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Building Strong Vendor Relationships in IT Leadership

NinjaOne
08/04/2026
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Today we're going to be talking about vendor relationships and how you can make the most out of, you know, the whole software and hardware procurement process, making relationships with vendors, things like that. And I think it's going to be a good discussion. We might have another panelist joining at some point, but I don't know if there are any technical issues or anything. So for now, we're going to be talking to Clark today. And before I get into everything, in case you're new to the IT Leadership Lab, welcome in. This is a community dedicated to IT leaders. It's a place for you to share content, learn from your peers, build community, things like that. And then we host bi-monthly webinars just like this one to discuss various IT leadership topics. And then we actually bring on leaders within the space that can kind of give their expertise and give you real applicable advice to IT leadership. So Clark, if you want to introduce yourself, I know you've done this a lot of times, so feel free to share some fun facts about yourself that you might not have shared in other streams. Okay. Yeah, yeah. Yeah, so my name is Clark Sandlin. I'm the CEO and president of Zerca, which is a managed IT service provider for private equity, family offices, and high net worth individuals. I've owned my business for 21 years, been in the business for way longer than that, considering retirement very soon within the next five years. Really excited about that, excited about working in a different field, maybe opening up a bookshop or a wine shop or something like that. I don't know, something that's a little bit slower than tech. I actually, so just as a heads up, I kind of shared before we got on, I am actually in two places. I live in Arkansas and I live in Dallas, and right now I'm in Arkansas. So we're about to get a really bad storm. So hopefully my Starlink holds up. But then, you know, I share a lot of time in Dallas. And actually I've been in Dallas a lot this year, and I'll be heading down to Austin in two weeks and then Houston. So I'll be traveling a lot. Anyway, that's me in a nutshell. Awesome. Well, I'm glad to have you on again. I know you've got a lot of experience working with a bunch of different parts of, of it and owning a business and things like that. And I'm sure you have a lot of experience with setting up vendor relationships too. I know that that's a huge, a huge part of your job. So I just want to kind of start out with what the process looks like, kind of in a nutshell, how does it start and what does it look like when the process is So this whole process for me has evolved naturally, you know, naturally been in the business for like 35 plus years. It's evolved, you know, from, Hey, yeah, whatever, let's, let's go. Let's let's do this too. Now we have a formalized process of we have a DDQ that we use. It's a third party due diligence questionnaire. And we've developed this over maybe the past 10, 12 years. And each year we kind of add more to it, but basically it's a questionnaire we send to vendors and, you know, first of all, if they sign off on it, that's a good, you know, a good sign if they fill it out and take the opportunity to address the questions and things like that. But ours is pretty extensive. I shared it in the IT leadership lab. I have a couple of changes that I need to post pretty soon that include AI stuff, but that's our process today. We have a thoroughly documented vendor engagement process, and that's where it starts because it starts the conversation around, you know, a lot of, a lot of detail as far as do you have backups? What's your AI policy? What's your cybersecurity policy? Are you a sock to compliant or, you know, what, what compliance do you fall under? And then that starts, you know, some, some deeper conversations and it, you know, if they can't even start to have that conversation, then that's usually a red flag. Yeah. How do you source the vendors? Like how do you find the vendors that would, that would fit what you're looking for? Is it reviews? Is it peer, peer reviews, things like that? Okay. So usually, you know, I have a network of, of people that I reach out to in the industry and I ask them like, Hey, what are you guys using to solve this problem? You know, how are you working with this? Recently IT leadership lab has been helpful for that as well. I mean, it's, it's great to have these kinds of conversations. I've seen quite a few people pop in and ask questions about vendors and things like that. That's been, you know, very helpful to have those kinds of conversations. So it's nice to have this community as well as a sounding board, because I think it's actually even better because you guys are more tech leaders. Like you've been through the tech. Some of my CEO groups and networking groups are, you know, they're not, yeah, they're, they're CIOs, they're CISOs, but they don't really have that tech. They're more management, they're more business focused and they don't, you know, it's not like they are playing around with mesh tastic on the weekend. So it's nice to have that IT leadership lab. And this is kind of why I've liked, I've really been drawn to it and I've really interacted a lot with you guys because I really like what I, the feedback that I get and seeing the questions that are posted, I'm like, Oh yeah, I'm going through that too. You know, it's, it's nice to know we're not alone. Yeah. Yeah. I mean, I think that's like one of the biggest things about being an IT leader is you, you are on this tightrope between tech and people management. And it's like, you know, it's a very unique balance of two very different things. So yeah, I, I, I completely agree. I'll share my, let me share this real quick. Yeah. Yeah. If you want to share the DDQ document. Yeah. It'd be nice if I didn't have all these tabs open. Oh, no one, no one wants to see the number of tabs that I have open on. And I always, I always like, okay, well I want to save these. So then I'll open new tabs, I'll open a new window. And then suddenly that new window has 20 new tabs. I need to know. All right. So this is the foreboding third-party due diligence questionnaire. And the, the genesis of this, it came out of SEC compliance forms that we developed for our registered investment advisors and private equity and hedge funds. So we built this for them and we're like, Hey, can't, why don't we just apply this to us? So, you know, we have, this might be too much for a lot of people. So, you know, you know, take it remove sections, add sections, but you know, we assess like what needs to be outsourced. You start with the, the type of service or, you know, application or whatever, and then you zero into the financial impact. You know, we go through all these general questions, of course, you know, firm address and who's our point of contact there. And then we get into the, the real core due diligence down here with, you know, as far as what kind of compliance it is. So your, your compliance checkbox check boxes and what they have to adhere to for that. I know, you know, like Tim's for, for example, is, you know, I'm sure he has some specifics as far as how, how he works with nonprofit organizations, you know, a lot of checkbox for them, everybody, you know, this is, you can tailor this to whatever your, your environment is, but then the really meat of it is like, so, so we talk about getting into the contracts and agreements. What does it look like? What are the limitations? How long is it? What's our out? You know, what's the commitment? Then we have oversight, a process for this for periodic review. So in other words, we only do this like annually for us. The register, the SEC requires RIAs, at least private equity to visit this at least annually, but some of them do it even quarterly, you know, kind of a touch base with your account reps and things like that. So then, then we get into the due diligence questionnaires as far as where's your local office, where are you based out of? Because these are all important as far as cybersecurity goes geopolitically, you know, when you want to drill into who really owns this. Like if, you know, for example, like unify ubiquity, unify, like if you really drill into it, yes, they're an American company, but if you drill into it, they're hosted, you know, they're, they're, they're Chinese based. But the corporation is here in the United States. So these are factors you, you know, once you really drill into it, you kind of have to think about it. Okay. We have to think of this as a risk when you get to, you know, geopolitical conflicts and things like that. So, and we get a lot of questions from our customers like that. So then of course we naturally evolved to adding a cybersecurity layer to this drilling into the, you know, the vendors, what are their policies? You know, I want to see, you know, we know what our policies are. We know what our password policies are. We know how we protect our data. We know how we protect our clients' data, but we want to know how our vendors do, because this is very important when you start thinking about like LastPass that was, you know, hacked like three different times and all of it was because a developer was using a VPN at home and he downloaded an app on his phone that gave basically access to the entire LastPass ecosystem. So, you know, those are kind of things you want to know that they have those MDM. Do they have compliance management? Do they have DRP? I'm sorry, DLP, you know, daily protection. And then what is their security protection? So we go into a lot of details and the one I've added, so we've added this, this is the old document, but we've added the AI policy because we want to know who's using AI. Are they using the free version or are they paying for it and privatizing their, you know, their AI infrastructure internally, or are they dumping this information out publicly? This is a very important one for us for transparency, for our clients. They aren't even asking these questions, but we've been asking these questions and our clients are going, Oh wow, we never thought about that. So I'll share that one, you know, later today, but I'll repost it. I went ahead and dropped the link into this doc. You can download it. It's in the chat. If anybody else wants to download it, use it for assessing vendors. I think that's a great like starting point for trying to review vendors, see if they fit everything that you need. And feel free to make comments and share back and like, Oh wow, this, we didn't find this helpful, but we added this, that's always nice. And that's kind of what our community is all about. Let's, let's, you know, I welcome feedback, critical feedback. Yeah, I think it's, it's all like a constant learning process. So just about refining, refining documents, refining resources and making them, you know, work for, for everyone. So whenever you are looking at a vendor and evaluating them, how do you balance between the short-term needs and then long-term strategic fit within the organization? Yeah. So that's, that's a really challenging one. Cause you know, especially, especially with vendors and, and you know, I don't want to knock sales people, but you know, there's always that honeymoon phase. Right. And you know, it depends like, like most more and more vendors are, you know, you're, you're doing a 30 day commit rather than long-term commitments. And that's, that's really important as far as like how, you know, how you approach the whole relationship. So if it's a 30 day commit, Hey, no big deal. You know, you're, Hey, I can get out of this, you know, after 30 days. Yeah. It might, might be painful because you know, whatever the migration process is from what you're currently using to what you're going to be using. And you know, that's that's, but the longer, so we approach the longer term commitments. Like if it's an annual commitment, then it's even worse. Right. So then we're going to really drill down because we always know that honeymoon phase is coming. Not always. We're surprised sometimes by some vendors, but you know, usually it's like the sales guy, Hey, I'm done. I'm out now. Here's the account, account rep, you know, here's your, your tech team, here's your rep representative. And then it's not always a really nice transition. And you know, then you find out, Oh, okay. you find out, okay, we haven't, you know, we're not important We. anymore. We're just now a number. We've transitioned to the number and we're a honeymoon phase. And I've had, well, we'll get into this later, but I've had so many problems with, with vendors in the past. I won't name names, but, or maybe I will. I don't know. Yeah, yeah. Definitely. I hope I answered the question. Yeah, I think so. I also wanted to say hi to Kelly. Welcome in. Thanks for joining. Really appreciate it. I know you had a busy morning. So yeah, welcome in. Do you have any, no, no, you're totally fine. Do you have any thoughts on the vendor kind of evaluation process and then balancing long-term strategic fit with short-term needs? You know, what Clark shared is really great. I never have gotten successfully to the point of systematizing an evaluation. It's been a lot of firefighting. Involuntary vendors are my least favorite, where somebody else in the organization makes a decision and says, yeah, okay, IT, we signed a contract and we spent $100,000. I need you to implement this by next week. Yeah, those are my, but, you know, it, it's a, it's really a learning process. I found, you know, the like, like anything else in leadership, it's a, it's a, it's a trial. You, you, you find the vendors that you trust, both their solution and their people. And, and rarely have I been able to find a vendor that I can just stick with. You know, sometimes it's the third or fourth iteration where, you know, like at my last job, you know, we had just switched Microsoft licensing vendors because, and CDW is just, I don't know if they were ever good, but I've had, I've had decent, decent reps. Yeah. And, but lately it's, it seems like it's gotten worse. Like as they've gone through rounds of layoffs, you know, the, the quality of the rep has gone down. And so, you know, it was just, it was time. It's disruptive. It's hard. I think that's part of the problem. Why it's, you know, with SAS and licensing, sometimes it's really complicated to switch vendors, but yeah, that's, that's the cost of doing business well is being ready to drop somebody that's not ready to partner with you and just wants, just sees you as a revenue source. Yeah, I think to add to this, Kelly is like, yeah, this, this, you know, having this documented process and actually falling through it through with it is like one thing, right. But I think kind of where I've, you know, going back to the beginning where I talked about retirement, right. So where I'm at, it's like, I'm in a mentorship kind of like, you know, the generativity phase, which is why I'm putting these documents out there, because guys, I made thousands and thousands of mistakes. And this is, this is the, the result, you know, I've got this template now of all the thousands and thousands of mistakes I've made, built in and refined. So now I can hand this off to the leadership in my own organization to run, take it and run with it. And hopefully I can share with, you know, you all in the community to at least, I mean, you don't have to go and fill out everything on there because it's kind of intimidating. It's three pages long, right? Well, now it's gonna be four. But, you know, at least it gives you kind of a guideline, because the mistakes I've made has been, man, I just jumped into a vendor relationship quickly, or like you said, CEO comes and says, Hey, guess what we signed up for. And then now you're having to like quickly backtrack and and this this form, when that CEO brings that application to her that that software or that whatever it is, I mean, we've had huge things that just show up. You can give them this and say, well, hey, did we vet this first, because we need to know what their cybersecurity position is, we need to know how they manage cybersecurity internally, we need to know what their AI policy is, because with a lot of leaks nowadays with information, they may have custody of information that you don't want getting out. So it's a good kind of like, hey, let's put this on pause while we vet this, so that we can show here are the risks. And you can usually usually do it pretty quickly. And that's why I like lists. And that's why I like templates like this, you just go down it real quick, because you don't have to reinvent the wheel every single time, which is what I've done for like 20 years. So please learn from my mistakes. Yeah, yeah, as we've discussed earlier, it's all learning process. And it's all trying to figure out what what sticks and you know, it's not going to be one size fits all, some people will use some stuff, some people might need to add stuff depends on the industry depends on what you're looking for. So yeah, definitely, definitely a big learning process. And y'all mentioned, you know, when you're evaluating a vendor, or you bring a vendor on the quality of the reps matters, the support that you get from the vendor matters, obviously, cost matters, how do you balance the need for all of these different things? And do you weight some things more heavily than others during that evaluation process? You know, cost is always the hardest limiter. You know, it's the one that we bounce off of more often than not. But the cost of switching is really high. And, you know, over, over time, I've gotten to the point where I've had to, you know, really value the, the person, the team on the other end, over the cost of the service. So some things, if they're competitive, it's worth, it's worth paying a little bit more for a higher quality support team than than just getting the cheapest thing possible. And that's not always achievable. But man, when when something goes down, and you know that when you call, they're going to answer and they're going to solve your problem. It's worth, you know, this, whatever you spent, that's a little bit more, or maybe not even a little bit more, but it's more than what you could have gotten from, you know, worse, worse support. Yeah, I think, well, back to your point, Kelly, you raised earlier, with all the layoffs in the sales organizations and vendors and things like that, it's getting harder and harder to have those relationships because you know, they keep moving the junior up into your position, and you've been dealing with somebody for, you know, years and then all of a sudden, okay, they've moved them or they've laid them off because of salaries or whatever. That that is, right now, I think that's a bigger challenge than anything else. Because I'm today, I'm just happy if I can get somebody on the phone. You know, kind of like the meme, like, representative, representative. If I can get somebody on the phone, that's great. And I, you know, I really consider that when switching to vendors right now. Yeah, of course, there's always the honeymoon phase with the sales rep person. But, you know, I even fortunately, a lot of these applications now have like 30 to 60 day trials, and you can even extend them further, which is nice, because then you can really test out support is support responsive. Yeah. You know, I love trials, because, you know, that gives you a real opportunity to find out to peek under the hood, even closer and see, okay, do they really have these processes in place? You know, try changing your password, say, Hey, I need help with changing my password and see if they follow cybersecurity parameters. Is it chat help? Or is it phone help? You know, like, what is it? Because, you know, chat help? We all we all know the challenges with chat help. It's nice to have, you know, be able to pick up the phone and talk to somebody. Yeah, yeah, absolutely. Especially when you need to get some things solved quickly. All right. Beth actually asked a question in chat. Anyone else seeing their service reps being rotated annually? They frame it as this individual has been promoted. But for some of our vendors, I've had five reps in three years. Annually, you're lucky. Is that something you're seeing a lot of? A lot. Yeah, like I mentioned that with the layoffs, as Kelly said, you know, Kelly, I guess you're running into this frustration too. But, you know, we've cycled through a lot of account reps. Wow, even one, one firm we cycled through like maybe three or four in a year. Which was insane. Yeah, yeah. I'm seeing it too. And it's it's both sides too. It's the layoffs. And you know that the sales industry is is is motivated by, you know, what's the next good thing. And they're they're incentivized strongly to seek out that. And so, man, when I find a sales guy that salesperson that is, you know, loyal to their organization, it's like, hey, let's exchange cell numbers. Let's, you know, let's let's go do things together. Let's build a relationship because, you know, I want to I want to keep you because you're loyal to your org, which means you're going to be loyal to me if I am not going to mess around, you're not going to mess around. You're making money, I'm getting service. Let's be buddies. Let's not just be, you know, customer and, and salesperson. Yeah. Yeah. And transparency, the one I was referring, I'm sorry, the one I was referring to was Kaseya. So and that was actually maybe four years ago, four or five years ago. But that's the other part of the problem. Like if the vendor gets into this growth phase, and they just start acquiring companies, and, you know, it's a owned by a PE group, that's, that's one of my markers, like if it's owned by a PE group, walk away. Like, like that's I asked Ninja one this at the ITX last year, I was like, Are you guys bringing in PE because that always ruins everything? And they said, Nope, nope, nope, nope. Talk to the president about it. It was like, cool. I'm on board. This is awesome. Of course, he added the caveat. Well, we're not ever gonna like not do it. But you know, as for the near future, we're not and I was like, perfect. I'm on board. And this is what I love. Don't want to like, prop up Ninja one, but they're an amazing vendor because just because of that, right, they're not owned by a PE group, who's constantly combining like, like the Microsoft has done, like Kaseya has done, like, ConnectWise has done just dumping all these products and that don't talk to each other and all the different departments don't talk to each other. And with Kaseya, we had, you know, like, four or five reps in one year, because they were growing so fast, and they kept moving the our rep, which was really good, moving them up into like something else a different role and bringing on somebody new, and throwing them into that role. So that's always a challenge, too. And I don't have that on my DDQ. I should add that are they owned by private equity? So yeah, that that would be a really good thing to add there. Just, yeah, when evaluating private equity, ruin everything from Red Lobster to, you know, I mean, they've just destroyed businesses, because that's what they do. They create value in and cut, cut dollars. Yeah, it's it's that that growth is hard to, it's hard to manage and hard to do it correctly. So yeah, I understand. So now that we've kind of talked about evaluating vendors, once you actually decide on a vendor, what does a strong relationship with the vendor look like from your perspective? Kelly, I already talked about this. Yeah, I mean, it's, it's that. I think it's that that recognition, if they can recognize that we have aligned interests. And not just as a revenue source. That's when then that's when there's an opportunity to build a relationship. I mean, it doesn't have to be like, hey, we're a relationship, but if they want to see my business But if they want to see my business succeed, then through whatever it is that they're offering. So for example, I've got a really, had a really great printer vendor. Now they had their struggles across the org, but the account manager was great. He was responsive. I had his cell phone number. I could pick up my, I could just call him whenever and he would look into it and he would find answers and he would push back. You know, if I said, oh, we've got a problem, you know, this printer has been terrible. He would be like, well, you know, you've only had it for a year. Let's service it. You know, this is, let's, let's, let's figure this out because it's not just about the customer's always right. I'm, I'm, you know, I got to deal with my internal customers who are sometimes they're not. Right. And, and so when negotiating that I'm okay with, as long as there's a willingness to negotiate back. And so when I say, Hey, this is not optional, we're, we're at the point where my internal customers have to have this copy replaced because there is so much stress and frustration. And you say, you've got another year out of it. I don't care. He's like, yep, let's do it. Your customers are my customers and we can work together. Those are the, those are the places where I've seen the most success in, in relationships. And I don't know if this is true. Like it's a rule of thumb rather than a universal rule, but I've had the most success with people who are local people who share a context and are able to, to say, Hey, you know, I, I might see you on the street. You know, let's meet at your office. Let's have a conversation face to face rather than just a remote discussion. Yeah, that's, that's very important. And for me, it's been, you know, in addition to that relationship and going out and having a beer and talking shop and getting to know the people, you know, like on a personal level, developing those relationships. It's also about like, if it's a pretty large vendor or, you know, they have conferences and things like that, making sure you make that step to go to those things, right. And connect with everybody there. Cause like last year was the first time I went to ITX with Ninja one, which was amazing. It was great to connect with, you know, everybody and see that they're dealing with the same things and they're just as happy about the product that I am, you know, show your face at their events. I mean, I do that with TD Cinex and, you know, Ingram micro and, you know, they put on these massive events all the time too. And it's a good place to connect and you really get to know the vendor, but you also learn like who's the point of contact, who can connect with, you know, and, and like you said, Kelly, they get their cell phone number while you're there, you know, after they've had a couple of drinks. Hey, can you give me your cell phone number? Ah, yeah. So that's, that's, that's a great way to really kind of embed yourself in with this vendor and then to embed with you. And then you develop that relationship and you find out, Hey, you, these are some really good people sometimes, you know, and you find, you know, then you, then that sympathy, empathy creeps in that. Okay. I understand you guys have this price, but you know what, you're responsive, you know, I'm going to, you know, go to battle for, for you, like you were talking about, Kelly. How do you set expectations on day one where, you know, like what expectations do you even set to, to make sure that that relationship starts off on the right foot? Badly, I mean, it's, it's, I've never had a good, a problem-free vendor launch. There's always a mismatch in expectations. You know, so it's, it's iterative. It's kind of, okay, Hey, that didn't work. You know, Hey, your, your support team didn't, didn't meet our expectations. Let's, let's re-center on what, what is normal and let's, let's also help me set my internal folks expectations. Okay. So you say, you know, two business days response time, okay, that that's great, but we need an escalation path if that's not sufficient for the given situation because we rely on your tool and we give you tons of money and it would be a bummer to have to find somebody else that does the same thing, but that's also on the table. And so, you know, I've, I've had some, some really bad vendor launches where the expectations were just totally, totally missed. They assumed their things. We assumed our things, but yeah, it's just a process. Yeah. I don't think that it's, you know, having, having good documentations, I think that DEQ and the Clark shared is, is the beginning of some of those things, of those assumptions. But you know, when, when we say, you know, what is, what is your use of AI, you know, and they'll provide us, especially salespeople, because honestly, they don't know they're, they're just kind of, well, the sales brochure that we got during the, you know, here's, here's the presentation that the technical guys gave us last month. And so I'm just going to pass on the slide deck. They don't know that, that, you know, they're using an AI platform out of China that's stealing all their data. So you just, it's, it's a back and forth. It's, it's a dance. It's, it's, you do your best and then you fix the things that are not working. Yeah, I think the, so yeah, that's a really good point about the, the disconnect between sales and tech, you know, especially when you're dealing with software and services and hardware, you know, every now and then you'll find a really good salesperson who really does go deep in tech. And you know, again, that's, that's the one you want to have beers with and hang out with and get their cell phone number. But I, usually it's a bad sign in the onboarding process that, you know, when you just get that sales sales rep who they did just throw at you, it's a new person because they're moving somebody up or they're laying somebody off. And you know, it's very challenging in the very beginning. So you get an idea for like the organization right away and then you go, you switch to, okay, this sales tech does not know tech very well, but if they go above and beyond and say, Hey, I don't know this, but I'm going to get you in touch with who does and they are a connector within our organization, then that communicates to you that, man, they're going to make it happen. They're not just like doing that Friday afternoon cold call before they dump for the weekend, you know? So, and you know, again, I keep going back to this template that I've built because I've made so many mistakes. I mean, there have been so many mistakes, like you said, Kelly, the expectations that you set up front are the most important and there's often, that's where all the disconnect always is because you're making assumptions of, Hey, this is my standard level of support and service and SLA. And they have a totally different variable that they're working off of. And, you know, if you can just drive that conversation sooner, because man, I've jumped into so many relationships with vendors and things like that before I've even qualified stuff. And I'm like two days, two weeks in, like, Oh my God, how can I get rid of these people? Oh no, it's a three year contract. So I made some stupid decisions when I was younger, but you guys can learn from my mistakes again. Integrations, that's, that's where I've seen the most mismatch in expectations. Yes. You know, I'll be like, okay, do you integrate with this platform? Here's our, here's our point of truth. And oh yeah, we totally can. And then it's like, okay, let's, let's get working on this integration. Okay. So you're going to have to write an SFTP script and you're going to have to upload all this data. You're going to have to clean all these fields. And if it's not this exact format, it's not going to work. And we get it in that format. And they're like, oh yeah, but actually, oh, so frustrating. Yeah. Do you ever talk to like sales engineers and stuff? The, you know, the folks that have a little bit more technical know-how during that evaluation process to see if they can explain to you how the things work before you jump in? Yeah. Yes. It's not, if, if we're going to do it, the level of integration of any kind, it has to have some other technical people involved in the sales process. Yeah. That said, you know, the, it's always in the, the more involuntary vendor relationships that, that things get sideways where, you know, we've already decided on this vendor or these two vendors. We're, we're, we're moving forward with a solution to our problem. We didn't talk to IT and now you've got to make it work. And those, those are the places where I get squirrely the most because there's, there's not that opportunity to, to say at the very upfront, hey, when you do an integration, what do you need? What are your expectations? What is the process of getting that data out of our tool and into your tool? Yeah. How do you try to avoid those kinds of issues with people just signing on vendors without checking with IT? Is there a way to kind of circumvent that issue? Is it working with finance to make sure that that is part of the procurement process or what does that, what might that look like for an organization? I've, most of the organizations that I've worked in, IT has been weak in terms of authority to set those expectations. And, you know, I put in place a policy, got it approved by the CEO and, and it still got ignored because there was no, there was no teeth behind it from the CEO to say, hey, we have a policy and you just violated it. It was a, well, just this one time, times 40, you know, yeah. And it just kept going and going and going. And so that, it takes a culture. It really does. It takes a tight relationship between finance leadership and IT to be successful in those areas and the willingness from the leadership of the organization to either invest IT with the authority to say, you didn't work with us, we're done. Come back to me when you're ready to work with us, or to say, hey, you're done. Have the leadership say, you're done. You needed to work with IT. You know, we're terminating this contract or whatever that looks like. So, yeah, I, I think we've all been dealing with this a lot more and more recently with AI, chat2BT, everybody coming up with their own solutions. And, you know, single hand, I think I've shared a lot of this on other live streams and, and vented and, and, you know, chat and things like that about Claude and people just like, oh, we just signed up for Claude and, and we got the enterprise and we're going to bring this in the organization. Well, the best way, I think we've talked about this several times too, is education, you know, educating those CEOs and people like that who make these decisions and go, okay, stop. Do you know Claude was compromised three times in the month of March, including exfiltration of data, including their, their source code was published for like a couple of hours, which leads to more cybersecurity risk in the future. So when you start tackling it from that perspective and, you know, because a lot of people don't think about this stuff, they're not in IT. And when you start doing this over and over and over again, it puts in their mind, hey, I got to remember to include IT anytime we make these decisions. Because, you know, sometimes it's, I don't look at it as malicious. Sometimes it's just a CEO, you know, wanting to make something work and make it happen. And somebody from sales says, hey, we've got to have this tool. And he's going, yeah, okay, let's make it happen. And then they take it and run with it. And they forget that there's a whole other aspect of this, which is the IT, like who's going to bring this in. And the other thing is, hit them in the pocketbook, right? And like we've showed before, get an Excel spreadsheet out, show them how much this is really going to cost them as far as securing it, as far as creating policies around it. And, you know, you don't just dump this out in the open wild and expect it to, you know, play nicely with the organization. So always put that stop, you know, when they bring it to you and say, well, wait a minute, why wasn't I consulted? Because. Because of the, and I'm gonna come back with my research and just take, you know, do a couple of hours of diligence. And typically you can find really good reasons why it needs to be vetted. And once they, you keep doing that a couple of times, then you're definitely gonna be a part of that conversation in the future. Yeah. Now, some of it is malicious, I will definitely say. Kelly is like, there's, I'm just gonna do it. Like, you know, CEO or, you know, CEO level kind of person just like, nope, we're gonna do this. And makes a arbitrary decision and we'll figure out the details later. But maybe you don't need to be working for that organization. Trade shows, I hate trade shows because people always come back with it like, oh man, I spent this 20 minutes with this guy and he told me that AI is gonna solve every problem we've ever had. It's gonna make us billions of dollars. Yes, painful. Yeah, yeah. What's interesting is like, so we're very niche. We're focused on private equity. And you can tell when these guys come back from their trade shows, they all have the same requests. Like this year, it's everybody the same month. We need Claude in our organization. We need OpenClaude, we need a Snowflake server, you know, all this stuff. I mean, they get it and you go, well, wait a minute, so-and-so just said this. You guys got a template you're working off of? Or, you know, it's definitely a trade show or something industry specific about, you know, what's new on the horizon, you know, WEF kind of stuff, you know, that's coming down the pike. I mean, that's horrible. I agree with 100% there, Kelly. I mean, you can, it's like clockwork. You know, they come back, oh, this solution is gonna solve everything. And then you get three months into deployment, oh, it's not really doing what they said it was, is it? Yeah. Worse, it's tenfold now with AI because you got all these people doing these videos. Oh, you can create a website in five minutes for your organization. Yeah. No, you can't. I don't know if y'all saw the, there was a, yeah, Claude powered AI coding agent deletes entire company database in nine seconds. I was, yeah, I was astonished. And there was a lot of things that went wrong. The fact that the cloud vendor put the same, the backups on the same volume as the like source data. It's like, oh, there's a lot of issues happening, but, you know, you don't want your AI agent to admit that they knew it was wrong, what they were doing and then just go through it anyway. Yeah, yeah, it's- More things change, more they stay the same. Yeah, yeah, exactly. So we talked a little bit about vendors and how they communicate with you, not just during the sales process, but after you are sold to, and you are now a customer, what are some green flags when it comes to vendor communication? We've talked a lot about red flags, but I would love to know what y'all think is, you know, really positive in that communication process. Follow up. You know, the best reps are the ones who are contacting me a month later going, how are things? Because I'm not part of their pipeline anymore, unless they're focused on a long-term relationship. And so if they don't care, if I'm just a revenue source, they're not gonna follow up unless I'm threatening to leave. And so the green flags are the reps who are, you know, especially if they see that we're not utilizing the platform fully, and they're coming back and they're saying, hey, you know, can I loop in some other folks to make this, to help you be more successful? Who can I involve to make sure that you're using our platform well? Those are the ones that are the, those are huge green flags. Along with the beers and the cell phone, actually. Yeah, that helps a lot. Yeah, for sure. Yeah, that's a really good point that Kelly brings up is like, yeah, you know, I've had situations where, you know, the sales rep is like, okay, they're done with their deal. They've moved on, but they call back like six months later, hey, how's it going? That's when you know you're, you know, you've got some really good, whether it's a really good organization, or, you know, just a really good person, and you latch onto that person, you connect with them on LinkedIn, you follow them, you get their digits, and anytime they jump and go to another vendor, you follow them as well, and they'll take that same work ethic wherever they go. And it's always kind of nice to kind of follow those people. I actually have some vendors that I follow around from vendor to vendor to vendor. And not that I've used them every single time, but when they actually land on a vendor that I'm actually interested in, I'm like, okay, why did you make this choice? Why are you there? You know, I have a lot of respect for you. Let's have a conversation. Yeah, what makes you willing to advocate internally for a vendor? You know, outside of cost, if are there any of those green flags that you would kind of weight more heavily and make you more willing to advocate for potentially a higher cost? Well, so internally for me, it's, hey, is this okay? Yeah, it's good. But for clients, like Kelly would probably be able to answer this a little bit better from an internal perspective, but we kind of the same way with our clients, right? Because the clients come to us if they don't already purchase it. If they come to us and ask us, then, you know, that's a good opportunity for us to validate that product, you know, and go through that process with them. But how we advocate is, you know, typically if we already have another relationship with another client, then we're gonna advocate for that client. This is their solution compared to what you're bringing with us. We've had this relationship for, you know, 10, 15 years, and we are confident that they, you know, we are confident in our relationship with them that they're gonna deliver what you need. This is a new vendor we haven't worked with, you haven't worked with. Let's explore it and let's compare, but let's bring in, you know, those other relationships as well. So, and it's not always about money. It really, you know, like Kelly said earlier, it's really about who's gonna make it happen for you at the end of the day, because if you're just looking at money, then what you're missing is the admin time it takes for those cheaper organizations, that the strain of the admin time on your staff, on your admin staff, on invoicing, on it just domino effects all the way to, you know, from support to invoicing to, you know, getting things done with that organization. It's, man, some of them are just all chat nowadays. They want everything to be done through chat. And that's just, that's painful. And that's because you're on an AI chat and they're trying to solve their problems through AI first, but that just becomes so annoying. So I'm not gonna advocate for those kinds of people. So, thanks. You know, outside of the things we've already talked about, you know, I'll advocate for a mediocre vendor if they're extending the stack. Because, yeah, Clark, just what you brought up about the footprint, the admin time, you know, I'm advocating for my team's time by saying, okay, let's centralize. We have SSO, we have integrations, we have all this stuff. They're not the best, but we know them and we're done. So let's use this other tool that they're offering us instead of another third party, because we don't have to do all that upfront work to get them going. And yes, the other one is fancier, shinier, more deeply embedded in AI, which, you know, that's the sales pitch, but that's not the reality that's good. But, you know, we've already gone through all the vetting processes. We know they're compliant with all of our standards that we have to hit. You know, this is time savings, which is cost savings. And they're mediocre, but we're done. And we can go from zero to 60 a whole lot faster than we could with this third party. So that's the other part in addition to the relationship. Yeah, absolutely. Agree with that a hundred percent. Awesome. Well, we're right. We're approaching time. So I want to make sure everybody gets either to their next meeting or gets to lunch or whatever they got going on. But I really appreciate y'all being on for this stream. I think this was a lot of really good information and I'll make sure that there is a wrap up posted and everything with all the key takeaways from this. So really appreciate y'all being on as always. I'm very disappointed you didn't bring in the most important person in the room, which is your dog. Oh, she was in the room. And then. You're going back to her and I'm like. Got a little bit. She wanted to go outside. And then my husband, he works very late. So he came out of the bedroom and she was, she was freaking out a little bit trying to get out of the office. So I. Is that how you pronounce it? Get her out, get out and do her thing. So. But actually on that note, if anybody has any pets that they want to share. Oh yeah, please do. There is, there is a thread with all of the, with all of these IT pets. And yeah, I would love to see everybody's, everybody's animals. I know I love sharing pictures of my animals. So definitely, definitely feel free to jump in. Um, yeah, so we have a stream coming up in a couple of weeks. That one is actually about empowering diverse IT talent. I think it's gonna be a really awesome discussion. I think Clark, you're on that one as well. And yeah, I think it's gonna be a really good discussion on how we can kind of focus on improving diversity in IT. It's always nice to have different voices from all different experiences. And a way that we can work on that is by improving diversity within IT itself. So yeah, gonna have some folks on to discuss that. And I think it'll be a really good conversation. So we'll be back in a couple of weeks on May 12th. And for now, we will catch y'all later. And hey, look, it looks like the storm finally, but it hit Clark just in time for him to log off. My phone is on the flutter right now, so. Yeah, well. Thanks Clark for having me guys. Yeah, thank y'all. It was a good time, thanks. Thanks for everything you've done. Stay safe Clark. All right, take care y'all.

TL;DR

  • Implement a comprehensive due diligence questionnaire (DDQ) covering compliance, cybersecurity, AI policies, and ownership structure before engaging any vendor—a vendor's willingness to complete it thoroughly is itself a critical evaluation signal.
  • Private equity ownership is a major red flag that often leads to product integration problems, account management churn, and service degradation as growth-focused acquisitions prioritize consolidation over customer experience.
  • Strong vendor relationships require going beyond transactions to build genuine partnerships through face-to-face meetings, attending vendor conferences, and maintaining direct contact with responsive account managers who understand aligned interests.
  • Account representative turnover has become endemic in the industry, with some IT leaders experiencing five different reps in three years—making it essential to identify loyal salespeople and follow them across their career moves.
  • When evaluating vendors, consider the total cost of ownership including administrative burden, support quality, and integration capabilities—sometimes a 'mediocre' vendor that extends your existing stack delivers better value than a feature-rich standalone solution.
  • Vendor launches rarely meet initial expectations, requiring iterative adjustment and clear escalation paths beyond standard SLAs to ensure critical issues receive appropriate attention when standard response times are insufficient.

Vendor Evaluation and Due Diligence

The discussion opens with Clark Sandlin, CEO of Zerca (a managed IT service provider), sharing his evolved approach to vendor evaluation over 35 years in IT. He emphasizes the importance of a formalized third-party due diligence questionnaire (DDQ) that covers compliance requirements, cybersecurity policies, backup procedures, and AI usage. This comprehensive document, originally developed for SEC compliance with registered investment advisors and private equity clients, has become central to Zerca's vendor engagement process. Clark stresses that a vendor's willingness to complete the DDQ thoroughly is itself a critical signal of their professionalism and transparency. The conversation highlights sourcing vendors through peer networks, with the IT Leadership Lab community serving as a valuable resource for recommendations from practitioners who balance technical expertise with management responsibilities.

Building and Maintaining Vendor Relationships

Both panelists emphasize that strong vendor relationships extend beyond transactional interactions to genuine partnerships built on aligned interests. Kelly describes the ideal vendor relationship as one where account managers are responsive, have direct contact information, and are willing to negotiate honestly rather than defaulting to 'the customer is always right.' The discussion reveals that local vendors who share context and can meet face-to-face often provide the most successful relationships. Clark advocates for attending vendor conferences and events as a strategic way to build deeper connections, get direct access to decision-makers, and understand the vendor's culture. The conversation acknowledges a significant industry challenge: high turnover among account representatives, with some participants experiencing five different reps in three years. This churn, driven by both layoffs and sales industry dynamics, makes it crucial to identify and maintain relationships with individual salespeople who demonstrate loyalty and technical depth.

Red Flags and Strategic Considerations

A critical insight emerges around private equity ownership as a major red flag. Clark explicitly states his policy of walking away from PE-backed vendors, citing how growth-focused acquisitions lead to product integration problems, departmental silos, and account management instability. He contrasts this with NinjaOne's approach, praising their independence from PE ownership. The panelists discuss how vendor launches rarely go smoothly, with mismatched expectations being the norm rather than the exception. They emphasize the importance of establishing escalation paths beyond standard SLA response times and the hidden costs of 'cheaper' vendors that create administrative burden through poor support channels like AI-only chat systems. Kelly introduces the concept of advocating for 'mediocre' vendors when they extend existing technology stacks, arguing that integration benefits, SSO capabilities, and reduced onboarding time can outweigh the appeal of feature-rich but standalone alternatives.

Practical Vendor Management Tactics

The conversation provides tactical advice for IT leaders managing vendor relationships. Clark recommends following exceptional salespeople across their career moves, maintaining relationships even when not immediately using their current vendor's products. Both panelists stress the importance of periodic vendor reviews—annually at minimum, quarterly for critical relationships—to ensure ongoing alignment. They discuss the value of transparency in vendor communications, including asking direct questions about AI policies, data sovereignty, and ownership structures. The discussion acknowledges that sales teams often lack deep technical knowledge, making it essential to connect with technical resources during evaluation and onboarding. Kelly emphasizes that cost should never be the sole decision factor, as the true expense includes administrative overhead, support quality, and team productivity impacts. The session concludes with recognition that vendor management is an iterative process requiring continuous adjustment of expectations and ongoing relationship maintenance.

Chapters

0:00 - Introduction and Community Overview
1:11 - Clark's Background and Business
3:18 - Vendor Evaluation Process and DDQ
7:03 - Due Diligence Questionnaire Deep Dive
24:34 - Account Representative Turnover Challenges
28:38 - Building Strong Vendor Relationships
33:26 - Setting Expectations and Onboarding
49:03 - Following Salespeople Across Vendors
49:56 - Advocating for Vendors Internally
54:00 - Closing and Next Stream Preview

Key Quotes

3:38 "We have a DDQ that we use. It's a third party due diligence questionnaire. And we've developed this over maybe the past 10, 12 years. And each year we kind of add more to it."
26:39 "If it's owned by a PE group, walk away. Like, that's I asked Ninja one this at the ITX last year, I was like, Are you guys bringing in PE because that always ruins everything? ..."
28:11 "Private equity, ruin everything from Red Lobster to, you know, I mean, they've just destroyed businesses, because that's what they do. They create value in and cut, cut dollars."
30:43 "When I say, Hey, this is not optional, we're, we're at the point where my internal customers have to have this copy replaced because there is so much stress and frustration. And you say, you've got another year out of it. I don't care. He's like, yep, let's do it. Your customers are my customers and we can work together."
49:19 "Anytime they jump and go to another vendor, you follow them as well, and they'll take that same work ethic wherever they go. And it's always kind of NICE to kind of follow those people. I actually have some vendors that I follow around from vendor to vendor to vendor."
51:28 "It's not always about money. It really, you know, like Kelly said earlier, it's really about who's gonna make it happen for you at the end of the day, because if you're just looking at money, then what you're missing is the admin time it takes for those cheaper organizations."

FAQ

How do you handle the constant turnover of vendor account representatives?

Build relationships with individual salespeople rather than just the vendor organization. Exchange cell numbers with exceptional reps, connect on LinkedIn, and follow them across their career moves. When you find someone loyal to their organization who demonstrates technical depth and responsiveness, maintain that relationship even as they change companies. This personal network becomes more valuable than any single vendor relationship.

When should you advocate for a more expensive vendor over a cheaper alternative?

Consider the total cost of ownership beyond the price tag. A responsive vendor with good integration capabilities, established SSO, and proven support can save significant administrative time and reduce team frustration. Sometimes a 'mediocre' vendor that extends your existing technology stack delivers better value than a feature-rich standalone solution that requires extensive onboarding, creates another security review, and adds administrative overhead. The cheaper option often costs more when you factor in support quality and staff productivity.

What are the most important questions to ask during vendor evaluation?

Use a comprehensive due diligence questionnaire covering compliance requirements, cybersecurity policies, backup procedures, AI usage policies, and ownership structure. Specifically ask if the vendor is owned by private equity, as PE ownership often signals future problems with product integration and account management stability. Inquire about their local presence, escalation paths beyond standard SLAs, and their willingness to provide direct access to technical resources beyond the sales team.


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