Marketing Insights From An Experienced CMO

Marketing Insights From An Experienced CMO

Tim Fitzpatrick
Welcome to the Rialto Marketing podcast. Today's episode is a revenue acceleration series interview where we talk to seven-figure B2B business owners and their growth-focused executives who are actively trying to grow their business and get to the next level. We talk about the good, the bad, and the ugly so you can learn from their experience. I am Tim Fitzpatrick with Rialto Marketing, where we believe marketing shouldn't be difficult. Thank you so much for It's been the time to tune in. I am super excited to have Crystal Conkle with me today from The 20 MSP. Crystal, welcome, and thanks for being here.

Crystal Conkle
Thank you, Tim. Excited to be here.

Tim Fitzpatrick
Yeah, I always love connecting with other marketers. I know we're going to have a great conversation. Before we jump into the heart of things, I want to ask you a few rapid fire questions if you're ready to jump in with both feet.

Crystal Conkle
Perfect.

Tim Fitzpatrick
Okay. So very quickly, what do you do? How long have you been doing it?

Crystal Conkle
I am Chief Marketing Officer for The 20, which is The 20 MSP, which is a nationwide MSP, and also for The 20, which is a growth platform for managed service providers. So I oversee channel development, brand marketing, demand gen, content strategy, partnership expansion, public relations. And I've been leading marketing in the MSP space for over a decade.

Tim Fitzpatrick
Is that all you do? I mean, gosh.

Crystal Conkle
I have an amazing team.

Tim Fitzpatrick
Yeah. Well, that's, hey, as you grow, what needs to get done expands. So I love it. What's the most important thing you've learned along the way?

Crystal Conkle
Not everything has to be perfect. In terms of marketing, sometimes it's about being done and not perfect. And I think that so many wait and they refine and refine and refine in the moment passes. And you just got to move sometimes and get it out there. It's all about consistency versus perfection.

Tim Fitzpatrick
Yeah. I'm a recovering perfectionist.

Crystal Conkle
You and me both.

Tim Fitzpatrick
Yeah. Done is better than perfect has always resonated with me. Which leads me to my next question, right? We know marketing is... It's not easy, right? If it was, everybody would do it. There's ups and downs. Any mantra that you say to yourself or share your team to push through those times of challenge?

Crystal Conkle
One of my favorites would be, you don't have to feel like it, you just have to do it. I'm a big believer in taking action even when it's hard because the momentum comes from doing and not waiting until you feel ready. So in line with what I've learned that I mentioned previously.

Tim Fitzpatrick
Yeah, I love it. You know what a lot of people don't think about, too, is as we take action, we learn, right? It helps us start building momentum And once we have momentum, we just keep taking action. We learn from it, we adjust, reiterate, and we iterate, and we just continue to get better and better.

Crystal Conkle
Absolutely. That's how you figure out what works and double down on that.

Business Growth Through Acquisition and Organic Efforts

Tim Fitzpatrick
Yeah. I interviewed a marketer a few weeks ago who talked about ABT in marketing. We'll always be testing. Always be testing, right? And I talk about test, measure, learn. It's this constant iterative process. So I love it. Marketing is often cited as a challenge for MSPs. How have you guys approached building your marketing engine that supports your growth because you guys are growing through acquisition and organic efforts. How do you approach it?

Crystal Conkle
At The 20, we built our marketing engine with scalability in mind. We have done a number of acquisitions. We've done 37 in the last two and a half years. Again, it's about scalability, similar to what we do for our MSP operations. That would be a combination of strong brand positioning, consistent messaging, data-driven strategies. For the acquisition, specifically, our focus is on seamless brand integration, making sure that the companies that we're acquiring align with our identity while also leveraging their unique strengths. On the organic side, it's about creating a sustainable engine that drives brand awareness, that nurtures leads, reinforces trust. Consistency is key, but flexibility is as well, especially in an industry that moves as quickly and involves as quickly as the MSP space.

Tim Fitzpatrick
Do you have any idea... I love how you talk about on the organic side, just having a sustainable engine. One of the biggest mistakes I see MSPs make is they just jump right into the tactics. There's no fuel for the engine. They struggle to manage marketing. It's just like, let's just jump in and start doing stuff and throw stuff up against a wall and see what sticks. With your marketing engine, do you have any idea how on average, how long it takes people to move through the engine itself? How long do potential leads sit there before that are ready to raise their hand and say, I need help?

Crystal Conkle
Excellent question. It's different on both sides of the house with The 20 MSP, automated service provider. The benefit there is that you're getting a lot of clients who are at their moment of need. And that's why strategies like Google paper click are extremely effective because they're searching when they're looking for an MSP, when they have an issue, when they're not happy with their MSP, maybe they've grown and they want to outsource it for the first time. Whereas on the other side, with our growth platform, we find that MSPs do a lot of research before they end up deciding to become a member of The 20. It is a big change to their business, and so it's a longer buying cycle.

Tim Fitzpatrick
Yeah, because I think... So that's interesting. So on the MSP side, especially with paper click, you're targeting people that are further down the buyer's journey that are closer to buying. I think a lot of MSPs EPs, they're using tactics with the thought that people are further down the buyer's journey when they're not.

Crystal Conkle
Right. And we see that, too. And that's why it's important that your marketing strategy should encompass different channels, not just pay per click. You can't just do one thing. I always say there's no magic pill, but that's where drip emails, social content, all of those things work because they might be in a contract for a year, but you want to be top of mind when they're ready to make a change. And so you have to approach it from both aspects.

Tim Fitzpatrick
So part of that, all these pieces come together to create the engine. And If you don't have a way to nurture people and stay in front of them, you're not going to be there when that trigger moment happens. And that's where I think a lot of MSP struggles. They just don't have the engine to stay in front of people consistently, right? Because we can't create the desire to buy. It's a trigger moment that is happening going, oh, my gosh, my current MSP dropped a ball or I had a cyber attack. I need to do something different. Who is that? Who do you need to reach out to?

Crystal Conkle
That's why you see so much of what you described previously that I call the spray and pray method. A lot of MSPs don't have a marketing hire. They have an assistant or someone who's dabbling in it, maybe even an intern or one of their kids, and so they're not consistent with it, and so they're missing out on a lot of those opportunities.

Tim Fitzpatrick
You had touched on this. You guys have acquired a lot of MSPs in the last two and a half years. As you continue to acquire, how does that change your marketing approach, or does it?

Crystal Conkle
Great question.I think that our growth through acquisitions has forced us to be more intentional about brand cohesiveness while still honoring the local strengths of the MSPs we acquire. So early on, our marketing was heavily centralized in Texas, specifically the DFW area. But as we scaled, we adopted a more layered approach, which balances The 20s national brand with those localized marketing efforts. That way it maintains authenticity in different markets. We've also prioritized internal marketing, ensuring all of our employees are aligned with the brand vision, because obviously they're our most powerful ambassadors. Where that gets really, really powerful is through these rollups, the acquisitions that we're doing. Those are MSPs who have been members of The 20, most of them for years. And so they fully stand behind our brand vision, and it just it works really, really well.

Tim Fitzpatrick
So we're... Because of that, is there a lot of overlap in their tech stacks with what you're already doing in The 20 MSP?

Crystal Conkle
No, that's the great thing, and that's what makes these acquisitions so seamless. The reason we've been able to do so many is the integration is really, really, really smooth because they're aligned. I mean, it's impressive what we do within 60 days of acquiring them, but they're already lined up. So they're on the same tech stack. They're using the same sales process. They're operating the same way that we do because they're members of The 20. And so it's really, really smooth. In terms of marketing, what we find is a lot of them are not doing marketing. They're getting referrals, word of mouth. They've grown that way and plateaued. But you do find some who are doing different things than we are. And so we integrate that in, evaluate it. Okay, does that work in their market? Is that something that we want to add to our marketing strategy?

Tim Fitzpatrick
But... Because you guys already have that overarching marketing engine in place, once they're integrated in, they're just coming into the fold.

Crystal Conkle
Absolutely. It's just rinse and repeat.

Tim Fitzpatrick
I love your model because a lot of the companies that I come across that are acquiring MSPs do not themselves already have a marketing engine in place, which I think Well, you and I are biased, but-

Crystal Conkle
Absolutely. No, it's something I'm really passionate about. I think that you see a lot of that with the M&A activity in this industry. They're adding, they're lobbying on acquisitions, but they don't have that organic growth, and they think that they can overcome that with acquisitions, and you have to have both.

Tim Fitzpatrick
Yeah. Well, I was just talking to somebody earlier today who was talking about acquisitions, and he said that there's Depending on the company, there can be a fair amount of attrition with acquisitions, especially like at year two, three. So I don't know. My I guess, is based on your system, how you guys are doing it. You're not seeing nearly as much as some.

Crystal Conkle
No. That's the beauty of this model. Our attrition is very, very low. So the MSPs that we're acquiring, their clients are already familiar with us. Employees have been working in conjunction with the 24 years, and so attrition is super, super low.

Tim Fitzpatrick
That goes back to your point about focusing on brand, right? And so It's not, oh my gosh, they just got acquired, and now we're dealing with so and so. That creates a lot of uncertainty for clients, right?

Crystal Conkle
Absolutely. It makes the communication process very, very smooth post acquisition because they've already seen that name. A lot of our members use a logo under theirs as powered by The 20. And so our help desk is an extension of theirs. And like I said, their clients are used to interacting with The 20 help desk. And So really, it's just very small updates and name, logo, billing. And they've been very, very happy with it because they're happy with the service that they receive from The 20.

Tim Fitzpatrick
Yeah. So they Even if they're not intimately familiar with The 20 MSP, they've seen The 20 in the acquisitions branding in some way, shape, or form, or their interaction with that company. They've seen The 20, so it's not something new.

Crystal Conkle
Right. And for MSP members, like I said, they're familiar with the logo, and they'll see it on their shirts. Like the MSP will have their logo on the chest and then The 20 logo on the sleeve. We understand what it is. They're using it in their sales pitch, too. That's one of our most powerful offers for MSPs in joining The 20, is they're able to go out and close those bigger deals. And so they're very transparent about being partnered with The 20 because it expands their capabilities and they can take one much larger clients than they could otherwise.

Tim Fitzpatrick
Yeah. So they're using it to position themselves like, Hey, we may be an MSP of 10 people, but we've got all these resources behind us.

Crystal Conkle
We have offices nationwide. If they have multiple locations, we can support you in any city in the US, Canada. It makes the sales process really incredible. It gives the edge for sure.

Tim Fitzpatrick
For MSPs that are joining The 20 group, how is that structured? Are they paying a membership fee? What do they do?

Crystal Conkle
No, they don't pay a membership fee. It's all consumption-based.

Tim Fitzpatrick
Okay.

Crystal Conkle
So they're using the CAC stack. We did acquire collaborants last year as well. Previously, we were at Kaseya House, and now we've expanded. We have members who are on Kaseya Stack, also on ConnectWise.

Tim Fitzpatrick
Got it. So they're paying for the services that you guys are helping them fulfill.

Crystal Conkle
Correct. At a much better rate. We're getting much better pricing than they can get on their own just because of volume. So it's a single funnel buying

Tim Fitzpatrick
So it helps them leverage the power of many, even though they might be quite small.

Crystal Conkle
Absolutely. They're getting the price that someone would get with hundreds of thousands of endpoints versus their maybe 200 or 500.

Marketing Tips for MSPs

Tim Fitzpatrick
I love it. So for MSPs that are struggling with marketing, what would your top three tips be to help them?

Crystal Conkle
I think number one would be consistency over perfection. We talked about before, too many MSPs and too many people think that marketing has to be perfect, and so they get stuck waiting for that perfect message, for that perfect content. And it's so much more important to focus on consistent, authentic communication, whether you're working on content, social media, email marketing. Like I said before, marketing doesn't have to be perfect. It just has to be done. Number two know your audience. Don't try to speak to everyone. You can't be everything to everyone. So it's very important to clearly identify your ideal client and to build your messaging around them so that it speaks directly to their pain points, their goals. That way, when you're creating content, it's about solving their problems.

Tim Fitzpatrick
Yeah, I love it. And by the way, for those watching listening, I did not pay Crystal to say that. When we talk about helping clients build the marketing engine, the first element in strategy is your target market. Who are you serving? Who are your ideal clients? And from there, once you understand them, then you can create a message, right? Because a lot of MSPs are targeting far too broadly. Their message is too broad. It looks the same as everybody else. And you cannot create a good message until you know who the hell you're trying to reach.

Crystal Conkle
Absolutely. That's always be the foundation. Then third, I would say measure and adjust. Marketing is not a set it and forget it function. Track your metrics, analyze what's working, figure out what's not working. That way you can double down on what is working. Always be willing to adjust and pivot. The best marketing engines are built on data. That way, when you figure out what works, create scalable processes around it and continue to refine and improve.

Tim Fitzpatrick
Measure and adjust, right? We make mistakes all the time as marketing. Most of the marketing we do, it doesn't work. But it's that testing and that constant iteration that helps us get to what works. I want to, related to you mentioning know your audience. Given that you guys are acquiring people, MSPs all over the country, you continue to grow. You're serving across various industries. How do you approach marketing to a broad audience? Are you very specific with certain campaigns? How do you do that?

Crystal Conkle
You're absolutely right. The 20th Client base spans essentially all verticals. We're talking financial services, legal, nonprofits. That list just goes on and on if they're green. We take a hybrid approach. Our core messaging focuses on universal business outcomes that will resonate across industries, so security, efficiency, growth. But within that framework, we tailor campaigns so that they address industry-specific pain points when necessary. So I think it's all about balance, that unified brand strategy that can flex to meet the nuanced needs of different verticals. And really, when you're talking about that in terms of IT, that's just the application layer. The foundation of managed IT support is the same. I mean, managing their services, their servers, all of that. So we also rely heavily on storytelling, on showcasing client success, stories that highlight our impact in different industries, but without diluting the core brand.

Tim Fitzpatrick
Yeah, got it. So I want to reiterate this. From a messaging standpoint, universal business outcomes, which look, in reality, they don't want the same thing, right?

Crystal Conkle
They just want their IT to work.

Tim Fitzpatrick
But the messaging is targeted on specific campaigns that you're doing. So whether that might be... I mean, it could be content that you're creating, it could be specific Google Ad campaigns, that stuff is much more targeted.

Crystal Conkle
Right.

Tim Fitzpatrick
Got it. And what about with email? Are you segment... With such a large audience, are you segmentingyour audience into verticals? Are you getting that deep into it?

Crystal Conkle
We are. Obviously, we have an overarching drip campaign that focuses on those core issues we talked about, but we have segment in it and are targeting particular industries.

Tim Fitzpatrick
So you might send a specific industry case study to that specific?

Crystal Conkle
Right. It would have maybe a video. We have industry-specific case study videos, so it include a video or link to a landing page focused on their industry.

Integrating AI with Marketing

Tim Fitzpatrick
Yeah, cool. I love it. Let's talk about AI. We can't talk about marketing without talking about AI, right? What are you guys seeing? How are you utilizing AI within your marketing efforts?

Crystal Conkle
I would say AI has already greatly transformed how we approach content creation data analysis, even lead gen. We've integrated AI tools to improve efficiency, so drafting, editing content, optimizing campaigns in real-time. We've also seen AI-enhancing products that we're already using, so So for example, HubSpot, Google Performance Max has been incredible for pay-per-click, Microsoft Copilot, a lot of really great tools. But it's not just about automation, it's about amplification. AI has really helped us scale efforts without losing the human touch, because I think that is so, so critical in B2B marketing. Moving forward, I really see AI playing a bigger role in predictive analytics in terms of enabling businesses to anticipate customer behavior, to optimize campaigns, to personalized content at scale. I think that that will drive hyper personalized marketing and dynamic content strategies that are able to adjust to adapt to audience behavior in real time. And so, again, the key, I think, is to use AI as an enhancer, not a replacement for authentic connection. You don't want to lose that because that's the heart of your marketing.

Tim Fitzpatrick
Yeah. Do you For like with content creation, are you using any specific tools that you guys like with AI for that?

Crystal Conkle
Like I mentioned HubSpot has great built in tools. When we're doing things in HubSpot, we use those that are built in Microsoft Copilot, ChatGPT, Cloud. I feel like the list goes on and on.

Tim Fitzpatrick
There's so many.

Crystal Conkle
And I do love, like I mentioned, the tools that we're already using that are integrating AI. And I think we're going to see more of that. And that's what we need to be looking towards to really future proof our marketing strategy.

Tim Fitzpatrick
Yeah. With analytics, are you using AI to analyze analytics within tools like HubSpot already, or are you actually taking data out of those and putting it into a ChatGPT to have it analyze that data? How are you approaching that?

Crystal Conkle
Great question. A combination of both.

Tim Fitzpatrick
Good. Yeah, so sometimes you're actually taking data and then popping it into ChatGPT and just start asking it questions.

Crystal Conkle
Right. And I always caution people, be careful what you're putting out there. I mean, most people are using the paid version anyway, the professional version. And so it is more secure. But just be careful what you're putting out there. Don't put out any proprietary information.

Tim Fitzpatrick
Yeah. And make sure that you're not sharing your data to train the model, right?

Crystal Conkle
Exactly. And then search. Search gets me really excited in terms of AI. I think that it's become so important to position your business to be recommended by AI tools like ChatGPT. That way, when prospects are searching for an MSP, you're going to pop up. And so what's key there is creating content that AI can pull from. We're seeing more of that. And it's different than Google, because unlike Google and traditional search engines, the AI model is prioritize that natural conversational response. And so you want to optimize for that.

Tim Fitzpatrick
I want to break this down a little bit because I think this is a really good point. What was happening before AI, right? Was you're creating content so that you can rank in search so that when somebody goes to Google, they see you listed there and they click on that and it takes them to that particular article or that page on your website. That is starting to shift with AI use, right? Because people are going into tools like ChatGPT or Perplexity or whatever it may be to get information. So they may not be clicking through to go to your website. But if they go into a ChatGPT and say, Give me the top 10 MSPs in Dallas, you want to show up there. What you're saying is content still plays a vital role in your ability to show up in searches like that through AI. Is that right?

Crystal Conkle
100%. When you think about AI visibility, it's about creating that relevant high-quality content, getting listed by trusted sources, and really ensuring that your brand has a strong digital footprint. Because if that's not out there, then AI has nothing to pull from. I think this is such a huge opportunity, and most businesses aren't doing it yet. And so I think that those who jump on this and move fast have a real competitive edge.

Tim Fitzpatrick
Yeah, it's interesting. I also think that it's also going to make social a lot more important. The content that you're putting out on social, that's another way that people are going to find you. And if you're not consistently out there posting on social, I think you're going to be missing out.

Crystal Conkle
Oh, I absolutely agree. And I think that's twofold. And that ties back to AI, too, because when you're active on LinkedIn and those industry forums, that's where AI tools are finding their insights.

Tim Fitzpatrick
It's just pointing to the importance of taking an omni or multichannel approach with your marketing. You can't rely on just one thing or two things. You need to be consistent across multiple channels.

Crystal Conkle
Yes. And social, like you said, it's so important in that human aspect of it. That's where people are able to scroll and consume your content as they come across it, their day is not being interrupted with a call, email. And so it's super, super important.

Tim Fitzpatrick
Yeah. So even though content creation moving forward may not drive as much traffic to your website, to that particular piece of content, content creation is still going to play a critical role moving forward.

Crystal Conkle
Absolutely. Yeah.

Conclusion

Tim Fitzpatrick
I love it. This has been fantastic. I want to ask you one last question before we wrap up. Knowing what you know now, anything you would do differently?

Crystal Conkle
Honestly, I've always believed in going all on marketing, and I don't regret that. But if I had to do something differently, I'd move even faster. In hindsight, which is always 2020, there were times that I knew the right move, but I hesitated, whether it was launching a new campaign, shifting a strategy, making a key higher, growth reward speed. And I've learned that when you see the opportunity, take it, jump on it.

Tim Fitzpatrick
Yeah. Risk versus reward, right?

Crystal Conkle
Yes.

Tim Fitzpatrick
Crystal, thank you so much for taking the time. I appreciate you doing so. Where can people connect with you?

Crystal Conkle
Thank you, Tim. I've enjoyed this conversation. The best method for reaching out, connecting with me is LinkedIn. I think you're adding my LinkedIn. Yeah. I got your ads on there. And then you can learn more about The 20MSP at the20msp.com. If you are a managed service provider, you can learn more about The 20 Growth platform at the20.com.

Tim Fitzpatrick
Cool. I love it. We'll make sure all those are in the show notes. And if you want to connect with Crystal on LinkedIn, do that. And it's Crystal with a C and then Conkle with a C as well. But we'll make sure all those links are in the show notes so you can connect with her. And thank you again. I appreciate you taking the time. I know there was a ton of value that you shared here. And hey, if you're an MSP, there's a ton of value here, even if you're not, the fundamentals that we talked about today are applicable no matter what. So thank you, Crystal. I appreciate you.

Crystal Conkle
Thank you. Great conversation.

Tim Fitzpatrick
Awesome. I appreciate it. And those of you that are watching and listening, I appreciate you as well. If you want to connect with us, do it over at rialtomarketing.com or over at revenueroadblockscorecard.com. When we help clients build their engine, we focus on nine key components. If you want to know which of those nine are slowing down your growth, that's where you can do it. So go check it out. Thank you. Until next time. Take care.