HITT – Scaling Technology Conversations Through Organizational Growth – 8.25.26

Please join me in welcoming Graeme Scott. Graeme, thank you. So excited to have you back on the Tuesday call.

Yeah. Thanks, Cass. Excited to be here. And, as I was mentioning when people were jumping on here, was so great to see so many of you in Dallas last week for our partner summit. Was a hugely successful event, and, we’re glad that so many of you were able to join us. Now, we do have a last minute pivot here on the topic. So we had, lined up, and as Cass said, I was prepared to talk a lot about devices in the workplace.

And I will be using that topic for another date. But we had a cancellation of some folks that were gonna join me. Unfortunately, they couldn’t make. So I had to do a last minute pivot here, and I decided to go with a topic that I have a lot of conversations around with advisers.

I had several of those conversations last week at the summit, and so I wanted to kinda bring this to the audience, as a whole and just talk through what, you know, what is going on here. So, Chandler, if you wanna move to the next slide here, our title slide, today’s topic is called the ten fifty, one fifty, and one thousand. Now if you guys, played that in the Powerball this week, I’m sorry to inform you those were not the winning numbers. What those are is four numbers that I think every technology adviser should have somewhere in the back of their mind when they’re talking to a customer.

Because one of the things we know about business is that growth doesn’t happen smoothly. Companies simply get a little bigger every year and keep operating largely the same way. They can’t do that. Right?

They hit points where something that worked yesterday suddenly doesn’t work anymore. For example, the Wi Fi that was fine for eight people is no longer good for forty. The owner who knew every employee personally suddenly has people working for the company they don’t know or they’ve never met. The single Internet connection becomes three offices.

The handful of SaaS applications becomes forty. Ten cell phones become three hundred. And, eventually, you get to an organization with multiple offices, multiple clouds, multiple carriers, multiple business units, and sometimes nobody is entirely sure who owns what anymore. Those transitions are where opportunity lives for advisers.

So today, when I talk about ten, fifty, one fifty, and a thousand, we’re gonna look at what happens to the technology conversation as customers grow through those numbers. So let’s go to our next slide here, Chandler.

This is really the foundation for everything we’re gonna talk about here today. There’s a fascinating research at a Harvard Business School, which really kinda got this whole thing going, and it was recently published in the Harvard Business Review that looked at fast growing companies and what happens to decision making as those companies scale. And here’s what’s interesting. They don’t simply say cost customer companies get more complicated as they get bigger, which is generally how we tend to think. They identify actual organizational fault lines. So somewhere around fifty employees, founders begin losing the ability to maintain meaningful relationships with everyone in the organization. Around eighty, most companies begin needing more formal organizational structure.

And then we get to one fifty. So one fifty is what’s called Dunbar’s number. And Dunbar is Robin Dunbar’s research suggests that there’s a cognitive limit, roughly a hundred and fifty people, to the number of stable social relations a person can effectively maintain. And Harvard’s point is that as an organization approaches that kind of scale, you simply cannot run the business through personal relationships anymore.

So think about that. At ten people, I can walk across the office and ask someone what’s happening with x y z account. At thirty people, I probably still know who’s doing that. At fifty, that starts to get a lot harder.

At a hundred and fifty, well, now I need systems. I need processes. I need policies. I need management structures.

I need controls. And this is where I think it’s really it gets really interesting for us as advisers because what enables all those things?

Technology. Right? Identity management, device management, security policy, network architecture, cloud governance collaboration, customer experience, mobility data, all of these things that we talk about and sell on a regular basis are part of this conversation and enable this transition. So this isn’t, like, a sales framework that we just kinda made up on on on a whiteboard. There’s real organizational research underneath it, and that’s what we’re gonna talk about here today. So what we’re gonna do is take this research and ask, if the organization changes as it grows, shouldn’t the technology conversation change with it?

And so today’s thesis, if you will, is that the best advisers aren’t just having conversations that their customers need today. They’re already starting that conversation the customer is going to need next. And, obviously, we’re gonna take this from a network and mobility slant. That’s gonna be kind of primary our focus because, of course, that’s my bag. But I am gonna talk about security, CX, and cloud as well because those are all very important components of the of the technology stack. So, Chandler, next slide, if you will.

So this is the growth curve. I’ve basically broken the customer journey into roughly five stages. Okay? Start up, growth, established SMB, mid market, and enterprise.

And, again, I don’t want you to totally obsess about the numbers here. You know, should somebody with two hundred and forty seven employees belong in one box and someone with two hundred and fifty one in another? It’s not really the point. We wanna really kinda think of these as lanes, right, or warning lights.

The point is that complexity compounds as companies grow. More employees means more endpoints. More endpoints means more applications. More applications means more data.

More data, more locations means more connectivity. More connectivity means more dependencies, etcetera, etcetera. More dependencies, more technology means more things that can fail. And the financial stakes start changing too.

Right? Because there’s a final consequence to this complexity.

ITIC’s two thousand twenty five research found that ninety three percent of mid sized and large enterprises surveyed said that an hour of server downtime can cost three hundred thousand or more, and forty six percent put that number at above a million. So basically saying when technology fails, it’s a major problem for the organization. Now, obviously, that actual number is gonna vary dramatically based on the customer you’ve got. A hospital’s a lot different than a pizza shop.

A manufacturer’s a lot different than a law firm. But the point is that as customers move to the right of this slide, as they grow, technology failure or technology mismatch increasingly becomes a business problem. And as advisers, our job changes along with those phases and what we deliver. So let’s go ahead and break these, these stages out, jump into this growth curve here a little bit.

Next slide, if you will, please, Chandler. So let’s start with the start up. Okay? This is one to ten employees.

Right? Kind of, typically, you’ve got a founder who’s running IT as well as running sales, is running everything else. He’s running IT off a laptop and probably whatever router he got from the cable company or from five g. And he’s doing it between sales calls.

Right? He’s running sales. He’s running operations. They’re doing all these things. At five employees, that can actually work.

But that’s what makes this stage really dangerous because almost everything works until it doesn’t. Everybody knows the Wi Fi password. Everybody has access to Dropbox. The owner buys the phones.

Someone creates the Microsoft account. Passwords are being shared somewhere. And if somebody leaves, hey. Did anybody remember to turn off Bubba’s access?

But nobody knows. Right? This customer doesn’t need a digital transformation framework. What they need is good fundamentals.

Right? Reliable connectivity, good Wi Fi. You need to start talking about things like basic security, MFA, backup, perhaps a sensible cloud environment depending on the business, basic device oversight. You know?

Maybe mobile device management is too big for what they’re doing right now, but, you know, as they grow, these are the kind of conversations we have. Right? The opportunity for the adviser here isn’t complexity. It’s building a good foundation because the reality is this is the cheapest point in the customer’s journey to get things right.

Expenses or mistakes cost the least amount at this stage. Here’s the statistic that really kinda drives statistic, easy for me to say, that really kinda drives this home is Verizon, had a study in two thousand twenty five. Data breach investigations report found that ransomware was involved in eighty eight percent of SMB breaches compared with thirty nine percent of breaches at larger organizations. So what does that tell us?

That tells us that small doesn’t mean invisible. Quite often, it means underdefended. Right? And Verizon found something else interesting that, ransomware appeared in forty four percent of all breaches.

That’s up from thirty two percent last year. So planting basic network and security hygiene at this stage isn’t overengineering its good business. And your role as an adviser here is to assist as an implementer. Right?

Help them get those fundamentals right. But at this stage, you really wanna build these fundamentals with the expectation that the company may become twenty people, then fifty, then one hundred.

Because ripping everything out later is much harder to do than making one good decision at the beginning. And I know that’s challenging when every dollar counts at that startup level. Every dime you spend is a dime that comes out of your pocket, but it is important to at least have those conversations and lay the groundwork. So next phase, let’s take a look at this.

This is what I’m gonna call, Chandler, if you wanna swap the slide for me. We’re gonna call this the growth phase. So this is kind of where we’ve crossed ten employees. We’re in that sort of ten to fifty range.

And this is where things really do start getting interesting because what worked when everybody could sit around one table and have conversations starts getting harder. All of a sudden, new employees start showing up on Monday morning, and does anybody have a laptop for them? Did somebody create the email account? What applications do they need?

Who gives them access? And what happens to that access if they leave? Right? Maybe sales has put together a CRM.

Marketing just signed up for some cool new application that they need. Someone has a personal Dropbox account with customer information on it, and someone just put ChatGPT on their corporate credit card. Right? Welcome to growth.

This is what happens. Gartner has been tracking this decentralization of technology for years. In twenty twenty two, they said forty one percent of employees were already performing some form of technology work, and Gartner projected that by twenty twenty seven, seventy five percent of employees would acquire, modify, or create technology outside of IT’s visibility. And, of course, that’s even assuming you have an IT department.

Right? Maybe it’s just the founder who’s still doing that. So think about what that means for this customer. The technology estate isn’t being built exclusively by IT or the founder anymore.

Right? The employees are building it. That’s why somewhere between ten and fifty employees, you need to start talking about things like endpoint management, identity, SaaS governance, right, managed Wi Fi, security policies, CX tools, mobility. And I would absolutely start talking about mobile devices here.

Who owns them? Who pays for them? How are they provisioned? Right? What happens when somebody leaves?

Because twelve phones can be managed on a spreadsheet, but sixty phones become somebody’s job. Right? That’s a lot. And, again, this is where the adviser role changes because you’re not just helping them implement stuff anymore.

You’re becoming more of a guide. Right? You’re starting to say, hey. You’re fine today.

But if you’re planning to hire another twenty people this year, here’s what we’re gonna wanna have in place before you do that. That sentence is advisory. Right? And as they approach fifty employees, remember what starts happening organizationally.

The founder can’t see everything anymore. So technology starts replacing visibility with governance, and that is a key for growth. So now let’s take a look at the next phase. Chandler, if you wanna swap the slide there for me, this is what we call established SMB.

So now we’ve crossed that fifty level. Right? And this is really the sweet spot for a lot of advisers. A lot of you guys live, eat, and breathe here and love this area of growth.

Right? This is because this is where technology really starts becoming architecture. Maybe the customer opens a location or two. Maybe they acquire another company.

Half the workforce is all of a sudden remote. They’ve got employees in other states. Right? And suddenly, that single site network that was perfectly adequate isn’t adequate anymore.

We’re talking about things like redundancy. We’re talking about things like SD WAN. We’re talking about cellular failover. We’re talking about consistent security policy policies across locations.

We’re talking about unified endpoint management. We’re talking about cloud applications that those employees have accumulated over the last five or six years as they’ve grown. Right? We’re talking about a customer experience that may be completely different depending on which office a customer visits.

This is where I want advisers to stop stop looking at technologies individually. Right? We really gotta look at the aggregate. Don’t look at the circuit.

Look at the data journey. This is something that Chad and I have talked about a lot. Sam also talks about this in her presentations. Where are the users?

Where are the applications? Where is the data? How does it move between those locations? How critical is it?

What happens when that path fails? So that conversation has changed to that from when does your Comcast circuit expire. Right? That’s that’s a big shift in conversation.

And here’s another interesting dynamic. This is from a company called Capterra that’s a research firm. They found that fifty seven percent of SMB surveyed had experienced high impact shadow IT occurring outside the IT department’s visibility.

And although the term shadow IT sounds nefarious, it’s really just people trying to get their job done. Right? And it’s a natural consequence of growth. Again, as we talked about earlier, marketing’s now bought something.

Finance has bought something. Sales has bought something. Operations is connecting something. And, eventually, all those individual decisions by different departments becomes an architecture, whether it’s planned or not.

Right? And here’s another data point I like. This is from a company called Asana, and they did an anatomy of work, project. Knowledge workers reported spending roughly sixty percent of their time on work about work, essentially communicating, coordinating, searching for information, and dealing with processes around the actual work.

So that’s a great illustration of what this complexity can do to an organization.

The company has resources way more resources than it had at twenty employees, yet people are spending more time coordinating those resources. And remember our Harvard Harvard study we’ve cited at the beginning, we’re now moving toward that one fifty number, right, what they call Dunbar’s number. We’re approaching the point where personal relationships alone simply cannot hold an organization together. Formal systems aren’t optional anymore, which means that this is exactly where we as advisers have to move from individual products to architecture.

Don’t just look at the circuit. Again, look at that data journey. Where are the users? Where are the applications?

Where’s the data? How does it move? And that’s a very different conversation. So don’t wait for the second location to ask that.

The the key is to be proactive. Be that strategic partner. Don’t wait for the second location. Talk about SD WAN today before they need it.

Talk about cybersecurity today before they need it. Don’t wait for two hundred mobile devices to talk about MDM. Talk about it when they’re at fifty with plans for growth. That is the key.

Have that next conversation early and position yourself as a strategic adviser, a strategic asset for that company. So let’s move to the next one here, what we call mid market. Right? And this is when something interesting happens.

The customer all of a sudden has a lot of They have an IT department. They have IT people. They may even have a CIO. They’ve got security people potentially.

Right? They’ve got procurement. So some of you guys may think, okay. Well, they need me as an adviser less.

And the key truth is that they really just need you differently because their biggest problem isn’t necessarily a lack of resources anymore. It’s fragmentation. Right? We think about what happened during our last stage.

Marketing has its stack. Sales has its stack. Operations has its stack. Every office has another stack.

You know, maybe somewhere along the line, someone acquired a company, and they’re still running on a completely different network. You’ve got IoT devices that all of sudden jumped into the mix here. Nobody’s got them inventoried. You’ve got mobile devices spread across all sorts of different care carriers.

You’ve got SaaS everywhere. Right? All these applications. And increasingly, you’ve got AI tools now, of course, complicating everything.

Flexera did a two thousand twenty six state of the cloud survey and found that seventy three percent of opera organizations now operate hybrid cloud environments, and that creates complexity. Right? PwC research found that seventy five percent of its executives were concerned that unnecessary organizational complexity creates cyber and privacy risks. So, again, at this stage, these this fragmentation, all of this stuff that’s going on is creating risk, is creating challenges for the organization.

So your value as an adviser isn’t necessarily knowing Cisco better than their network engineer or Microsoft better than their cloud architect. It’s being able to see across the silos. Right? And I’m not gonna say anything, I’m not gonna say anything here that is, you know, revolutionary, but if you’ve got a five hundred employee customer and you’ve never had a cybersecurity conversation with them or you’ve never had a network security conversation with them, you’re late.

Right? If you’ve never talked about network resiliency, you’re late. If you haven’t talked about mobility, you’re late. Cloud governance, you’re late.

And increasingly, if you haven’t asked about AI, you’re late because someone is going to have those conversations. Right? You want it to be you. Your role here becomes somewhat of an orchestrator.

Right? You don’t have to personally solve all these problems for them anymore. You have to recognize the problem, help them recognize the problem, and figure out who are the best people to put in the room to solve it. And that is an incredibly valuable position for organization.

So let’s look at our last stage here, what we call enterprise. And enterprise, of course, you know, a lot of different people define this in different ways. For our purpose, we’re gonna define it as a thousand plus. This is the enterprise.

And at this point, usually, when you’re an enterprise, they’ve got resources everywhere. Right? They’ve got all kinds of resources. That’s not the problem.

The problem is getting all those resources moving in the same direction. Right? They’ve got multiple business units. Maybe they have multiple countries.

They’ve got multiple carriers. They’ve got multiple clouds, security platforms, mobility programs, maybe five different vendors solving essentially the same problem. Right? If we remember how we got here, all these different departments are building their own stacks, and now we’ve got an organization that’s got all kinds of things all over the place.

Enterprise IT is often less about adding another piece of technology and more about orchestrating complexity. And there’s a real cost of that complexity for these organizations. Right? McKinsey looked at decision making inside large organizations and estimated that ineffective decision making can consume more than five hundred and thirty thousand days of managers’ time every year at a typical Fortune five hundred company.

Now that is an unbelievably mind boggling number, and that, they calculate that at roughly two hundred and fifty million dollars in wasted labor costs. So you think about that. That’s a quarter of a billion dollars, not because the company doesn’t have enough people, because they have so many people, processes, systems, and decisions that coordinating everything becomes extraordinarily difficult. And that brings us right back to where we started.

Right?

Harvard’s research describes what happens when founder led relationship based decision making stops scaling. At the enterprise, we’re seeing the opposite end of that continuum. The organization now has plenty of structure. The organization has complexity within that structure.

That’s the problem. And that’s where a great adviser can can become incredibly valuable. You’re no longer saying, hey. I can save you eighty bucks on that circuit.

You’re saying, you’ve got two hundred locations, six carriers. You’ve acquired three companies and no consistent failover strategy. Let’s simplify that. Or your mobile contracts are spread across three regions.

Let’s rationalize them. Or you’ve got IoT deployments happening independently across five different business units. Let’s create some visibility. Or this is a real popular one right now.

Right? Your AI strategy is moving workloads into cloud and edge environments your network wasn’t designed around. Let’s take a look at that architecture.

So here, you become, you know, more of a navigator. Your value is knowing not knowing more about every technology than everybody inside that enterprise. You won’t. Your value again is being able to see across those silos and help them address that complexity within the organization.

So let’s move to our next slide here. We’re gonna zoom back out. Okay? Look at what happened to our role as an adviser.

Okay? At the startup stage, you were an implementer. Right? Let me help you get this right.

Let me help do this for you. Let me take some of this off your plate. I’m gonna take this on. Then we move to growth where we’re kind of more of a guide.

Right? Here’s what you’re gonna need next. As you grow your organization, these are the things you need to start thinking about as business owners. This is what’s happening.

At established SMB, now all of a sudden, we’re kind of more of a strategic partner. Right? Let’s make sure that technology supports where the business is going. At mid market, we’re coming in and we’re helping out as more of an orchestrator.

Right? There’s a lot of moving pieces here. Let’s help connect them. And then at the enterprise resources, you are a a sort of a navigator.

Right? You’ve got resources. Let me help you simplify this complexity. Right? Notice something here. As the customer got bigger, so did their IT department.

So did their resources. And the adviser’s role didn’t become less relevant, but the job changed slightly. Right? We moved from doing to guiding, to anticipating, to orchestrating, And I think that’s the real opportunity for us as TAs.

And, again, this is a conversation I have all the time with advisers. The best advisers aren’t just having the conversation their customer needs today. They’re already starting the conversation their customer is going to need next. So let’s slide here as we wrap this up.

What do you do tomorrow morning? What do you do with this information? Right? I want you to do something really simple.

Pick five or ten of your customers. Right? Don’t pick your biggest. Pick customers you know reasonably well and put them somewhere on this curve.

Then ask three questions. First, where are they really in this curve? Not just employee count, but, like, operationally. Okay?

Are they still behaving like a twenty person company even though they’ve got well over a hundred employees? There’s opportunity there. Right? Second, start thinking about what starts breaking next for these customers.

Right? Where are you gonna start to see cracks? Is it in connectivity? Is it in security?

Is it in mobility? Is it in cloud, CX, IoT? Whatever it is, have start trying to identify where those opportunities may start to emerge within your customer base. And then this is the most important question.

What conversation am I not having yet that I should be? Because if you can identify the problem six months before your customer identifies it themselves or better yet starts feeling the pain of it, you are no longer the person they call when they need a quote. You’re the person they call when they’re trying to figure out what to do, and that is where, ideally, we want to be. So remember those numbers.

Right? Ten, fifty, one fifty, one thousand. At ten, informality starts getting harder. Fifty, founder visibility starts breaking down.

One fifty, that Dunbar number. Right? Relationships alone can no longer run the organization.

And then at a thousand, complexity and fragmentation become the problem. So don’t wait for your customers to cross that line. Start the conversation before they get there. Alright.

So there you go. That is my what’s my book name? That is my, hit there. Why don’t we go ahead and see if we can open that up to any questions?

Did we have any in the chat here? Let’s go to q and a. Cass, you wanna come back in?

Yep. I’m here.

I’m waiting right now to see if we’ve got any questions that’ve kinda come in. We do have quite a bit of conversation that’s been in here today.

That’s good. Yeah. So, again, yeah, major issue. I think, Eric, you raised a good point.

Right? Shadow IT is and, again, you know, shadow IT is such a nefarious sounding term. Right? It’s like we’ve got this shadow organization.

It’s really just employees trying to do their job, and I think we wanna just give them the structure to do that within the organizational confines. I mean, even an organization like Telarus, you know, we have these conversations all the time about shadow IT. How do we you know, these tools that we know are out there that are popular, how do we implement them into what we’re doing in our daily business? So alright.

And I also see a lot of folks in the in the call are asking about this deck. The actual recording of this, if you wanna screenshot anything that you might have missed, is gonna be available on Telarus University. It’s under the forums tab. I will share a link to that momentarily. But that way, you guys can go back, screenshot what parts you want, and then that way, you’ll be able to see that information and be able to kind of create whatever you need in order to get that to your customers as well.

Yeah. A question here from James. What’s the difference between Shadow IT and Shadow AI? I mean, I think, obviously, AI is is kind of a an extension of Shadow IT.

Right? And Shadow IT is essentially going out there, getting applications, doing things within the organization that are not sort of approved in a general organizational sense. ShadowAI would be implementing AI solutions as part of that. Right?

Bringing in like, putting company data into things like ChatGPT or or Claude. Right? These are major problems that organizations are are coming to. So, you know, AI is driving a lot of this conversation, right, especially as organizations start to get bigger because we know that their employees are using these tools.

Right? They are so readily used. The question is, what information are they putting into these tools that is proprietary data, that is organizational data? Right?

That’s what organizations and companies don’t always know, and that is one of the big concerns.