗳 𝗱𝗲𝗹𝗶𝘃𝗲𝗿𝘆 𝗮𝗻𝗱 𝘁𝗿𝘂𝘀𝘁 𝘆𝗼𝘂𝗿 𝘁𝗲𝗮𝗺 Inside a company that collapses the moment it gets busy. Operational maturity isn’t rigidity. It’s control. • Predictable delivery • Defined offers • Stable margins • Days/weeks that don’t implode January is brutal on MSPs who never fixed this. The cracks show early. If this feels like last year already,  that’s not failure, it’s a sign. 𝗡𝗲𝘅𝘁, 𝗜’𝗹𝗹 𝗯𝗿𝗲𝗮𝗸 𝗱𝗼𝘄𝗻 𝘁𝗵𝗲 𝗲𝘅𝗮𝗰𝘁 𝘀𝗵𝗶𝗳𝘁 𝘁𝗵𝗮𝘁 𝘀𝗲𝗽𝗮𝗿𝗮𝘁𝗲𝘀 𝗠𝗦𝗣𝘀 𝘁𝗿𝗲𝗮𝘁𝗲𝗱 𝗹𝗶𝗸𝗲 𝘃𝗲𝗻𝗱𝗼𝗿𝘀 𝗳𝗿𝗼𝗺 𝗠𝗦𝗣𝘀 𝘁𝗿𝗲𝗮𝘁𝗲𝗱 𝗹𝗶𝗸𝗲 𝗽𝗮𝗿𝘁𝗻𝗲𝗿𝘀. 𝗣.𝗦 𝘁𝗵𝗲𝗿𝗲 𝗮𝗿𝗲 𝘁𝘄𝗼 𝘄𝗲𝗲𝗸𝘀 𝗹𝗲𝗳𝘁 𝗶𝗻 𝗝𝗮𝗻𝘂𝗮𝗿𝘆, 𝘄𝗵𝗮𝘁 𝗻𝗲𝗲𝗱𝘀 𝘁𝗼 𝗯𝗲 𝘁𝗿𝘂𝗲 𝗳𝗼𝗿 𝘆𝗼𝘂 𝘁𝗼 𝘄𝗶𝗻 𝗝𝗮𝗻𝘂𝗮𝗿𝘆? If busy is the norm, DM me. I have a few ideas that can help!

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