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How Top HubSpot Partners are Scaling Operations with ClickUp

ZenPilot on ClickUp


ZenPilot co-founder Gray MacKenzie shares deep experience from helping over 2,600 marketing agencies to improve operations and scale.

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ZenPilot is a training and consulting business that helps digital agencies build more productive, profitable, and healthy teams by streamlining their operations in ClickUp.


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Direct Transcription of Podcast

Greetings everyone a very warm welcome to another edition of the HubDo Podcast, where we're talking with software vendors, subject matter specialists and end users who share real stories of how to do more on HubSpot. I'm your host, Pete Nicholls. I'm coming to you from Copenhagen in Denmark, and I'm joined today by Gray Mackenzie, Gray, good day, mate. How are you doing? Where are you coming from today?

Uh, I'm coming from Pittsburgh, Pennsylvania. Pete, I recently listened to your, you had Qwilr on the podcast and I hadn't listened to a HubDo episode in a while, and I heard you say "good day, mate". I was like, oh, this is just Pete's greeting for someone who's in Sydney. And then it turns out it's not actually true. That's the greeting. I love it!

Haha, I got mates in Pennsylvania. I got mates everywhere. So yeah, an official "Goodday mate". Uh, let me give some background then to the listeners. So a little bit about Gray. So Gray McKenzie is a true operations nerd. You have a passion for helping digital agencies, and building healthy, productive, and profitable teams. I know you've built ZenPilot into ClickUp's largest and highest-rated implementation partner. And you've spent the last decade helping, its an incredible number of over 2,600 agencies to streamline their operations.
And, uh, there's a bit of background you've uh, you've got how many kids.

Yeah, we've got, we've got four young kids, seven, uh, seven down to one.

And travel as well, that's kind of your thing too, although you haven't been traveling during COVID so much.

Not, not really. So yeah. Adventure adventures of families are, is awesome.

Well, it's an open door here in Denmark mate. Say, you know, come on over when you fancy having a more expensive beer, the beer is cold. Uh, the, the welcome is warm. So we're, we're delighted to include ZenPilot on the HubDo Podcast and HubDo Marketplace so that people can do more on HubSpot, but we should really help people if they haven't come across, ClickUp before, what is it, Gray?


A typical question here, the category that we put it into is a project management platform. You think of Asana, Monday, JIRA, Basecamp, Trello, you know, any of the platforms out there. I think there's this movement. You've probably seen this from teams like Monday to say, you know, kind of break out of the category and try, they know we're working management software or where, you know, work efficiency software.
So the category. I don't, I don't think that that to, to the average user, to me, doesn't really matter that much, whether we call it work-management or project management, but it's meant to be that place to house all your projects. If you are, uh, working a service-based business, like an agency, you know, how do we manage all our client projects and make sure that all the works getting out on time and then internally, how do we manage operations as well.


So folks who are moving to ClickUp have probably been using Asana or Trello or Basecamp or one of those project management tools and then they're looking to ClickUp, which looks to be particularly suitable for agencies to use. And we're gonna dive into that. So the name of our episode today is "How top HubSpot partners are scaling operations with a ClickUp”. So let's dive on in, help me out with this first Gray, what types of agencies do you think are an ideal fit for ClickUp, and who maybe isn't a fit?

The types of agencies that it works really well for though, I think because of the power and flexibility, like whether you're a retainer shop or you're a project-based shop can work really well.
The folks who I point to other platforms are the folks who want, have wanted an all-in-one system that does my invoice in that does my, you know, finance, uh, component that does all my time trackings in ClickUp, but does all my time tracking and profitability reporting and everything else, like folks who are looking for the all in one are a better fit for Excel or, um, you know, some of the other, other platforms out there. And I think obviously there are trade-offs in that equation. Like, Hey, we're giving up some best-in-class tooling for project management specifically in order to have a wider feature set. So, um, yeah, ClickUp is the fastest growing PM platform in the agency space. I think it's because it's got a lot of flexibility to fit a lot of different use cases.

Where do you think the tipping point is then if you talk about the number of staff, just gut feel for you, you've dealt with so many agencies, if maybe one or two people is a little bit small, perhaps for the complexity and capability of ClickUp. At what point does ClickUp become a good fit?

Yeah, I think, uh, every team, you know, we all hit that point. I think people have different capacities for where it's too many people for one person to manage, but most people would say that's somewhere in the five to eight range. At that point in time, you need some system somewhere, like, is that ClickUp or is that another platform? I think you can, you know, there's a lot of good options out there, but that's the normal point where I'll be like, Hey, you should, you really need to start thinking about the investment that you're gonna make. You're gonna make an investment one way or another. It's not an option. It's either we're gonna deal with more chaos and no system to organize at all, or a poorly thought out system to organize it all.
Or we're gonna deal with less chaos, chaos, but we're gonna make an upfront investment to get whatever our PM tooling is. Correct. And so I think at that point, That's where it really starts to, to come back to bite agency owners and, and team operators is once they hit that tipping point where it's beyond what one person is gonna mentally keep track of and manage.

And if you hang onto the system that you have for too long, then that becomes a whole, you've gotta dig, dig your way out of while you're struggling with, uh, with overload already. Again, having worked with so many agencies, Gray, what, what are the common mistakes that you've seen people make either before they come and implement to ClickUp or, or maybe touch on some of the expectations that were wrong and, and that mistakes were made around, clip up, ClickUp as well.

I think there are three key pillars to getting this right for agencies. You've got obviously the technical side, which is for us where ClickUp, comes into the picture. Like what's the tooling that we're using? How do those tools talk to each other? Um, You've obviously more than pretty much anybody who I talk to is tied into all these different platforms and how they work together and how can we pass data back and forth between whatever it is we worked with you to make Panda doc talk with HubSpot and connect.
So that's a tooling problem. But the other two pillars here are the process side. Like how do we actually work? Does everyone follow the right and best process every time to deliver work efficiently and high-quality work for clients? And then the behavioral side, which is how does our team operate? What are the rules of engagement, um, and expectations around that? Having a great PandaDoc to HubSpot integration doesn't matter if the team doesn't know it exists or doesn't know how to use it. Um, and the same thing procedurally, like if our templates are crap, then it's still, we're efficient getting it out there, but it's, it's a low-quality outcome.

You know, I think when, if we just say the word project management everyone's mind goes instantly to the tool, like, oh, do I need ClickUp or do I need Monday? And you've got folks like us in the marketplace who are adding to the noise by saying, look at all the cool things ClickUp can do. And then, the truth of the matter though is none of that matters if you don't get all three of those pillars right together. So the most common mistake is we invested all this time, researching tools. We picked a tool and we forgot to tell the team here is exactly how we expect you to use it. And here's our culture around how we're gonna manage projects. And we invested very little time into creating standardized templates in net tooling for how our team's going to deliver work, that we can easily deploy. And the team knows how to use those and follow those processes. So I think those are the two most common mistakes and we can go, I'll let, I'll stop here, but I'm happy to go deeper into like, Hey, what is specifically, people get wrong in ClickUp or struggled to get right in, ClickUp, or what do the better agencies get right out of the box. But does that resonate? Those kinds of three pillars?



It does, uh, when we talk about three pillars, I think of like a tripod, any one of those three, if it fails, the whole thing fails. And I'm thinking with the simplicity of tools like Asana and Trello, that sometimes you can also be led into a false sense of preparation in that, uh, those tools let you go a long way without having to define that much strictness around your processes. On the behavioral side, people may be quite flexible in how they use those tools. So with ClickUp, then you are you really needing to buckle into something that's a bit more structured. And, uh, that also can be a people challenge, getting people saying, oh, why does it have to be so hard? Whereas they're coming from an environment that maybe its flexibility was its weakness. Would you say?


Yeah, I think that that's definitely true. I think there are a lot of implications and ClickUp in their own marketing. We'll say, Hey, we want to create a platform that works for everybody. You can, Pete, if you wanna work in Coban boards and whatever else, and Gant charts, that's fine, and Gray ones to work in tables and lists cuz he's a nerd. That's fine too. Um, and, and from a view perspective, that's totally fine where you run into problems is as an agency specifically we're just creating all this data in the day-to-day in what we're doing. We're creating tasks and we're tracking time to them. And all of that should wind up being an asset to help inform better decisions for the future. But if I let you go, Hey, pick a, pick a space inside, ClickUp and go create it however you want to get your work done and I'll go create mine. However, we run into a huge challenge when we try to pull any meaningful insights from that because our data's structured in totally opposite ways and you're not tracking time at all. You're tracking time up at a project level and I'm tracking time down at a subtask level or more granular level and not trying to mix and match any of that and understand what clients are, are most profitable for us. What clients are least profitable? When we do this service line, are we losing money in this service line or are we making money? We don't get any of that ability to capture any of those insights back out of it. And then we had the complexity of adding more people to the team and their work habits are directly informed by who they happen to train under. There's no one standard for how the business does things. So you wind up with everyone's got their own spin on how work gets done. There's naturally going to be, Hey, something went wrong here. This person's gone. I have no idea how to go find what happened or what needs to happen next, or how, how do we work together. How do we cover for each other when someone's outta the office and when there's turnover or somebody new coming on board, it's super hard.

You're just, you will pay a cost one way or another. And the cost will just be in a lot of that chaos and drop balls. Um, if you don't have some standardization around, here's the way that we as a team are going to work together.


And given many agencies have a bunch of folks who would call themselves creatives, what creatives love structure like, let's stay creative.

Uh, so ClickUp is all about making the business more successful and, and scalable. So, uh, some of the things that have gone wrong or have gone, right, I'm keen to unpack that and some of the real stories that we'll get to in a second, let's talk about HubSpot for a moment. You are focused on HubSpot partners. Can HubSpot do anything in this area before you go adding, uh, a tool like ClickUp? How far does it go?


Um, it can, um, obviously you're into the projects tool inside HubSpot as well. There's a long, we've got a very personal tie in HubSpot projects from our days back building software and, um, being a HubSpot partner, um, So HubSpot projects, you can create tasks, you can have templates. There are some like very, very light project management capabilities really struggle in an agency ecosystem because each of those is run in a HubSpot portal. Um, and they're all siloed into their, you know, there's no way to go get an overview of I'm in 20 different client portals. Well, how do I see everything that's going on across the board?

There's certainly some light stuff that can happen there. I think for in-house teams I've and back in the agency days like we've worked with some in-house teams who are using HubSpot projects, um, somewhat effectively, but as a true project management tool for an agency managing different clients. Um, yeah, I would not recommend HubSpot projects as much as I love HubSpot for true agency project management.


I think you hit the nail on the head as a key reason where HubSpot's built-in project management might be fine for an end user because they're only ever working in one HubSpot portal. But if you're an agency that's jumping between customer portals, that's a separate project management system in each one. So you do need some kind of an add-on. Now, um, most of the tools that we've mentioned, they integrate with HubSpot in some way, the likes of, uh, of Asana and, and Trello and so forth. ClickUp has just beefed up its HubSpot integration. Could you tell us a bit about what is now there that you haven't had the luxury of before, Gray?


Yeah. So for a while, teamwork has been the leader of the pack in terms of the direct integration in HubSpot. There's not really, for most other platforms out there, there's no direct integration or ability to trigger work. You know, when something happens in HubSpot trigger, something to happen in ClickUp or whatever, then, the platform is.

And so this is in beta right now, as we're recording it, I'm sure as a lot of folks are listening to this, they'll be able to access this and get into it. But, um, V1 of integration between, um, HubSpot and ClickUp is direct. So, or is built and available in beta right now. We've been using it, um, for a while here internally, and it's starting to replace some of what we're doing we do a huge amount of workflow automation between platforms, um, at ZenPilot we use for a lot of that integration work and so the HubSpot thing is HubSpot's the most popular CRM that we are, um, helping teams integrate and that connection between a CRM and a project management system is really important.

So using HubSpot's native workflows tool, we can now say, you know, when a deal gets moved to a closed one, I wanna go create a folder in ClickUp, or I wanna create a task from a template in ClickUp and it needs to have these properties passed through from HubSpot, um, and push that stuff, um, back and forth. And eventually, you know, that'll be bidirectional, or there'll be the ability to also trigger workflows from ClickUp, back into HubSpot, but the V1 is out and live now. And that's, you know, the most, that's probably the most common use case that we're helping agencies set up, is for any engagement, any client services business that gap between when somebody pays us money and signs up and they get that first activity or the first feedback, um, loop, there can be a lot of anxiety and there's a natural period of buyer's remorse that happens there. Um, is anything happening? I paid money, like, do I, I'm worried about getting value back out of this, and minimizing that time to value is huge for a great client experience in building trust. So having a really smooth handoff from a client just signed up the deal, got closed in HubSpot to, Hey, the project is set up, the client's getting that welcome email, they're, you know, all the details are right. The team's assigned inside, ClickUp. That's really important. And so that's the most common workflow that we're creating right now using that integration.


That's a really quick response. As soon as the deal is done. It's a kickoff call or whatever the next alert is. And the customer's like, wow. Okay. Um, things are moving already. There's no, uh, ticking and waiting, uh, like the expectant dad outside the delivery room. You and I have both been there. Right. So let's, uh, let's look at some real examples. So whether it's around the three pillars that you mentioned earlier or anything else out of this playbook that you've built. I'm, uh, amazed, the guide that you've put together for agencies to use with, with ClickUp is clearly a lot of coalface trenches learning in there. Can you give us some examples? Uh, don't have to mention the agencies of course, but, uh, what are some real scenarios that come to mind.


I think in the HubSpot ecosystem, I so some of the like top part, some of my favorite partners, and I shouldn't probably say favorite partners cuz we worked with hundreds of HubSpot partners and I don't wanna leave people out, but I think it seems like they're all your favorites. Exactly. seems like, um, Mojo Media Labs who is recently acquired by Gravity Global, or Lean Labs sticking with the lab's theme or Beacon Digital Marketing. Um, you know, and that list could go on but some of the commonalities, I think of some of those top partners, is that there's already a commitment from the leadership team too, we want, like we're already bought into the structure and building the infrastructure to scale. Um, we just haven't figured out how to make that happen in the project management and operations, and delivery side of the business yet.

And so I think the common, almost everybody, we've kind of pivoted our market. This is a little bit kind of behind-the-scenes at ZenPilot. We've pivoted some of our marketing where a couple of years ago it was very much around the boring stuff. Hey, there are these three pillars; there's technical and procedural, and behavioral. And it's like, who cares? Are we in a science lab somewhere? um, what's going on? To lead more with ClickUp because when most people think of solving this problem, the thought is the tool like I need a different tool and agencies are infamous. They jump tools on average, every, little less than two and a half years from one platform to the next.

And if you talk to any agency owner who's been in the space for more than five years, they've been on, you know, at least three different tools, 90% of the time. Um, So that's common, oh, this is painful. Must be that the tool's not working for us and it's not wrong that the tool's not working for it, but they do not work, you know, the work hasn't been done to make the, um, to make the tool work either. So we've shifted a lot of our marketing towards the ClickUp side, um, which has worked well. And the guide that you mentioned has been really helpful too, um, to thousands of folks, which is cool to see. I just got a couple of messages last night from people who were like, Hey, I went through this, I'm doing, later today I'm doing a Twitter space with ClickUp talking about how agencies should be streamlining product management on ClickUp. And, uh, so as they were promoting that, I just got a couple of messages from folks who were like, I went through that guide nine months ago and it was so helpful as we set it. Um, so a lot of the marketing has become around that too, um, to kind of get people's attention, obviously, but then we're going through an education process to say, Hey, this is why most people are coming to us is for the technical side, what's hidden beneath that is the best ClickUp set up in the world that doesn't have the right process templates built, or those process templates are built and they're just the wrong process. Doesn't help. Those templates were built, but nobody knows how to actually apply or use them, um, has been huge. So some of the coolest stories have been, um, with, uh, an agency of about 25 people. They came in and worked through the process, uh, the click, they were on ClickUp preexisting, the ClickUp setup actually wasn't terrible. Um, They didn't have any standards for how the team was all gonna use the tool together. And so it was very hard to get any insights rolled up to the leadership level and then their process templates. They already had some process templates built, but they all had been built by somebody on the project management and ops side of the business, not the people who were actually the best at doing the work.

And so we went through, we went through kinda this three-step process of designing, um, What, what things needed to look like from a process perspective and from a technical perspective, and then from a team perspective, and then taking that and implementing that in, uh, in phase two. And the third part was just kind of optimizing that.

And in that implementation phase, it was a lot of pulling in the subject matter experts and saying, that's fine that you don't know how to build out perfect ClickUp templates right now. Like, well, that, that playbook is really easy to solve. What's hard to solve is, is like you have this expertise and you know how to do things better. A lot of these junior folks aren't getting that training. They're following a template that was created by somebody else. So they had with the same staff, um, or a same number of headcount, there was some staff turnover that happened, but they were able to increase the revenue managed by 350% with the same exact headcount.

Um, so just like crazy numbers be like the amount of profitability growth that happens there. And obviously, then the ability to pay people better and retention went up, um, as a part of that engagement as well, but getting the right processes built in the tool and then getting the team was, and that obviously that happened over about a seven month period, the right processes built into the tool was a big chunk of it.

Getting the team all trained on how to use it and how to understand what that all meant and kinda clarity on what in the day-to-day, what am I supposed to be doing? And then the optimization part was huge to be able to have insights back from what was going on and then move people into their zones of strength, um, as they had data and cut and reprice service lines, um, based on the data, actually coming back about what the costs were to deliver it. So, um, those, those types of results are super exciting I think often that's a case with a younger agency where there's just not a lot of optimization. A more mature agency is rarely gonna have a 350%, uh, increase in basic profitability with the same team or the revenue managed by the same headcount.

But we'll often see there is. The infrastructure is in place to scale smoothly. And so a team like Beacon Digital Marketing, as they doubled in a year, um, which is hard for any service-based business to go through much easier in the software space than in the services, um, business and the number of the types of problems that you're solving look totally different.

It's kinda the first time Whitney and the leadership team there felt like, Hey, we've got the infrastructure in place where we can really, um, we can absorb this and we can continue to deliver really high-quality client results at scale. Um, so there's a lot of, a lot of different examples like that of different types of impact that it's had on different agencies, but they're all following the same framework of kinda getting all three like that's the commonality. Even when we look at teams who haven't worked with us, they haven't gone through that framework. You look at what's working well. That's always in common. It's like, Hey, they've whether it's by accident or by intentional design, they've gotten those three pillars right.


Do you see that often where processes have been put together, but actually nobody could really follow them because they've been written by an operations person rather than someone who really knows the tools? How often does that come up?


Um, I'd say there are fewer, that's probably the majority of cases where processes are built. So you go to any of these conferences, you were just at Inbound obviously, and every agency who's like, I remember going to HubSpot's partner day for a year is back in the, you know, 2012 to 2018. And every agency that had hit any type of scale, that's why they would say it's like systems and processes. So that buzzword is out there everywhere. But what the heck does that actually mean? It's really hard to do. And when you say that to a bunch of creative people, no one gets super excited.

I actually think there's a lot of, um, creatives are really grateful people for folks who bring that structure when it's explained and articulated well. And when it's not, it feels soul-crushing and there's a lot of disdain, um, towards it. Mm-hmm, but that's kind of surprised me that there is a lot less resistance when the, when the value prop is articulated clearly and, uh, here's the, here's the result and here's, here's the benefit to you that comes out of it. So I would say for the majority of agencies that we talked to, if you looked at what percentage of their current um, deliverables that they produce for clients they have an actual documented process for it's well, below 50%, most people have not spent most of the time, but the folks were, the majority of those are documented. The majority of the time it's been documented by somebody who's a project manager or who's a, um, who's an operations person and that's not always a problem if they do the interview right. And that gets. Hey, we know how to interview our team to get that. It's just like creating content. You get a lot of junior marketers, first three months on the job, creating content without talking to a subject matter expert, content's gonna suck. Mm-hmm, it's not gonna be that helpful, but you take that same person and give 'em a really clear playbook for here's how you're gonna get the right content from people. And then you use your marketing skills to go package that together. That recipe can work really well, but often, yeah, that's a common, a common pain point, right now.


So getting those processes together, it's fine. If ops do that, in fact, ops people are probably the ideal ones to make that happen and happen well, right? But they've got to get the input from the field teams that are doing the work to make it real. And you've also said the creatives really welcome the processes if someone's gone to the trouble of putting it together. And there's a value proposition there, if you can think of as a final example then of, um, where you've seen an agency develop great processes and you think like that's the gold standard. That's what every agency does. If everyone did that, it'd be perfect. What comes to mind? What was the secret source there for that agency of why it happened that way?


Um, there are kind of, I think, four. and I know when you're explaining this, you should never put a prefixed number on things if you don't already have them all memorized. But, um, the first piece was a culture of documentation from a leadership level. Um, not necessarily that they did it, but it was clear to the whole team that documentation. And they did some of it, but it wasn't like this agency or just sitting around documenting things all day.

Um, but they built out good things and they'd rewarded the team and already had a culture in place before we got engaged with the agency as, a 40-person agency here in the States. So a culture of we're gonna find the best practice and we're gonna standardize that across the team ahead of time. We're missing kind of, how do we connect the dots to make that actually happen?

But, um, but there was already a culture of it. Um, Then there was a clear scope or clear mission. What are we trying to accomplish? In that case? It was a productivity improvement. Like, Hey, we need to figure out how to get 30% more productive. We need to like everyone is saying that we're overworked right now. Our time tracking is consistently in the low 40 hours of work per week and that's not even all the time tracking that we're doing. Like we'd like that to be 35, or 36 hours as a target. How do we um, how do we reduce the amount of time tracking that capture all the time that we have, but reduce the total amount?

Um, that looks like so clear targets. And then I think the next piece from a process perspective was just being willing to step back and also get kind of the team. The team was already aligned on what the goal is that we're trying to get to, but not just go to one of the best, you know, at a 40-person agency with a focused skill set. You've got multiple people in roles. So it's really important that you don't just go to the person who's been there for the longest and say, how does this process work? And then document that and say, okay, now everyone's gonna do it this way. And there's not already some consistency there. So there were kinda the interview and just the collaboration process to get those, um, documented.

There's a huge art. There's like this should be a book at some point, which is like the hidden art of how to efficiently get processes out of people's heads and agreed upon by all. Um, but, but that was because of the culture that was relatively easy to do with the right process. And then they built it all out and trained the team. Uh, so they were all built out in this case, obviously on ClickUp process templates, which can live at multiple different layers and ClickUps hierarchy, and the whole team was trained on, Hey, I'm creating a quick task. And the task, in this case, is a, you know, it's a new blog post for a client and they learned how to, how to quickly deploy those. So not there's a, it's probably too nerdy to get into, but there's a way to use templates in three seconds or a way to use templates and take a minute to go deploy and they trained everybody on the fast way to do it, which meant that buy-in to be able to do that, um, was a lot faster. And then obviously holding people accountable, like measuring that, having a quantitative way to measure that was really important and share progress as they went.

So I think those are the steps like buy-in a clear culture of it from the top, a quantifiable goal that we're shooting for that aligns a team, a process for getting that out of people's heads and then training and, and account.


Brilliant. So, I mean, you did better than the four that you had you actually, I count five points.


We cheated.


You've over delivered. Um, and it sounds like there's a book on the way then there should be because there's like, uh, Zen in the art of motorcycle maintenance, uh, ZenPilot, you guys, ZenPilot, and the art of how to get processes out of people's heads and get everybody to agree to them.

That's right. It just rolls off the tongue there. As a final wrap-up then, Gray. Thanks for sharing that. You've got so much experience working with agencies and you, by being focused on HubSpot and ClickUp, then you, you just honed that over time. And I know that's in the guide. We'll have a link in the show notes, so people can go and, and get them, how to implement, ClickUp for agencies guide and download. For those people who wanna get in touch with you, Gray, what's the best way to reach out to you? Is it linked?


Yeah, LinkedIn is great. Um, Gray Mackenzie or email gray@ (G R A Y)


Fantastic. Well, thanks for sharing all that experience with us, Gray. It's been great to have you on the show.


Awesome. Thanks, Pete.

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