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Client Story: How George B. Thomas and Sidekick Strategies Nailed Their ClickUp Setup With Our Blueprint

Jakub "Kuba" Grajcar is the Content Marketing Manager at ZenPilot. His obsessions include interviewing smart people; productivity methods; project management; and playing bass in a progressive metal band.

Picture this: you've built a successful business as a solopreneur, but the amount of incoming client work ramped up fast and it's tough to keep up.

You've hired a team to help, but without clear processes and organized project management, delegating is a nightmare, and work visibility is... not great.

Sound relatable?

George B. Thomas, CEO and founder of Sidekick Strategies, found himself in this very situation.

But with the help of our humble team at ZenPilot, he transformed his business into a thriving agency with streamlined operations.

In this story, we'll explore how he got there.

Watch the full video version below to also get George's #1 tip for agency operations:

Otherwise, read on for a compressed text version.

George's journey with HubSpot began back in 2012. "I used to be a designer developer guy," he explains. "A six pack of Coke and a pizza would come in one side and a website would come out the other."

After attending the inbound conference and hearing HubSpot's human-centric philosophy, George was hooked. He dove into HubSpot Academy certifications, eventually becoming a HubSpot accredited trainer and even starting the first HubSpot-specific podcast, the Hubcast.

From Solopreneur to Accidental Agency Owner

In 2014, George decided to step out on his own as a solopreneur, offering HubSpot coaching and consulting.

Thanks to George's strong personal brand and valuable content, more people came to him than he could help alone. He started hiring family members and contractors to assist with various aspects of the business.

"I looked around and realized I had three contractors also hanging around on a weekly basis to do things like web development and content strategy and writing," George recalls. "I said, shoot, you know what's funny is I'm not really a solopreneur anymore. I want to act like I am one, but we're literally sitting here running an agency and it's not being called an agency."

His agency is now called Sidekick Strategies, and a new chapter of his entrepreneurial journey has begun.

Facing the prospect of scaling further, he realized that he needed to have a closer look at the way his business operates. There were some problems to fix there.

The Challenges That Made George Focus on Improving Process and Getting More Out of ClickUp

As George's business grew, he realized that his current processes weren't sustainable.

His team was facing a range of challenges:

  • Their ClickUp was disorganized, and not being used for its intended purpose. "ClickUp was such a mess that many times I would just ignore it and I would be living my project management out of my email and my Slack and just the 'fly by the seat of my pants' conversations I was having with clients."

  • Lack of processes—their operations weren't fit to support a growing client load. "When you have one, two, three clients, you can kind of fly by the seat of your pants. But when you get into the five, six, eight, 10, 12 monthly retainer clients flying by the seat of your pants becomes painful. I mean, really painful and really messy."

  • There was no clear way to track work completed or provide client updates. "There was no real way to track what I had done and do a weekly recap and be able to send the clients: 'here's what we worked on this week.'"

  • It was difficult to delegate and bring team members up to speed due to lack of documented processes. "As soon as I tried to tag somebody else in—my HubSpot implementation specialist, or a developer on contract—then I had no foundation to stand on. I'm like, shoot, how do I download the things in my brain and what I've done and actually bring them up to speed?"

Without solving these challenges, George would continue to be stuck working in the business, unable to properly scale it.

He decided to seek support.


Finding a Partner in ZenPilot

Having known ZenPilot's founders, Gray and Andrew, for years, George knew exactly who to turn to for help.

"I pay attention to good humans and I try to surround myself with good humans," he says. "And so when I found myself in this transition point of going from solopreneur, going into an agency, and looking at my ClickUp and going, whoo, this is one big issue right here...

Immediately my brain went to, you know what? But I know the cats that could help me out of this. I know the people to tag in and the conversations to have."

George reached out to ZenPilot and embarked on our Blueprint process to optimize his agency's operations.

As part of the Blueprint, we laid out everything George and his team should include in their ClickUp workspace: the hierarchy of spaces, folders, lists, views, dashboards, automations, custom fields—all of it. We also provided training for the whole team to be able to run and maintain this system day to day.

How George and Sidekick Strategies Benefitted from the ZenPilot Blueprint

For George and his team, the ZenPilot Blueprint was a game-changer, and just what they needed at the time.

"I'm not joking: at that moment in time, in a place where we were ready to blow it up and rebuild, it was the roadmap to our future success."

Here's what George and Sidekick Strategies gained from working with ZenPilot:

  • Gained a clear roadmap for optimizing agency operations and efficiency. "It was insight into what it could be," George explains. "It was a roadmap in how to actually get started down the golden path, if you will, the yellow brick road to get to Oz, this place that we dreamt of and wanted to get back to this sweet home of being able to be optimized and efficient."

  • Received a customized blueprint and a plan to move forward with it, tailored to his agency's unique needs and goals. "It was a holistic journey and micro steps to take along the way."

  • Implemented systems that provided clarity for the team on project statuses and enabled more informative communication with clients, based on data from ClickUp. "We actually started doing a weekly recap where we send an email every Friday afternoon with all of the work that we've actually done for them for that week. We actually started inviting clients into their designated areas so that they could see the work in the moment if they wanted or create tasks for us there instead of asking us to do it in Slack or email."

  • Discovered newfound motivation and a fresh mindset around tracking time, which provided valuable data to inform pricing decisions. "We even started tracking time, which is crazy talk when you're talking about a person who comes from that solopreneur world." George reassured his team that the purpose of time tracking was not to micromanage their work, but rather to gain insights for the future. "We're simply tracking the time because in the future we need to know what we should be charging people to do the things that we're going to do for them. And what's funny is that was a totally freeing thing to people who weren't used to tracking time, but they knew the reason why. So we got a 'why', we got alignment."

Related: ClickUp Time Tracking Best Practices

  • Gained confidence in having a solid operational foundation—including being able to present where the team's time for a client is going if that's ever requested. "We are able to stand firm on 'this is the stuff that we've done'. Even though again, we never really had clients that were penny pinching us or asking if we use the hours because they're happy clients. But we still had this reassurance, this understanding, this belief that we have a system under us that if we were asked, if we got to that moment in time, we'd be good to go because yes, we are documenting what we're doing."

  • Gathered momentum to do more work in ClickUp and get better at it. "The interesting thing for me is that once you start down the path, once you've created one space with the folders that you need and the list that you need and you've done this customization, it's a lot easier to keep it going. It's almost like this snowball effect. Once it's in place, the next new client, it's net new super easy. So that to me was surprising like, oh wow, it doesn't always have to be a struggle. It actually gets easier along the way."

  • Received expert guidance and support from a partner truly invested in their agency's success. "[ZenPilot] fundamentally care. They care about your success. They're not just somebody they're trying to like do a thing in exchange for dollars. Like you can just tell that they're passionate about your future success."


Choosing to Self-Implement the Blueprint

While ZenPilot offered to implement the blueprint for him, George chose to take a hands-on approach and do much of the work himself. "I could have gone through this whole process and not done any work at all," he says. "I could have said, hey, here's my wallet. Here's my checkbook. Where do I deposit the money? And I could have had somebody just do it all for us."

But George wanted to deeply understand the system he was building. "I'm a big believer in going through the messy middle so that you understand like what it is that you've built, what's there, you understand how to use it, how to teach your team how to use it."

George did mention that he's likely to come back to ZenPilot for additional support in the future though, particularly in the area of automations.

Future Plans: Automating ClickUp and HubSpot with ZenPilot

The one piece George hasn't fully implemented yet is the automation between ClickUp and HubSpot.

"Doing it with ClickUp and HubSpot seems to be just this very unique beast to me," he admits. "And I'm like, I know I need this. I know I want this. I went and actually tried to take a swing at it a couple of times, but I keep not getting the results that I want."

George recognizes this is an area where leaning on ZenPilot's expertise would be valuable.

"If you know you want those platforms talking together, then keep ZenPilot along for the flight. And I'm sure that in the two or three times that I've gone to bat to try to do that automation and connecting those two platforms, ZenPilot team probably could have done it in half the time and it would already be in place."

Indeed, if integrating and synchronizing ClickUp and HubSpot is what you're after, we've solved this challenge for hundreds of agencies. To get started, check out Jeff's demo of what's possible with ClickUp + HubSpot here:

If you're ready to talk about your ClickUp setup and integrations to find the right solutions, book a consultation call here.

George's Advice for Those Considering ZenPilot

For those on the fence about working with ZenPilot, George shared two pieces of advice:

"So if you're on the fence, there's probably a couple reasons why you're on the fence.

One, you're curious about the value that they'll actually bring to your life.

My suggestion for that would be get that out of your head.

You're going to get the value that you need. They're going to get you over the hurdles that you're having. They're going to help your agency or business optimize itself as far as processes and the things that you need to do."

The other piece of advice was about how ZenPilot makes it possible to take gradual steps, proceeding from the Blueprint further into implementation and a ZenPilot subscription. This helps control the costs of the engagement if you're on a tight budget.

"The other side of this is you might be worried about the money that you have to spend to do the thing.

And what I love about ZenPilot is the fact that I can choose to do this in layers, right?

For so many companies, that's not the case. So many companies, it's like, yeah, we can build that thing for you for $152,000.

And then you can sit back and hope that it works.

That is not this case. That is not what ZenPilot has built or what they're delivering."

He also explained that getting ZenPilot's support is like an investment.

"Think of it maybe as the seed money to get that first initial part, at least make that investment to take the seed step, because then you'll start to see the initial value.

And once you see the initial value, once you start to make that initial move, then everything else mentally will fall in line to what it's worth or not worth for you to continue to move forward and fix the things that need to be fixed.

And so again, the value, it's there. Don't worry about it.

The finances, figure out a way to make it work."

Always happy to hear endorsements like this!

Ready to Level Up Your Agency Operations Like George Did?

George's story illustrates the power of investing in your agency's operations and partnering with experts like ZenPilot to guide you.

If you're ready to take your agency to the next level, consider booking a call with us.

As George says, "Believe in yourself and realize that you can probably achieve things that you don't yet believe that you can achieve. And the way that you're going to achieve those is by picking the right people to have in your corner as you step into the ring of life. And I'll just say for us, ZenPilot was definitely a set of those folks that we needed in our corner as we move forward in our agency life."

Don't let chaotic operations and disorganized project management hold you back.

Let's book a call together and have a look at the way your business is running—to find and fix the inefficiencies that are holding back your team and your profits.

Thanks for tuning in to George's story. For more ZenPilot stories and guides, go ahead and add me on LinkedIn to stay in touch—and I'll see you in the next one!

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