Latest / Career Catalyst / Episode 5: David Maynard how MSP's are Evolving in 2026

Transcript

Episode 5: David Maynard how MSP's are Evolving in 2026 · Career Catalyst

• Derek: Well, thanks ⁓ for joining ⁓ This is of the early episodes ⁓ of ⁓ podcast here. And ⁓ as I explained to you, ⁓ it's really focused on careers in technology and IT. And you have had ⁓ quite an expansive career. You've filled quite a few different roles. Maybe we could actually just start with a brief introduction and hear a little bit about your journey through your career path and sort of who you are and what you're doing currently. Dave Maynard: Yeah, so my name is Dave Maynard. ⁓ My official title is CEO of a little IT consulting MSP called Syntax here in St. Paul, Minnesota. ⁓ I more think of myself as the chief nerd though, among our team. I got started in my career in high school actually. There was an innovative program at my high school where I did a work study in the afternoon and I took care of the K through 12 media center computer labs. So that was my first job. as a senior, had, it was 1995, 96. So we had various amounts of really old 8088 computers from the early 90s up to 386s. And it was through that program that I learned a lot about Novell and networking and putting in ethernet cards, stringing cables through the school district. And that kind of launched my career. So right after high school, I got hired by one of the firms that was helping us out and did some IT consulting through mid Michigan, through various school districts. And then I had an opportunity to join a defense contractor out in San Diego where I did Lotus Notes and Novell administration. And all on the way through my career, I had lots of amazing mentors that kind of, I've kind of learned on the fly. Yeah. Derek: That's important, yeah. The mentors are important. Dave Maynard: That and certifications, know, along the way I did Novell certifications, I did Lotus Notes training at the time, basic networking, ⁓ studying up on protocols and functionality. After that, I ended up moving back to Michigan and discovered Citrix in the late 90s. And that kind of launched, I would say, the biggest part of my career, because to make Citrix work well, you have to know all the other aspects, firewall, core networking, server storage, infrastructure. ⁓ performance and everything affects the Citrix session. So I really got to dig in and work throughout lots of small, medium sized customers to large enterprise as I moved around, still staying technical or very technical in my role. I ended up in Minnesota through a job change and fell in love with the Twin Cities here and worked with lots of amazing companies. And that's when I started at Syntax in 2004. So I worked here for 10 years, and then we had a ⁓ family move out to LA. And so I had some various roles out there, mostly consulting and then ended up in a leadership role with you, Derek, at the law firm we were at together. And ⁓ I was at that point in my career where I was trying to decide, you know, after 20, 25 years in technology, the technology that we're using at the time doesn't align, isn't anywhere close to what we had when I started my career. So it's this mid-career path of which direction do I go? Do I go more leadership role, you know, role, or do I say super technical? Do I go more architectural? You know, I'm still figuring that out, but now, you know, now in my new role, I've kind of, went more leadership and, still with some technical and then I swung back to architectural and I had the opportunity after moving back to Minnesota to, you know, my mentor who started Syntax 40 years ago is retiring. So. I ended up buying his shares and taking over the leadership, but still staying technical here at our small ⁓ IT managed service provider. Derek: Very cool. Well, as I said, you've definitely kind of had your hands on a lot of different technologies. ⁓ You mentioned you sort of started in a very kind of entry level role ⁓ when you were still a student even. ⁓ Do you think that that career path is still available? And is it still desirable? There's all these other sort of ways to get into technology now, whether that's know, code boot camps or comp sci degrees or, you know, starting a different sort of entry point certifications, et cetera. ⁓ I'm curious what you think is the, you know, valid career path or best career path in 2026 compared to how you did it or is that still a completely valid ⁓ opportunity path? Dave Maynard: I think it is still a valid path. think there's, like you said, there are multiple ways that you can launch a career and they all have their pros and cons. I think it depends on the individual and their learning style. For me, I'm a very hands-on learning style person and you know, at the time, there weren't degrees that align with that. Like you said, there definitely are more now. So I think for a student such as myself, there's a bit of better chance that you could go into university or something like that kind of program to get launched and you'd learn kind of other, the full scale, full picture that, you know, I didn't have just starting out and working and being very technical focused. ⁓ I do think both are good options or, you know, all the avenues, whether it's a coding bootcamp, if you want to be on the more programming side or doing a, you know, a college degree focus on ⁓ technical because all that does apply. And I think the biggest aspect is finding a way to get some real world experience and, you know, working with mentors, whichever avenue you go is kind of getting that first job, that first opportunity to really dig in in an environment. Cause that's where all your training, however you do your training comes together and helps. ⁓ think somebody as an individual figure out what excites them and what they want to focus on, as well as build those skills that employees are looking for. Derek: You know, I was about to ask you, you're a CEO now, so if somebody's out there trying to get hired, what should they do to get hired? But I think maybe you almost just answered that in your last answer, which is having a mentor, right? Having sort of a champion who's gonna help you along your journey. I think in many respects that's more important than ever, right? I mean, we're hearing from some of the other guests that we've talked to that even students at great universities are having trouble with internships and with their first job, right? And a lot of other people who are caught up in layoffs, et cetera, are also experiencing some challenges. And so I think having a champion or a network of people who are behind you ⁓ is really important. But I am curious, what are the kind of skills that you're looking for these days when you think of hiring sort of either an early or kind of mid-career employee? Dave Maynard: So I've been thinking about that this week kind leading up to this interview because I was, you know, a few weeks ago I was visiting some old friends and we were all around a dinner table together and we were all joking that we had paper outs when we were young, you know, because we, none of us had any money and, you know, we had to start working out, you know, working soon, ⁓ as soon as we could. And we had that desire and drive. And one thing that stuck, yes. ⁓ Derek: We might have to explain what a paper route is to some of the Gen Zs, but yeah, go on, yeah. ⁓ Dave Maynard: Yes, I at 5am I woke up and rolled a bunch of newspapers and shoved them in a bag and rode around in the snow and threw them on people's porches. but I also use that as an opportunity to do my first form letter using word processor on my Commodore 64 to notify my customers when I'd be going on vacation and that yielded extra tips and stuff like that because I did a mail merge and you know, so I kind of made it my own way with some nerdy aspects but but what Derek: Hahaha There you go, yeah. Dave Maynard: settled, like what really hit home for me in that conversation was drive and grit and ownership. When I think of what I'm looking for in a candidate or how I'm looking to coach and mentor my employees is taking ownership of something. If a customer has an issue, and that could be, you know, a customer, a consulting customer, or just an end user, I like to consider them customers. If they have an issue, I Derek: Mm. Mm. Mm. Dave Maynard: I would like to see somebody take ownership of that and complete it to the end, provide updates, really dig in if it's something they can figure out. Great. If not, know where to go to ask for help, but still be the face to the customer and updating them so they know that issue. And then I also like to see drive. If I think anybody who has an aptitude for technology, an understanding of basic troubleshooting methodology, especially now that we have Google and we have AI and we have all these incredible search utilities and tools and YouTube videos that we didn't have early in our career. I think as long as you have that hunger and the excitement and the aptitude for technology, that it doesn't really matter the platform that somebody can figure it out given just a little time and research and the right ⁓ support to ask for help. And those are the big things that I look for is people who can... be customer service oriented and really ⁓ learn and dig in and figure out and uncover all the layers and figure out why the problem happened versus guessing and trying to find a solution. If you can really peel back the layers of the technology and understand where the communication broke down, where the problem happened, that helps you in the next hundred issues you have, because you better understand that technology stack. Derek: Mm-hmm. You know, I think it's a really interesting answer and frankly not one that I expected. ⁓ But you know, those are all in many respects sort of soft skills, right? Drive, grit, ownership, et cetera. They're not, you know, ⁓ I know the TCP stack or you know, I'm really good at PowerShell or you know, really technical stuff. And I think you're onto something, right? Because we are in an era where the answers to those more technical questions Dave Maynard: Yeah. Derek: questions by and large are just a prompt away, a super quick look up, right, et cetera. And so I think in many respects, the deep technical knowledge, it's still great, it's still something people should strive for. But you're right, that a lot of what employers nowadays are looking for are people and personalities where you are going to really problem solve, you're gonna drive to a solution, as you said, own it, right, ownership. ⁓ I think those are all incredibly good points, right? And they serve people throughout their career, right? mean, whether you're at the very, very beginning or at the Dave Maynard: Yeah. Derek: CEO, those traits are still useful. Dave Maynard: for sure. Yeah, and the technology, the technical skill set is still really important, but I think it's more that it sets what level of the stack you're going to be working in, whether you're at the workstation endpoint level where you're core networking, whether you're server cloud, cloud native development. think you have the technology to me and your technical aptitude kind of puts you in that spot. But these soft skills, I think, are the most important thing as long as you have one of those technical avenues or the aptitude willingness to learn one of those avenues. ⁓ Because we all need to be technical first, but those soft skills that I mentioned, I think, are equally as important and probably more important for having a long-term employee and someone who can rock it up in their career. Derek: Yeah. So I'm curious, ⁓ how do you think AI is changing things, or is AI changing things? When you think about your employees, your ⁓ customers, is it a big part of your day to day yet? Is it starting to be? And where do you think we'll be in a couple of years or a few years? Dave Maynard: That's a hard one to answer. It feels like everything's changing and I don't know if anybody knows or I certainly don't know what it's going to look like in five years. What's been happening for me and my team is it helps streamline troubleshooting and searching as well as things that are documented to... Derek: Mm-hmm. Dave Maynard: query existing documents. That's why I like to think there's a lot of Microsoft licensing nuance, and Copilot can answer all of that versus looking at a matrix. So it's more like speeding up questions and answer finding when engaging in sales calls and prep for sales meetings on that side. On the technical side, I know how to speak things out in DOS command prompt, and I don't have to think for a second. I could just... Derek: Mm-hmm. Dave Maynard: come out into the keyboard, I can pop that in and it can spit out PowerShell. Like any kind of translation. ⁓ And then just general troubleshooting, like the ability to paste in screenshots of error messages and have the AI tools read and interpret that versus having to type out what the error message is and the 0x8f blah, blah, blah error code. Like that, think, is sped up our ability to get the information to point us in the next direction. Derek: Mm-hmm. Dave Maynard: But I haven't seen it yet, you know, entirely solve problems. Customer has a problem, you put in the screenshot, it's going to get you closer. Maybe it'll solve it. It's, yep, exactly. So I still see there's a ⁓ really deep need for understanding, okay, the search results sent me these articles. This is where I need to go to dig deeper and understand where I can fix the problem. And sometimes it gets it right and it's just fixed, but not all the time. Derek: It's not end to end basically. Yeah. Yeah. Right, that's kind of been my experience. I've played with it a bit. There's Copilot now, for example, built into the Azure, ⁓ Entra, overall M365 Microsoft ⁓ consoles, admin consoles. And it can occasionally of point you in the right direction or point out a configuration that isn't quite right. ⁓ But I haven't really seen it sort of end to end. fix things yet. I could certainly see it heading in that direction and that would change a lot of ⁓ jobs even more, but so far ⁓ it hasn't really exactly done that for me. ⁓ I'm curious for sort of maybe, Dave Maynard: Yeah. Derek: More mid-career folks, ⁓ are there particular certifications or training pathways that you think are most valuable right now? Dave Maynard: Oh, I would say anything cloud, whether you're looking at the cloud native, you know, platform as a search, platform as a service certs or stack, or infrastructure as a service, whether it's Azure, AWS or GCP. I think any of those, because I, you know, I've, was an instructor for many years for Citrix courses as well. So I took a lot of tests and a lot of certifications back then. And Derek: Mm-hmm. Dave Maynard: Every time I did one, whether I wanted to do it or whether I had to do it, at the end, I learned a lot of good pieces of information, good nuggets that I didn't know before. And so I think going down the certification path of anything cloud, anything, pick your, your passion. Basically, I think those are all good things because it shows employers one that you have the credentials, but two that you went through the exercise and, ⁓ learn some, some new interesting things. Derek: Mm-hmm. Right. Dave Maynard: on those stacks. Derek: Well, and speaking of grit, you mentioned that earlier. It does take a little bit of grit, especially for folks who have families or day jobs or just other things going on in their lives, to sit down, find the time, take some concentration to get through some of those, the material and the ones with exams and so forth. to your point, if you're able to get to the end of that and get the certificate, it does kind of show an employer that you're willing and able to do that. And I think that even if it's not the exact technology that the employer is most interested in, ⁓ I think it does kind of show that there's something there that most employers value. Yeah, yeah. So in terms of ⁓ where you sort of see technology stacks, Dave Maynard: Yeah. Yeah. Derek: evolving, there's been a little bit of discussion that I've heard of clouds becoming too expensive and actually some workloads moving back on-prem. I'm curious if you've seen any of that or if you think really the long-term trend is just to kind of have everything transition into the cloud. Dave Maynard: Yeah, I've seen both. I've helped customers migrate to the cloud. I've also helped ⁓ customers migrate back to on-premises data centers. ⁓ The end result for, I think, a lot of people is somewhat of a hybrid, whether you have on-premises resources for your primary compute and then use the cloud for backup, because that's a much more cost-effective way to do disaster recovery planning, ⁓ warm backup sites. ⁓ And we service a lot of small medium sized customers. And some of those, it was really easy to get up to the cloud and it made financial sense. And some of them it was much easier to stay local. So I think it depends really on your workload, your application set, and really analyzing what that compute is gonna cost in the cloud long-term and using that to make a decision. If you're able to refactor your applications into more of a cloud native where you're running serverless and can leverage all the cloud native functionality, that has a much better long-term ⁓ cost effectiveness than if you just lift all your servers, ⁓ all your old clunky servers from your data center and plop them into a cloud. And since that's usually the most expensive way to do it. Derek: Yeah. Yeah. Dave Maynard: And there might be practical reasons where that makes sense. If you're closing a data center, that's really expensive, or moving buildings, something like that. Those are good reasons to go to the cloud like that and then slowly transform after you get there. Derek: Yeah. A couple more quick questions about career paths. You have had largely an engineering role and a hands-on technical role, kind of an architecture level role for much of your career. ⁓ But you've also kind of had a sales role, or at least sort of a sales engineering kind of role, working for MSPs. I'm curious if you could compare and contrast sort of the sales component of your job versus the technical component. What are some of the pros and cons? Because there's a very valid career path that I think some people overlook of sort of sales engineering or technology sales. A lot of people make a lot of money doing that. Dave Maynard: Mm-hmm. Derek: Talk about that for a couple of minutes. Dave Maynard: Yeah, so it's been ⁓ one of my favorite parts of my job over the years. And I'd say in most of my roles, the last 20 years have had some type of sales engineering component. I've never been 100 % full-time sales engineer. So if you work for a larger vendor or reseller or VAR, then there are those 100 % sales engineer roles. Mine has been more of a component. So I think both paths are really valid. For me, I like still doing the build aspect because I think that makes me more effective as a sales engineer because I can really come to the customer with solutions. And that's the biggest thing is when you're in a sales meeting, whether it's in person or virtual, the ability to listen to the customer and the fun part is hear their business challenges and then be able to map that to some technical solution that you can come up with. And the audience is everything from the nerdiest of nerd, the most technical person up to the C-level executive and having the ability to translate that across those layers, the technology that you're talking about that's going to solve that problem is a real fun and interesting challenge. So I think, you know, if, you know, some technical people ⁓ want to just focus on the technology, they don't thrive on, you know, interaction one-to-one with other people. in general, like they just want to focus on their work, get really technical and kind of do that in the background. And I think that's ⁓ a really great career path for people who want to stay technical. I would say for anybody who's technical and likes to talk and likes to hang out with people, ⁓ maybe more extroverted or maybe an introvert who likes to be extroverted sometimes like me, ⁓ it'd be a great path to leverage both your technology skillset. as well as your people skills and chatting with people. ⁓ And just really, the biggest thing is just seeking to understand what challenges they have and taking from your breadth of technology experience to say, I know this software, I know that we could build it this way. And whiteboarding, demonstrating what you could do for the customer is a really fun part of that role. And as you said, it's a great opportunity because ⁓ If you do make a sale, know, some roles are partly based on commission or a part of that, ⁓ you know, usually sales engineering versus a peer sales is more based than commission, usually 80-20, 70-30 split, you know, 70 base or 80 base and 20 or 30 commission respectively. So it's a great way that, you know, if you do a good job and if you, you know, sell a great solution that you can kind of have a little more control over. Derek: Mm hmm. Dave Maynard: how much money you're making long term ⁓ by driving more sales and in a way that shows value to customers so that they keep coming back. Derek: Great. Well, last question. ⁓ So I know you're CEO of an MSP now, so maybe you're a little bit biased. But talk to me a little bit about the pros and cons or the differences of working for an MSP versus working directly for a corporation or a company. Dave Maynard: Yeah, so I've done both. ⁓ I've mostly been at a MSP or consulting provider. For me, I love the variety that that brings because if you're working for a service provider, whether it's managed service or professional service, then you get to see a lot of different customer environments, which helps bring new challenges and you get to see, ⁓ this is broken here. And then six months later, you can remember, ⁓ I had this fixed over this other customer, or this works well for them. I can share that with this other customer. And so you get to, for me, I get to learn a lot and really be in a bunch of different environments, which helps me and kind of, I like variety, just as my personality. So that gives me the variety that I crave to really ⁓ kind of get me excited. I've also been in roles where I had ownership because then one of the negatives is you in MSP you have a little more ownership if it's the same environment we're managing. You know, we have our pool of customers that we own, there certain aspects that we manage. But, you know, when I've been full in house and I get to own it, which means I get to build all the stuff the way I want and follow my vision from end to end. And so I think, you know, when you work for a corporation, you know, as an internal IT support or architect, you really get to, have that ownership and build it your way and ⁓ which is good and bad. means when it's broken, it's you who they call and ⁓ but you can build it in a way that it stays stable and have more fun with that kind of internal ownership. Derek: Right. So Dave, we've talked about a lot of topics. ⁓ If you were to sort of sum it up, if you had a little bit of advice for folks that are maybe looking for a new job in this environment, or perhaps they're in a job, but they're kind of considering, is this the right place for me to stay for the next few years? ⁓ What's your advice in 2026? Dave Maynard: ⁓ I'll start kind of with the back end of that question. You know, if somebody's in a job and maybe they're not excited, not challenged, and they are looking for something else, I, you know, I was with Syntax 10 years before we moved west. And I think you don't stay with a company more than a handful of years without really strong communication with leadership. And in those 10 years, I would always say, hey, I'm bored with this, or I want to do this, or I'm excited about that. I would say, For people who are in a spot, I would say start internal first and just have a conversation and talk about what excites you or talk about what solutions you feel you can bring to the organization. If you don't get positive feedback, then it's, I think, a good time to look external. And if you're looking external, whether for job seekers ⁓ across the board, having a new certification, having... ⁓ the ability to network, looking for end user groups or community events. Because, you know, if we submit resumes, it's hard to know if that reaches a human. And if a human gets it, they have a minute or so glancing over. So it's really kind of a luck of the draw when you're just submitting resumes blindly is if you're going to get to have a conversation with somebody. any way that you can network in your community, ⁓ Derek: Mm-hmm. Dave Maynard: go to events, you know, if there's a company that you really, you know, want to work for, find a few people on LinkedIn and just, you know, send them a message saying, Hey, I really love your company. I want to find a role like what you're doing. Is there any way you'd be willing to chat with me? And it might, it may or may not lead you to a referral, but at least you'll get some more insight and you know, meet a new person. So I, I would say it comes back to networking and having, you know, a shiny new certification will just be gravy on top, think. Derek: Great. Well, that's great advice. Well, thank you so much, Dave. It was great talking to you, and hopefully we'll have you on again soon. Yeah. Dave Maynard: Yes, thanks so much. Have a great day.