Doug Miller at Brightworks Shares on How Sales Coaching Builds WINNING MSP sales teams.

Hi, good afternoon, everybody. My name is Carrie Richardson, and I am the host of WIN, What's Important Now. With me today is Doug Miller from Brightworks. Doug, thank you for joining me today. How are you doing?

Great. Great. Thanks for having me on.

Brightworks has been working with Fox and Crow for a couple of years now.

Yeah. We started in 2025,

So let's talk a little bit about what life looked like before you started using, Fox and Crow and the MSP sales process. tell me about your business and the things that you tried in sales

sure. So we're, we're almost 15 years old now, and, honestly, we've spent just huge amounts of money over those 15 years trying to crack the MSP sales problem. selling for MSPs difficult. There are a lot of MSPs out there. and buyer is not especially well-educated about how to tell the difference between MSPs, how to understand what makes a good MSP versus one that's gonna be a problem for them. And so differentiation becomes a really big deal. But even more than that, there's just so much competition, it's, it's difficult to sell. to begin with, like a lot of MSPs, were doing owner-led sales. I did a lot of sales. I had done a lot of selling in my career. even though I'm an engineer, I'd also done a lot of selling. So we started that way, but it became very obvious to me early on that that wasn't a good long-term solution, right? There was no way I could really grow the business if I was buried in the middle of it. But I did a lot of stuff. Even then to try build a sales process, enrolled in LinkedIn programs. remember I... One program, yeah, got me, tons of LinkedIn contacts, but they were pointless, right? weren't people that were buyers. It was a, "Well, network with these people and they'll lead you to buyers." Well, they might lead me to another person on LinkedIn, and then another person on LinkedIn. And yeah, I was having a lot of meetings, but I wasn't closing a lot of business, right? we did a lot of cold emails, through marketing companies, and everyone had their own spin on it. We finally ran into one that, had been highly recommended to us, and we told them what we were gonna do, and they were like, "Yeah, don't do this. It's pointless for you to do this in your industry. There's too many people doing it, and you can never get anything." we never did. at one point, I think were sending about 90,000 cold emails a month, and we never generated one single lead. Not one. So that was pointless. we were hiring salespeople then. We started hiring different salespeople. actually hiring a true MSP salesperson is tough. There are a lot of people who sell technology and have sold technology, but to find somebody who's actually an MSP salesperson, given that most MSPs are small and most MSPs have owner-led sales, finding an MSP salesperson is tough. so you hire people from other industries. They don't know your industry, so they have to be educated on that, but then they also don't know how to sell this. So we had a lot of salespeople who just weren't getting any good results. The level of prospecting that they needed to do was something more than they were prepared to do, and they didn't really know how to do it. So it didn't work. We've spent multiple hundreds of thousands of dollars over the course of the 15 years trying to build a sales process, whether that was me, whether that was salespeople. at one point I had salespeople and, people that were, account development people that were trying to work the phones create leads and that didn't work. So really were to a point a few years ago we were growing the business well, but it was all through referral. It wasn't through any successful outbound program at all.

What are the big problems in your mind when it comes to having a business that's solely built on referrals?

well, the first problem is that referrals are all relationship driven. And if the relationship again is with the owner, which is often the case in MSPs, then when the owner tries to exit the business, there's no business there. it can't grow, right? So that makes it a lot less attractive from sales per- selling the business perspective to an investor, right? haven't created a business. You've created a job, and you can't ever get out of it. having tried to acquire some other MSPs, we found that again and again and again that, yeah, it was owner-led sales. It was all referral. All the existing customers were relationships with that owner. Any new prospects were gonna be referrals to that owner. So what would we really be buying? they weren't gonna hang around, and we weren't gonna get new business out of it. So why bother? It didn't make any sense. this is my retirement. This is a thing that I've spent, almost two decades building. I need to get cash out of it when I decide to exit. So cannot have something where a critical function like sales is tied to me and my personality.

As lovely as that personality is.

Well, there you go. And that's the problem, right? If, better you are at this the more that you, not to pat myself on the back, but, if you are an engaging person, that's great, but that lowers the value. that might get you sales now, but it means you don't have a business.

So what prevented you from being able to teach someone else how to execute on the sales playbook that you were managing

a really good question, and I think it's a question that a lot of MSP owners run into, is a lack of understanding that you, as the owner, have tools that nobody else can have, right? you make a promise as the owner of the business, that's seen completely differently than if a salesperson makes that promise, right? So you can't depend on that. You can't turn to the salespeople and just say, "Well, say this," because it won't be seen the same way. I'm an engineer. I'm a technical person. Again, that's often the case with MSP owners. They, know the business, they know the technology, and so they're able to talk in a manner to prospects that, again, a salesperson who isn't probably a technical person can't really do, So we'd hire salespeople, they're great people, but can't generate the level of trust that the owner can right off the bat, both because they're not the owner and because they can't look at technical problem and say, "Well, if I were your MSP, this is how I would solve that." Right? They have to present a packaged solution- That they don't know enough from a technical perspective to be able to go, "Well, this is what we would do in this specific case." They're good at presenting that package solution, but people are looking for more. This is a trust relationship, and so has to be developed, and salesperson can't do that the same way that an owner can.

So what was the biggest transition year one for you working with a niche specific sales coaching organization like Fox and Crow?

The first thing that we really had to get our head around be willing to do was accept that this was gonna take a while This wasn't something that we were gonna come into and 60 or 90 days into it, everything was gonna be just hitting on all cylinders. It was gonna be producing, all the revenue that we expected, it takes some time both to coach the team into understanding how to do it, and then generating enough activity for that activity to start to pay off. So you can't go, "Well, boy, I've, waited this long and I'm now financially in trouble. I need new business within 30 days," and expect that you're gonna dive into a program like what Fox and Crow does and see that happen. Just there's not enough time

So year one was a slow build?

Yeah, though it, as I say all that, it was quicker than we thought. it was a slow build, but we started getting results. we got our first appointments even closed business within about 120 days. It wasn't something where we could point at it and go, "Okay, this is, this is gonna happen every month," right? But it was happening. We could see the results. We could see that, an increase in activity. If you go to sales coaching, and I've been to a ton of it in my life. you're told, "Well, cold calling doesn't work. Don't cold call. have to do relationship selling, you have to, work social media, you have to work LinkedIn, you have to do networking." and while all that is true for certain kinds of business, the bottom line is cold calling works if you put sufficient activity into it, right?

You don't have to tell me twice.

It just does. And, there's a lot of coaching out there today that will tell you that's not true, that cold calling is dead. let me say that isn't true, and I think it's particularly true for our industry. one of the things about being in our industry, about being an MSP is nine times out of 10, a new prospect will come because you connected with them at exactly the right time. And exactly the right time means when they are upset at their existing MSP. Something's happened- The existing MSP has not delivered, or they don't have an MSP and they had a phishing attack or something like that. you're not gonna get that by sitting around and waiting. You have to be regularly reaching out to a lot of people to find the people who have had that event where they're ready to talk. Otherwise, I've joked for years that this industry is like selling prepaid funeral plans. Nobody wants to talk to you about it until there's a body. When there's a dead body, everybody's ready to talk about funeral plans, but same thing here. Until there's a problem, no business owner wants to talk about IT being an MSP. That body could be a lot of things, but you have to go out and hunt for it. They aren't sitting there going, "Well, who can I call?"

Well, the, we're not gonna talk about creating more bodies so that we can- close more of those deals. Right. But there is an interesting parallel, like when you buy a funeral the day that you need it, one, not only are you operating on the most stressful day or one of the worst days of your life, you're not thinking about anything other than this horrific tragedy that has befallen your family. That's right. And all of a sudden, like you get the bill afterwards, and you were kind of in a blur when you bought it, and like, "Holy shit, I didn't realize I'd spent $60,000." Oh, yeah. Oh, yeah. And funeral home isn't incentivized to tell you to spend less, and you're operating from this place of emotion. The most expensive time to buy IT support is when you need IT support we use that prospecting all the time. You know what? My boss is not gonna take your call at 3:00 in the morning when you're having an emergency if you guys have never spoken before, so you're happy with your current provider, but, what happens when one day you're not?

Yeah, and we use that all the time, right? And, it's successful because- Business owners, particularly small business owners, like I said, they don't wanna talk about this, they don't wanna think about this. there is perception in the industry that switching IT providers is enormously painful. They're not wrong. can be. but given that, right? The wrong time to make that decision is when you already have a problem, right? we've found that, we have customers where- they switched to a new IT provider because of problem with the prior IT provider. They're 90 days in with the new provider, and we're talking to them and they're saying, "We made a huge mistake. This guy's worse than the one before How do we get out of this? what are we gonna do? And so, would be great if the people who buy our services could get a little bit better educated on some of these things, but the fact of the matter is it just isn't that way. So you have to be reaching out, you have to be building relationships, you have to have an outbound program to touch as many of those people as you can, and to do it frequently enough that when- I

think you were very fortunate that your team, your team kinda wholeheartedly embraced-

Yeah

process, and not everyone does. Like, we do lose- people at the beginning, of a Fox and Crow engagement when people find out how much their job may be changing in the next 120 days.

Right. Yeah, that's absolutely the case, right? let's face it, a lot, a lot of people aren't really interested in making 100 phone calls a day, 90 of which nobody answers or they hang up on you. You have to get the right person. And then as leadership team and as an organization, you have to be prepared to support that person, right? You have to recognize that what they're doing is tough, and if all you're ever doing is going, "Come on, come on, you gotta get something closed," as opposed to recognizing that, what? It, they need a day off, they need some time here, they need a commission structure that's gonna make this really worth their time. They need us engaged both with them and with Fox and Crow, not just going, yeah, go do the thing and come back to me when you've landed some activity," right? And I think that's the failure of a lot of leaders and a lot of management teams and a lot of owners, is they think, "Well, put you in coaching. Why aren't you delivering?" "If you don't deliver by next week, I'm gonna get rid of you."

Hmm.

And-

That's a stressful environment to work in.

Right. I mean, who would wanna be in that? So no wonder when you turn around and go, "Oh, by the way, you need to make 500 calls a week, and I'm watching that, and if you don't do that- And you don't land something within 90 days, your job's in jeopardy. Now, I'm not saying that go for two years, right? If you've got somebody that just... and we let some people go after we'd been doing this for about six months, where, we could just see that hit the wall. number of calls, amount of activity dropped off, and they just weren't doing it anymore. They, and they, no amount of coaching got it back. It wasn't a thing for them to do, right? it might have been, they might have been successful in a different industry But again, this industry's very difficult. You're gonna have to talk to a lot of people

So would it surprise you to know that currently the, your sales rep was one of the highest performing reps that we coached here at Fox and Crow?

doesn't really surprise me, because, first of all, he's been committed, right? He's all in. and he's been very coachable, right? He listens to the coaching. He tries to perform what's on the coaching plan. finally found, after 14 years, a sales rep who didn't take the attitude of, "Well, I know better than the coach, so I'm just gonna do my thing." what's unusual about that is our guy's very experienced. He's been selling for 20-some years. he's not kid. but rather cop an attitude, he was like, "Hey, this is a new industry. This doesn't work the way everything I've done before works. I need help." And he was willing to listen. at the same time, we've been very supportive of that, right? We've continually invested in the coaching. We've invested in, intensive sessions, as well as peer coaching. We've invested in the, the CRM system and the, learning management system. So he's got all the right tools. he and I meet weekly in addition to the coaching, in addition to, everything he does with Fox and Crow. He and I talk regularly. we converse during the week when different things come up. So you have to stay engaged. can't just go, "Right, like, go sell and tell me when closed something." the organization as a whole has to be committed to this. This isn't just something where you're saying, "Yeah, I'm gonna put my sales rep into this program magic is gonna happen, but we're not gonna change anything with the rest of the company."

What's changed for you over the last couple of years?

well, it's all been very good, right? I mean, the, biggest thing is I'm not involved in the sales process anymore. we're closing business, we're bringing customers in that I've never spoken to, and they don't have a relationship with me I think to a lot of MSP owners, that would sound very threatening. That would be a scary thing. to me, it's a great thing because it means that we're not harnessed to me anymore. We're not shackled to me anymore. And so I can go do what I wanna do, right? I'm at the point where I've got four grandchildren, my wife and I like to travel. We're getting ready to go to France in about two and a half weeks, and I don't have to worry that sales is gonna stop while I'm doing those things. it's going on. Business gets closed. I can remember when we were in France, the last time, a lot of business gets closed. In fact, my team jokes that, "Hey, we need to send Doug on vacation again because when we do, we close business." they're not wrong, right? luck of the draw, but they're not wrong. I've had to- Get okay with the idea to not intervene in the sales process, to not stick my oar in and try and tell my sales team, "Oh, you gotta do this, or respond this way. Work with your coaching. Use what Fox and Crow is telling us. Lean on the CRM. Lean on what we've learned." Use their process Because that's what's gonna work, not what I used to do. At the same time, it's been important for me because we have, right? We've sold by referral, we've got lots of other people in our organization who also have developed a lot of relationships with customers, which is great. But the same thing then happens there, right? a referral comes in from an existing customer, it doesn't go to the sales rep, it goes to my director of engineering or my COO or somebody like that because they have a relationship with an existing customer. So they turn around and they follow up on the referral. Well- That's great, but it's just replicating the same problem, right? So we've had to get them to back out of wanting to be on every sales interaction so that they can do what they're supposed to do, and the sales team can do what it is supposed to do. And once we got that sorted out, we started getting even better results.

Yeah, you had mentioned, numbers-wise that you were on target to, have a pretty significant year.

We are. last year was our best year ever by, oh, about 50%. this year will be better than last year. we are consistently profitable. We consistently bring in new business every month. not all of that's generated by our outbound program, right? You're still gonna get the referrals and things like that. But even that, has benefited immensely because order to do the outbound thing correctly- And to have a sales team that can truly sell, you have to get your packaging and pricing really squared away. You have to know who your ideal customer profile is, right? have to get all those things lined up, and, because the sales team won't know what to do if you don't have that. Once you have those things in place, then if you get a referral, again, you have the packaging, you have the pricing that makes that go faster. And most importantly, we really dealt with this early this year, is knowing who our customer is and who we're selling to so that we don't take customers that aren't good fits. However that comes in, whether it comes in through prospecting or referral, to look at a customer and go, "Okay, you know what? I'm sure we could land these guys, but if we did, that might be the worst thing that we did."

What are the red flags for you that indicates that you don't want this client?

the first one is that they have a significant amount of technical debt and aren't willing to address that, right? You've got servers running Windows 2018, and, you got a bunch of old stuff. You're gonna have to fix that. you have security issues. You're gonna have to fix that, and we're gonna quote that stuff to you in the sales process. We're gonna build a plan for you, and you need to agree up front that we're gonna do these things. Because if they don't, then what they're doing is they're going to rely on it. They're gonna just let it break and turn around and go, "Well, you're the MSP, go fix it." And the hours never be profitable dealing with that, right? Will just never be profitable. that's a big one. There are verticals that we specialize in, and being clear as to what those are, and verticals that we don't wanna touch. There are certain things we don't do. We don't do, for example, we don't really, we don't do any government business. are not big on the government procurement process. We don't have the people internally who are skilled in responding to RFPs that stuff. So we don't do education, we don't do government. ironically my COO comes out 17 years the public sector. So he's got the background part of why he came to me was because he didn't wanna do that anymore. so look at those kinds of things, right? we, just don't wanna engage where we're not strong. We found that twisting our company around in order to meet the needs of somebody who doesn't fit our profile never works out and never makes us money.

So what's next? You had, your best year ever last year, and this year is shaping up to be better than that. What's the exit plan?

The exit plan is here within probably about two years, maybe less. my son who runs our technical team and my COO are actually gonna buy the business from me, and we've already made those plans. we've already set a lot of that in motion. there's a valuation that I'm interested in because need that to fund my retirement, and we're basically there. We're very close to it. and, we hit that valuation, and it's really just a matter then of when they're ready so it'll be an internal sale, preserve the culture. not that interested in selling to a PE firm a roll-up or doing any of that. There's a lot of that out there in the industry, and a lot of MSP owners are interested in that, and that's cool. I'm just fortunate that I have people internally to sell to.

So one burden you've taken off of, the buyers now is that sales process.

Correct. Yeah.

Is there anything else that has to get cleaned up before you're gonna be ready to ride off into the sunset?

really for us, not a lot, because spent a lot of years being prepared for that, Again, I can say this because we talked to a lot of MSPs that we thought we might acquire, a lot of MSPs have- don't have clean accounting. They really don't. they've been, keeping receipts in shoe boxes. They've been... There's always a tendency with any small business for an owner to run a lot expenses through that business, and that makes it... I've seen buildings, I've seen guys' cars, I've seen incredible things that are run through the business, we've got a very good, fractional CFO and an accountant that has been with us now for over a decade. The books are very clean. everything according to GAAP, and we can produce a financial statement in a matter of minutes that is accurate. Again, a lot of small businesses, and particularly a lot of MSPs can't do that. That's something that you've gotta get in line. customers get-

What do you think life might have looked like if you'd done something about sales five years ago? Would you be retired now? Would the business be larger? What's your best

guess? Oh, The business would unquestionably be larger. as to whether I'd be retired or not, I'm not sure. if I was, it'd be because I sold it, not to the family, right? there's an issue. My son's worked with- for us now for about 13 years, but, got married, he had to buy his first house and his second house. He's had two kids. Financially, he just wouldn't have been in a position five years ago to look doing this. he's getting there now, right? So I'd have probably have had to sell it to somebody else at that point, and I might have been able to exit five years ago had we done something about sales earlier. I think there's no question I'd have more hair. because five years ago, trying to figure out what we were doing for sales my number one stressor. really has been for about the last five or six years. just what are we gonna do about this? Everything else is running great. Service delivery is great. We have great staff. Everything's perfect except for that. just kept looking and couldn't find an answer for it until what we did a couple of years ago that's made all the difference.

Well, we were, happy to be part of that. We appreciate your partnership. What's the ideal time for an MSP? When is an MSP ready to look at an engagement with a company like Fox and Crow?

Yeah. think that, obviously in your first couple of years, particularly if you're starting the way I started, right? I literally just went to the bank with 500 bucks and went, "Hey, I'm in business." a different story if you have investors or something like that, but if you're doing it the way I did it, that first couple of years, you're gonna be closing tickets, you're gonna be selling, you're gonna be doing all that stuff. But- Sooner is better than later Waiting until you're 13 years into it, 12 years into it, that's playing on hard mode. You'll have spent a lot of years beating your head against the wall, which I did. you've gotta have the income to be able to pay for the coaching. You've gotta understand the industry well enough and what your place is in that industry. So y- you've had to start thinking about your packaging and pricing. You need to think about, who your ideal customers are, who you wanna work with. if you're still in the point of, "Look, I'll take anybody that'll throw me a buck", yeah, you're probably too early, right? But to get out of that, at the same time, have to start thinking about, all right, what is my transition? How do I get to the point? if you as the owner, if your thought process is, "I'm doing this because I like to mess with computers, and I can't see a future where I'm not doing that", you're too early, and you're not building a business When you're at the point as an owner that you're thinking, "I wanna work on the business and not in the business. I don't wanna be a technician. I don't wanna be an engineer. I truly wanna grow a business," that's also the point you need to start talking to people like Fox and Crow and there are other experts as well, right? Like I said, we've had a phenomenal fractional CFO. we work with PEO on the employment and HR side. We've got a great marketing company. I get that all those things cost money, but if I were good at those things, I would be doing those things instead of running an MSP

I think it's a great place to cut. And Doug, thank you as always for your time. Appreciate having you here today. You've been a great partner to us as well, so thank you.

Well, it's been a pleasure to work with you guys, I enjoy talking with you every time we get together. So thanks for having me on.