“vCIO Talks” w/ Bryan Lukralle

In this episode of “vCIO Talks”, Simon chats with Bryan Lukralle, VP Client Strategy at Charter Technology Solutions (CTS).

Charter Technology Solutions is an MSP primarily servicing Charter Schools in New York state.

vCIO Talks is a podcast about vCIOs talking to vCIOs, discussing their business and their vision for the MSP and strategic services industry at large.


[Simon] Hi, welcome everyone to vCIO Talks. I am Simon, Co-Founder of Propel Your MSP, and I have the pleasure of being joined by Bryan Lukralle, who is VP of Client Strategy at CTS – Charter Technology Solutions. Thanks for doing this today, Bryan.


[Bryan] No problem, Simon. I’m happy to do it.


[Simon] Really appreciate it. Okay, maybe we dive into it. So, how about you give us a bit of your background and how you got into the MSP space?


[Bryan] Sure. I have been in the MSP space since 2009. Straight out of college. I’d like to say the MSP space chose me. I didn’t choose it. I came out of school with a math or history degree. I was going to be a teacher and the economy was a little bit interesting coming into 2009, So I happened to land at an MSP in New York because my dad was a customer of theirs. They sent their leadership into their office because they were having Citrix issues and my dad was one of the louder people about the issues that were going on and, in the midst of complaining about an issue, asked the guy that had come there (who was their director of operations), “Hey, are you guys hiring? My son’s looking for a job and he’s good with computers.”

So, 14 years later, I am still in the space. I’ve had opportunities to leave and go work internal and I always come back to the idea that I like the idea of doing good work for clients, making clients happy, and not getting bored with one single environment.

I love the challenge of different personalities, different types of technology, different environments. I find it very interesting, so that’s kept me in it for all this time. I’ve worked at 3 different MSPs in those 14 years. I worked at a 70 person one that was New York City focused. My last one was larger – I think when I left, it was 400-ish people. The company I’m at now, CTS, we’re focused on the education and not-for-profit verticals. We have a large portion of the charter schools in the New York City metro area. We’re about 80 employees.

I’m running our client strategy team, which makes up two main departments. It’s client management (the people that manage clients), vCIO type people, and our Solutions architecture team that designs all of the technical Solutions for clients.


[Simon] I guess it makes sense that you ended up in an MSP for school vertical after wanting to be a school teacher in this case.


[Bryan] For sure. When I left my last place, we were private equity backed, fast growth, and the pace was very hard to sustain. So, when I left, I was looking to do something smaller, but also try to get into more of a specific vertical. My mom is a teacher, my aunt is a teacher, and I have a 4-year-old now. One of his most favorite things is talking about school. So, naturally, doing something with schools was what I was hoping to do, and I got a really good opportunity. It’s been really awesome. I’ve been there for about four months now.


[Simon] You are VP of Client Services. You were saying that you manage the group. Why don’t you talk a little more in detail about the people who report to you and what you’re responsible for?


[Bryan] The challenge in our industry is that there’s a lot of different titles for what people do and even names of departments. We are technically “client-“ I’m VP of “client strategy,” but “client strategy” and “Client Services,” I’ve seen both used synonymously. The way that we are structured, we have a Deputy Director, effectively a director in charge of each of those two departments that report to me. One that’s client management, one that’s Solutions.

In our client management team, we’re structured a little differently than what I had put in place at my last place and what I experienced at my first MSP where we had a tiered structure. A vCIO top level, very technical person, and then an account manager type person underneath. The way that we’re structured at CTS is basically a single resource who we call a “client manager.”

That client manager is responsible for much less clients than the way that things were structured at my previous MSP, where we would have maybe 30-40 clients. Our average client load is 8 to 10, so the benefit there is they’re able to spend a lot more time with their clients. They get to know them a lot more. They know their environments very well, and frankly, it makes the whole process of communicating new initiatives a lot easier; because a single client manager could spend a half day and talk to all their clients. Versus sending out an email via MailChimp and hoping like hell that someone responds back.

It’s made the process of new product innovation a lot easier. We’ve done a lot of that since I’ve been there. We’ve been rolling out new technologies, and leveraging Propel, which I can refer to later, has helped a lot with that as well.

In general, I have two direct reports. We have, I believe, seven Client Managers across our, 60-ish, full MSP clients. Then we have, in our Solutions team, about three people reporting to our Deputy Director.


[Simon] What’s the profile of your Client Managers? In that case, if they’re doing everything for your clients?


[Bryan] We have a very mixed group. We have, of that group of seven, about half and half: people who are more technical background and people who are more school background. We’ve had some Client Managers who are ex-directors of operations at charter schools and schools in general, who really know the school space and how to interact with clients in the space; but were less technical when they joined. They’ve obviously absorbed a lot since then.

Then there are some people who come from the technology services space, whether it be an MSP/Telephony ISP-type place where they didn’t know schools as well, and they’ve learned the school space. We have a good mix, but we do have some people that are more technical, some that are less technical. We have senior Client Managers versus Client Managers, which really comes from experience being here. We lean heavily on the Solutions team to help with some of the heavier technical work. So, designing out a new school build is not really done by the client manager. It’s done by the Solutions people as a partnership.

So, client manager comes with the client specific information. The Solutions person comes with the technical know how knowing our product catalog and they combine to develop a finished solution.


[Simon] So will they often meet the client together or how does that work?


[Bryan] They’ll meet together. A lot of our work we do is actually new builds. A lot of our charter schools started with us. So, coming through different streams of new clients, we’ve had some clients that started with a single school and have grown into a network where they have 2, 3, 4, 5, 6 schools. We are involved with everything from the low voltage cabling to design of MDFs, IDFs. We do pretty much everything and our project management is really structured to run it almost like a GC from start to finish. There is a lot of that partnership between the Client Managers and the Solutions people when it comes to new builds.

The other thing that’s unique about our space is that, because we are working with a lot of schools that get E-Rate funding from the federal government, there’s a very specific cycle that we go through where we are designing a lot of this work at the end of the year, going into the spring. Quotes are all getting signed around the same time; and then our summers tend to be a lot heavier than an average MSP because a lot of work has to be done in the Fall, because some schools can’t be left open at night for someone to be there to do a firewall cut over. It has to be during the day, and you obviously can’t turn off the firewall in the middle of the day when kids are in school.

So, we have to truncate a lot of our project schedules into the Fall. It’s unique. So, it’s new to me, but these guys have been doing it. CTS has been in business for 13 years, so they’ve been doing it for a while, but the company has grown significantly since the pandemic. The company was probably less than 30 people before 2020 and we’ve doubled and a half in size since then.


[Simon] You were talking a little bit about the budget cycle, in that sense that you’re getting quotes out and then doing the work in the Fall. Speak to us about your strategic services, what they look like, and how you deliver.


[Bryan] Prior to me joining, we’ve had an established cycle. Our clients have a very specific asset life cycle that we track in our- first, we enforce via our MSA, but then we track via our existing tools, which include ConnectWise and IT Glue. We track purchase, expiration date, age that things need to be replaced and even the average cost of replacements so clients, in theory, know.

I’d say prior to me joining, a lot of it was done with spreadsheets and a lot of manual work and we weren’t really able to provide more future casting on that stuff. It was very much when we would come into the spring and we have to plan out all of our E-rate funded infrastructure upgrades, we would look at what’s old, put it into a quote, figure out the labor, and tell the client, “This is the stuff that has to get replaced this year.”

We already had that cycle set up, but we were missing a lot of the more detailed analysis, more detailed reporting, making it a little bit easier for the clients to understand and to start to get more commitments up front, so we can better plan over the course of the year.

What we do is a quarterly (OTR) organizational technology review, but effectively, we only do them three times a year because in the Fall, no one wants to meet about anything because the Fall is a time to get stuff done.

So typically, April is the last one, October is the first one, and then there’s one that is sprinkled in around January. The plan is effectively: in the Fall, we are doing a larger assessment of everything that clients need to be doing, setting the stage. Getting feedback from them on what they would like to do and also looking at what was completed over the Fall, make sure everyone’s comfortable. Based on those conversations, we have our directive on what to move forward on. So, when we come in in January, February, we have more finalized numbers. For example, “Here is what you want to accomplish from the perspective of asset replacement. Here are the things that you want to do that are outside of that. New security investments for cyber security, maybe migrating to the cloud because you don’t like the way your setup is today. Maybe you want to put in print management because you print a lot in schools.”

The goal is to do an audit and review all assets in the Fall, get agreement or general agreement. In the Spring, or let’s say late Winter, get more firm agreement on numbers. Then that last meeting in April/May is more of a maintenance visit to make sure that everyone’s comfortable with what’s going to happen in the Fall. Then Fall, we plow through the Fall, projects get done, and then we start again in the Fall.


[Simon] Makes a lot of sense. Who does those different tasks and who are you meeting on the client side starting in the Fall?


[Bryan] In terms of doing the actual technical audit, that is a kind of shared responsibility between the Client Managers and the Solutions people, because there are some questions on those audits that are more technical than they’d be able to figure out from just digging into their documentation.

I will admit, in this conversation, that this is going to be our first time going through it with the new structure that I put in place. This is based on what I’ve done in the past and what’s worked really well. We are still working through all of the mechanics, but the plan is that it’s going to be a bit of a shared effort between Client Managers and Solutions where we’ll design – audit how clients are set up today.

The Client Managers are fully capable of driving through the asset side: looking at age of equipment, knowing their clients well. The part that they’re going to need a little help with is, the audits that we’ve designed are very heavy on cybersecurity. Part of the work that’s going to be happening in August and September is auditing all of our clients against the cybersecurity standards that we want to apply based on not-for-profits and K-12.

I’m going to be probably pretty hands on with it because I helped design a lot of the cybersecurity stuff that we’re doing this Fall. I’d say it’s a shared effort that is still driven by the client manager. They are responsible for it and then they are leveraging Solutions and myself as a resource to help them get the information they need into the system.


[Simon] So you start with the audit, then you meet the client? Or do you start by meeting the client and then you audit?


[Bryan] Great question. In order to do the audit, there is information we need from the client. So, we start the process by having the conversation with the client that, “We’re going through this process. We need some information from you.”

We’ve streamlined what we need to actually gather via a quick questionnaire, so we’re not having too much back and forth. We want to just get a lot of simple stuff on the cybersecurity side: “Do you have cyber insurance? How much do you actually have? Do you have policies and standards? Have you ever done a risk assessment before?” Stuff that we have to get from them from their lips; But most of the other stuff we can look at their environment and go, you know, they’re not doing security awareness training. They don’t have dark web monitoring. They’re not doing this and that. Then be able to answer the audit appropriately and go, okay, here are all the gaps that we found. What are the things that we want to attack in year one to get them to a, if they’re at a 50 now, how do we get them to a 65 and then hopefully get them to an 85 or 90 the following year?

Again, schools have limited budgets in general. Charter schools have even more limited budgets. There is an expectation that it can take more than one cycle to get a new improvement into a school because they have to push through with the limited amount of funds to pay for the space they have, the teachers, all the materials. There’s a lot that they have to pay for. Technology is not often the first thing on their mind. That has changed a bit because of the pandemic, because again, most of our schools have heavy Chromebook populations that are out there with their students that tend to break a lot. There is a lot of cost there that it’s just part of instruction now and there’s not a lot of ways around it.

Even the schools that don’t want to leverage technology are forced to via some of the state testing that they have to do that has to be done on actual devices. You can’t use scantrons anymore.


[Simon] So you have a pre-audit discussion with the client, then you audit, and then then that’s when you come in and do more of a needs analysis, see if anything’s changed on their side, where they want to go? Or how would you frame that?


[Bryan] The idea is that we have to do some pre analysis. There’s some initial questions, like letting them know that we’re doing this. We let everyone know in May that we were going to be doing a cybersecurity assessment in the Fall, and that we would probably need to get some information from them to complete it.

The idea is that that initial conversation in October is not going to be what I would consider a completed assessment. We’re going to come in with what we think they need to do based on what we’ve seen. Then, as part of that conversation, we’re going to try to pull out of them, “What are the other challenges that you’re having? What are some things that you’ve thought about doing that you haven’t done yet?”

There’s a huge area of educational technology. Ways that you can leverage technology for instruction. There’s learning management systems. There’s all kinds of stuff. Rather than making the process drag out for a very long time because it is hard to communicate with the people that run schools, because they’re very focused on the education side and not focused as much on us. It’s not as simple as sending them an email and they’re going to give us back 20 answers today. We might have to have five follow up conversations to get a couple answers about these specific things.

So, we’re trying to make it a tight amount of information needed up front, and then most of that information gathering happens in that first meeting. We’re coming with an incomplete version of the assessment with what we think they need to do, and then that half hour/hour is when we do even more discovery so we can come back in January/February with what I would consider to be more of a complete assessment.

This is the approach we’re taking with schools specifically, which, I think in the commercial space, what I was used to before, you could probably have those conversations in a pre assessment meeting for an hour and then have the completed assessment in that first main meeting.

It’s just not going to work with schools. They’re comfortable with these three meetings a year. I’m looking at it as discovery, and just a hint of what we’re thinking at that point; and then January is when we come with, “Here’s what we’re thinking.” The timing is perfect because at that point, they haven’t finalized their budgets for the next fiscal year and the E rate funding has not gotten finalized by any stretch. That’s the time when we need to actually be doing the design and giving them quotes. It should work very well.

I’m not coming completely out of left field – we are doing a much more miniature version of this today, again, via spreadsheets without a lot of cybersecurity. So, I’m just adding in a little bit more complexity and a little more structure so I ensure that every client gets their assessment and they all – if I do an NPS survey at the end of the year and talk about, “Did you feel like you got more strategic guidance than you did the year before,” I don’t want to see a single client that says the same or less. It’s got to be more, and they need to feel like they’re getting additional value from what we’re providing.


[Simon] That makes sense. It’s kind of free validation, I would say, in the Fall; and then in January is when you really present the plan. In the plan you’re presenting, do you always focus on that Fall? Or, do you show them a couple of years or a couple of summers in advance?


[Bryan] Our goal is to do three years out. If a client wants to see five, we have the ability to do that from the asset perspective, but it’s a little bit harder to think that far out in terms of other infrastructure projects because again, these schools can change. Someone could just have a high school and then they add a middle school, but then they could lose the middle school because they don’t have enough enrollment and they close. Then, they could start it up again at some point. It’s hard to look out more than three years, so, our goal is to look at three years. The biggest focus is the upcoming fiscal year, but we want to do at least three years.


[Simon] Who are you meeting on the school side? Who’s your point of contact normally?


[Bryan] For most, it depends. There’s probably a couple of different variations with the schools.

In some cases, if it’s a very small school, it could be the actual head of school, which is the equivalent of the C.E.O, but there is often someone who has the title of director of operations, who’s effectively aligned below the head of school, that knows everything that’s going on, is not directly involved in instruction, and is our point of contact normally.

As you get into larger schools, they’re called networks. You’ll have shared resources across multiple high schools, middle schools, elementary schools, and sometimes you have a director of operations, but you’ll have more specialized business titles. You’ll have a CFO. You’ll have a head of strategy, chief strategy officer type person.

So, it depends on the size of the client. Similar to when I was in the commercial space where you’re working with an office manager, you’re working with the CEO at a smaller one and then bigger ones you could have a Director of I.T. and I.T. Manager in a co-managed set up. We do have some clients that are co-managed, where we’re interacting with an I.T. Manager and I.T. Director. We deal with both.


[Simon] In terms of your process, is it similar, like, the three meetings, the audit, the budget, the three year budget, is this something you do for all your clients, or is it different for smaller schools than the bigger schools, the co-managed… etc.?


[Bryan] We do have segmenting with our clients in terms of our overall touches, just in terms of client management. For the purpose of the assessment, we’re expecting to do it the same for everyone in terms of those three meetings, but those are the three strategic meetings. For larger clients, we do have much more recurring – most of the clients that are of a certain size have monthly meetings, sometimes biweekly, sometimes weekly, meetings.

Our largest clients have weekly meetings with their client manager because there’s so much stuff going on between different projects and new site builds. My preference is that these meetings, these three time of year meetings should not be tactical. They do end up becoming a little bit tactical because, like I mentioned before, they don’t have – our client contacts don’t have a lot of time because, again, they’re very busy with trying to keep the schools running, to spend an hour with us offhand to just talk about stuff.

They do tend to be very focused, so we will get into some of these meetings that we want to be strategic, and we have to carve out some time in the beginning to give them some space to vent. If they want to vent about things that have gone on, either with technology or just what they’re dealing with at a school, to then hopefully draw them back into the main topic of the meeting… which is, all of this work we prepared for you to keep your school up and running, to improve how you work with your students or scholars. It is a hard task. Some clients are better at it than others. I know everyone’s trying, but we do have to adjust our approach based on the client personalities.


[Simon] I agree with you. It’s so important to get the tactical stuff out of the way. Ideally, before that meeting.


[Bryan] Yeah.


[Simon] To make sure you can focus on it.


[Bryan] That would be ideal before the meeting. There are some clients that we’re able to do that, but when we designed everything going into the final one in the spring, there was an immediate pushback internally of, we need to give clients a little bit more space.

I was like, “Can’t we just peel these conversations out?” and they said, “Well, we may not talk to that client since that last meeting, even if we try, because they just have so much going on.” So, we make it an hour-long meeting and we assume that we’re going to lose about 15 to 20 minutes. We really have 40 minutes of actual time, if we’re lucky. Sometimes we may only get a half hour and we lose 20 minutes to tactical, so we may only have 10 minutes. We have to be very focused in our approach.


[Simon] Right. So, what would you say are your biggest challenges today in delivering strategic meetings, for you managing the team?


[Bryan] I think the biggest challenges that we have in terms of delivery… quality of information is a big challenge. At an MSP, you’re always reliant, especially in client management, your response, your ability to deliver quality reports is very much dependent on the quality of the information going into the system.

So… are your project engineers inputting the assets properly as is operations inputting purchase dates? Do you have a proper tool to bring in proper purchase and expiration dates on the stuff that you can’t just, know coming in the door? If you don’t have good information, the whole process of building out those reports can be very challenging.

Because this is something that we’re doing outside of the normal day to day stuff that a client manager has to do, we want to be efficient with our time. If we can spend an hour and a half to two hours building the report, that’s great. If we have to spend three days, because we’re trying to track down assets – printers that should be in the system, but aren’t showing up, we don’t know where they are… That can be a huge challenge. So, quality of information is very important. I will say, CTS does a very good job at it. They’ve had good controls for a long time. I walked into a place that had better documentation than any other MSP I’ve either worked with or was in peer groups with, so I’m very happy about that part.

I think the other piece that’s challenging is our Client Managers – people in client management want to serve our clients and want to serve the community. We’re very mission driven as an organization, but client management is a sales role. Even if you don’t want to call it that, there is an element of you want clients to do things. First and foremost, because it’s good for them as a business, but second-most because we need to continue to drive revenue in order to pay for people to do this job. So, it is definitely a challenge to have a team that is very much focused on the health of their clients and the health of the organization to think about money and it’s not in some people’s DNA; but I give my team a lot of credit because- I’ve pushed on this a little bit since I’ve been here that I don’t want us to have quotas and to be too focused on forecasts and those types of words, like a sales organization, but it has to at least be in the back of your mind when you’re having conversations with a client that they have to keep doing more work.

Financially, we have to continue to have them making investments. If they don’t make those investments, it will hurt the company in other ways, including if they don’t upgrade the switches, and then the switches are old, and then the switches fail, and then we have to spend more hours than we were expecting for a client. That affects your service team, that affects your projects team, your NOC team. So, as soon as client management stops doing what they need to be doing, it will affect every other part of the organization and it affects revenue.

I don’t want to say that client strategy client management is the most important part of an MSP. Everyone is important, but it is a part of an organization that often is not felt to be as important because they’re not actually putting hours against the client’s agreement sometimes. At the end of the day relationships are key with MSPs. You and I both know because we’ve been in this for a long time. You don’t get a lot of clients from just cold calling.

You get clients from relationships. You get referrals. That’s where clients tend to come from. So, it’s very important that you have a strong relationship. That you’re talking to your clients all the time. That you’re keeping their pulse. The sales aspect is another very large challenge that I’m facing. I don’t want to pivot people too hard into sales, but that aspect of things is very important and it’s just an adjustment.


[Simon] Yeah. I couldn’t agree more in terms the importance of strategic services, but I find, or I’ve found, that if you have your standards clearly defined and that they’re really well explained internally – so, in this case, that your Client Managers understand why your client needs to be up to par, I find in that case, then it’s not a sales job for them.

It’s more just taking care of the clients; and then these sales just kind of happened in this case. And the Client Managers are happy to do it because they’re taking care of their clients and making sure they’re up to par. So, in my opinion, it comes down to having well defined standards and also explaining those standards, and people realize why their clients need that. I think it kind of works itself.


[Bryan] Again, you look at yourself as a consultant rather than a salesperson. You’re consulting your clients and you’re telling them what’s the right for their business. And is there an aspect of that that involves them purchasing things and making investments? Yes, but that’s – the focal point is not to tell them to do something that they shouldn’t do just to make a quota.


[Simon] What kind of training or, it doesn’t have to be like formal training, but do you do any training for your Client Managers to give them visibility on what downtime looks like for the client? What, basically not doing the things you’re doing, what are the impacts? I found that sometimes, and I’m equating them to account managers, which they sort of are.


[Bryan] Yeah.


[Simon] I think sometimes a big part of it is them understanding their client, what kind of business they’re in, what kind of revenue they’re doing every single day and what, for example, you’re talking about a switch, right? Like, what does a switch failure look like and how much of a problem is that? Versus, I think a lot of them don’t really, sometimes they look at just the number, and it’s hard for them to internalize. So, things that we’ve done in the past is say, well, this client does this amount of revenue of a day, and try to really have them understand what that looks like and why we propose for them to change, for example, a switch.


[Bryan] Yeah, listen, I agree. For certain things when we’re doing the assessments, we show clients the “Why is this important?” side and that helps. I think the challenge is, when it comes to asset replacements, it’s very hard to do quantitative assessments like: what is the actual dollars lost from a switch being down for X amount of time?

I’ve seen companies try to quantify it and it tends to be a lot of fuzzy math. For example, your firewall goes down, you’re going to lose 50,000… so spending an extra 4,000 on a HA firewall is worth it in theory, if that was iron-clad math. There are supporting examples, that you could get a client to do, but it tends to be a lot more circumstantial. I had a client one time – and, telling of stories is one of the most critical things in being in a sales role, but especially being a vCIO.

The examples that I’m running into now, because we’re pushing very hard with cybersecurity, it’s become a very challenging area in in in the education space. The Department of Education, New York City had a breach in June, and there’s been a lot of schools – there’s been charter schools that have closed down because they’ve had massive data breaches because they’re running on shoestring budgets in some cases and trying very hard to keep everything afloat. Having something that impacts instruction and impacts it for multiple days can be death knell of a business, but we’re telling those stories.

It’s less: “I’m going to spend 1000 a month on some cybersecurity protection. It’s not I’m not getting anything from that 1000.” – in the mind of the client. So, you have to explain: “Here are things that can happen that are more likely to happen. Not- we don’t stop anything. Everything is just, you know, layers of security. We can’t stop it. But, you are much less likely to have one of these five things happen.”

Depending on where their mindset is, they can go, “Oh, okay. I don’t want that to happen. What do I need to do?” And if there’s a trust factor there, then it’s less of a sales pitch. It’s more like, you’re the one that knows how to stop this. How do I best stop this?

Again, all this goes back to the relationship. You have to have strong relationships so they trust you to not have to nickel and dime on something. “What are you saying is the right thing to do? What have you researched, and you believe we should be doing based on all of your experience?”


[Simon] Yeah, it’s funny. In terms of quantifying events, I think as an MSP, we shouldn’t do that. I think the client should do it. It’s more, you know, the conversation. It’s to bring the conversation, right? It’s to say, “Hey, if this happens. It’ll take us this amount of time to bring you back up. What does that look like for you?” and get those numbers from the client. Not us bringing them forward.

As the Client Managers or account managers do that, then they start to learn more about the business and realize, “Wow, okay, this is important because the client is telling them if I am down for this amount of time, this represents X amount. It’s a huge deal.” and I think that helps them get over seeing themselves as salespeople. They’re like, “Okay, no, I’m really helping the client. I hadn’t realized how big of a deal it is.” In the conversation with the clients, you were saying there’s some questions they ask. We have them run through those kinds of things; like, “Hey, if this happens, what’s the impact to you, how much is it going to cost?” It’s funny because a big benefit to it is that our people learn these impacts and then they’re able to do a better job, but also be more convinced that, “Oh, yeah, my client really does need this like we have to-”


[Bryan] You do need to make sure, in those conversations, that you are talking to someone that’s a controller or CFO because in my in my past, when I worked with commercial clients, when you worked with a CFO, you could use that type of analysis the way you’re describing; and it would immediately hit. Again, me learning this education space more, a lot of these smaller schools don’t have anyone that’s really business savvy.

The person who started the school was a former teacher that had a passion and a vision, and they hired school people around them. There isn’t anyone that really has that business mindset, they are just focused on cost being down. The positive is that, as those schools get bigger and they become networks and they have multiple schools, they tend to then hire more business type people that sit in between the instructional people and the head of school. Those people do understand.

Those are the ones we’ve been having sign off on cybersecurity. It’s those people, in upper-middle management, that get it and are able to communicate the message back to the head of school to say, “We need to do this.” We’re getting a lot of yeses when it comes to the cyber stuff, which I’m very happy to see move forward.

The other thing that’s helping is cyber insurance. We could spend a whole conversation talking about what cyber insurance has done, because it’s a negative, but it’s also a positive for our business in that schools have needed to do that. Everyone has and should be doing that. They’re now getting told they need to do it. Thankfully, it’s happening, because otherwise there would be a lot more excuses why they can’t do it. Once they do it, then it’s just part of the budget and it’s expected, and now they are more secure than they would have been if they didn’t have MFA on their email system, or so many other things.


[Simon] I think those insurance requirements will, keep being more and more requirements for sure.


[Bryan] The regulatory stuff that comes from Canada and the U.S., there’s a lot of federal standards that are starting to come down around data privacy. So, it’s only going to get-


[Simon] There’s not going to be less.


[Bryan] That is true.


[Simon] All right. So, if we speak a bit about Propel, how do you use it? What do you see as the main benefits, for you and your clients?


[Bryan] For a very brief history, I worked with Propel at my last place. I brought Propel in there and I got to see Propel when it was in its infancy many years ago.

I don’t know if it was called Propel then, but as soon as I knew that it was a thing that we could get, I got it in place at my last place. As soon as I came into here a couple months ago, I brought it in. We use it for a couple different functions. First, the audit function.

The first part of our overall quarterly process is doing that audit. We leverage it mostly around cyber security. There’s also an infrastructure component there where we’re asking specific questions around, “Do they have security awareness training? Do they have SPF / DKIM / DMARK records?” I could go down the list. We have about 40 to 45 different items that we hit as part of that audit.

Then, we leverage the life cycle tracking of assets. Predicting costs and then tying them to projects. Our whole quarterly process is built around Propel. Without it, we would be back in spreadsheets. Now, we’re starting to leverage Propel for prospects.

We’ve done a cyber, a couple cybersecurity assessments for prospects that in many cases will then turn into actual clients later. So, we’re leveraging it as our presentation tool and our tool to effectively analyze the client’s environment and their risks. We’re not using it to do a true risk assessment per-se, where we’re doing quantitative, qualitative type risk tracking. It’s more of just a controls assessment. Are they doing these ten things that we believe they should be doing, based on NIST, CIS, whatever, and it’s worked really well for that.

The other thing that has helped a lot lately is the feature you guys added in where you can track across multiple clients and look at things like, “How did everyone answer the question around M.F.A?”

That has a ton of value because that allows us to look at the clients that have the gaps and we can create more coordinated campaigns to clients that don’t have backup for Google or Office 365. Yes, we’re identifying it in the assessment, but also being able to then go, “Okay, so we have 20 that don’t do it, 30 that do it. Let’s create a campaign and ConnectWise and reach out to clients outside of the normal client management cadence to hit them with reasons why they should do it.”

Maybe they come back to us and say, “Hey, I saw this thing. I know you mentioned on the last assessment. I think we should do it now that I’ve seen more about it.” So, that’s definitely been a lot of help to us.


[Simon] One last question. What do you see as the future of strategic services right now?


[Bryan] There’s two main areas that I see coming into play. One is the in commercial area, you’d call it the digital transformation type stuff, but in education, it’s the educational technology. So basically, I look at it as, once you get your clients secured and running well and optimized, what else can you be using to improve how the business runs or how your outcomes with your students?

There’s a lot of tech that’s out there and most MSPs are more reactive than proactive. I think that’s the step. Once we feel like we have our clients in a really strong cadence, I want to start expanding more into the educational technology. What are ways that we can improve how their actual business runs using technology? The accounting systems, the CRM systems, the workflow systems using, Power Automate, Zapier, and stuff like that. So, I see that as a big next thing when it comes to vCIO services.

The other is client portals in general. How we present this information today is more of a report we’re creating and physically handing it to them. Then, they’re absorbing it. As the types of clients start to move towards these newer generations of kids as the kids become the bosses, people like to have things more self-service. I can see things starting to move towards, “I don’t want you to give me a report. I want to be able to just log into a system, see what my issues are, and I’ll tell you what I need.” The Uber/Door Dash type thing.

I don’t think there are any systems yet that are there, but I think as things evolve, we’ll start to look to find ways of taking the information that’s coming out of Propel and ConnectWise and finding ways to serve it to clients where they can log in themselves and find the information. And then, they feel like they’re a little bit – it’s more of a co-managed thing where they’re involved in it and we’re helping to provide the expertise and best practices; but they feel like they’re part of the decision making a little bit more up front. So, I think that’s another piece that will evolve. It may not be this year, but I don’t think it’s that far away.


[Simon] Yeah, I agree with you on both those points. That’s awesome. Thank you so much, Brian, for the insights and taking time today to chat. Really appreciate it.


[Bryan] You got it. Thanks, Simon.


[Simon] Thank you.

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