Asana vs ClickUp – Pilothouse Case Study

Pilothouse Case Study

How Pilothouse transformed their business operations from scrappy to streamlined by moving from Asana to ClickUp

About Pilothouse 

Pilothouse is a digital agency that specializes in scaling direct to consumer brands through high output teamwork. From digital media buyers specializing in all traffic platforms, talented designers, brilliant funnel builders, to crafty copywriters, our team is built to surpass performance goals.

About Yvonne Heimann

Yvonne Heimann, CEO of Ask Yvi, helps digital entrepreneurs dramatically increase profits and reclaim lost time by teaching how to implement proven processes, systems, and automation.


The main reason most businesses fail besides the usual: cash flow problems, inadequate marketing initiatives, negligent customer service, and unsustainable growth, can be highly attributed to insufficient planning and strategy. In fact, a lot of these business-related issues would have been addressed or resolved if the business had invested its efforts in optimizing and streamlining business operations.

Now, most entrepreneurs can attest that running a business involves implementing countless layers of planning and strategy, but what are the key differences? 

  • Planning is future-oriented, but it takes assumptions. 

  • Strategy on the other hand comes from practical experiences and can be for short-term or long-term projects depending on circumstances as well. 

The difference between planning vs strategizing may seem subtle, but to put it in simpler terms, planning is equivalent to having all the steps, while strategy provides you with the best steps. 

One thing to remember though is that it requires a great deal of brain space to implement both, and with Yvonne Heimann’s experience of running an agency, she believes that the quality of tools in your roster plays a vital role in how well or how poorly you will execute your business plans. This means that the tools and strategies you’ve had at the beginning of your business may not necessarily work in your favor when you hit the 6-figure or 7-figure mark.

But it seems like a lot of businesses don’t survive long enough to hit beyond 5-figures, let alone thrive in the ever-shifting economy without up-leveling their business roadmap. 

According to data from the U.S. Bureau of Labor Statistics, “about 20% of U.S. companies fail within the first year. By the end of their fifth year, roughly 50% have faltered. After 10 years, only around a third of businesses have survived.”

So, how do you avoid these pitfalls? 

Beyond having a highly customizable tool like ClickUp to handle a company’s multiple projects and departments while being able to scale with your business, it’s important to have the right expert in your corner because they can significantly reduce the time, money, and effort required for company stakeholders to learn and apply best practices from the get-go.

This case study aims to provide insight on the stark benefits Pilothouse has achieved from adopting ClickUp in their workspace and working with Yvonne Heimann – a dedicated business efficiency consultant – to train their company ClickUp champions to further streamline and optimize their business operations.

The Challenges

when moving form Asana to ClickUP

Pilothouse Operations Manager, Megan Williams, recalled what it was like trying to transition from a basic project management tool Asana to ClickUp.  According to her, Asana seemed to work fine when the business was relatively small, but after significantly growing their workforce to 50+ people, Asana proved to be severely lacking in features that would otherwise make reporting and managing business operations more efficient.

After careful deliberation, Pilothouse found it highly necessary to unify their departments and teams by using one project management tool, so that they can grow their business more sustainably. They found ClickUp to be particularly impressive and were keen on taking advantage of key ClickUp features such as: custom views & dashboards to help measure their progress, robust integration and automation capabilities, and future feature updates.

Andrew Stern (Pilothouse CEO) started getting his department heads onboard this transition, but even though ClickUp proved to be useful and versatile enough to meet their business needs, he confessed that it was too big of a project for the company to handle without having a business efficiency expert onboard.

For this project, Pilothouse needed help with:

  • Helping onboard the rest of their workforce to use ClickUp.
  • Creating and implementing ClickUp business structures beyond just the basic features and applications.
  • Streamlining their communication flow. Prior to Yvonne’s participation, team updates were disorganized and it was difficult to get an overview in Asana of what’s going on with the projects since everyone preferred to use Slack for task communication
Asana vs ClickUp - Pilothouse Case Study pin

The Strategy

to efficiently move from Asana to ClickUp

Upon joining the Pilothouse Asana to ClickUp project, Yvonne has implemented the following strategies in order to help Pilothouse stakeholders become more confident and self-sufficient in their usage of ClickUp:

  1. Developed a ClickUp roadmap and business strategy tailor-fit to Pilothouse’s organizational needs.
  2. Provided several channels (1:1 sessions, private ClickUp Chat access, direct email correspondence) to encourage open communication, timely support, as well as improve client accountability and project success.
  3. Shared additional business resources via Ask Yvi website and dedicated YouTube channel.
ClickUp Training Space within ClickUp
Ask Yvi's interactive ClickUp Training now used by team Pilothouse

The Results

Pilothouse achived after moving to ClickUp

Pilothouse on implementing ClickUp to organize and unify their company efforts:

During their early adaptation of ClickUp, Pilothouse expressed that it was overwhelming to learn everything there is to know about the tool since it had so many features. Compared to Asana’s simpler yet limited capabilities, ClickUp structures felt a lot easier to mess up and could potentially create unwanted domino effects across the other departments.

“With Pilothouse on ClickUp, we’ve been living and breathing ClickUp, it’s been awesome! Really appreciate all your help and support during those early days getting it set up.” – Megan Williams

After several 1:1 sessions with Yvonne Heimann, Pilothouse has shared how well they were able to implement multiple ClickUp features across the board. This has helped them build a more concise project overview that makes identifying, collecting, and analyzing data so much easier. This also means that Pilothouse was finally able to unite their departments’ and teams’ efforts in one project management tool and have now begun tracking their progress more effectively.

Pilothouse needing a better business structure inside ClickUp:

“You came in with a really great onboarding strategy for us. You got us to speed with everything that we needed to do – educated us. Also, developed a roadmap with us that would suit our needs. I feel like that was the biggest turning point was when you mapped everything out. We could visualize what we were trying to build and the scope of it. You really just opened our eyes, “Like, whoa! This is a big project and this is what we need to build.” It was like giving us an architect’s layout of, “THIS is what we need to build!” Megan Williams said.

As a business owner herself, Yvonne Heimann, understands and respects the need for creating and implementing strategies that play well with her client’s strengths. Which is why when she partnered with Pilothouse she made sure that they were receiving only the necessary pieces so that they won’t be distracted and allow them to take full advantage of ClickUp as a project management tool.

Pilothouse becoming more self-sufficient with ClickUp use:

Yvonne is a business efficiency nerd and loves nothing more than to review the latest tech and share the industry’s top business efficiency tips on her YouTube channel. So, you can just imagine just how many resources she has at her disposal.

Most, if not all, of her previous clients can attest that one of the highlights of working with someone like Yvonne Heimann was that she pulls out all the stops in order to provide outstanding support.This is simply because it’s not Yvi’s goal to make clients like Pilothouse to be solely dependent on her. It was this exact mindset of hers that helped Pilothouse become more confident in how they use ClickUp in their business operations, having grown a team of 150+ in the process.

“We have this system now that’s inspired by our interactions with you and all the support that you gave us, and we internalized that in our company so that it’s built into a lot of the processes that we’ve developed since then.” – Megan Williams

Interested in working with Ask Yvi?!

3 thoughts on “Asana vs ClickUp – Pilothouse Case Study”

  1. Love this and I too am a huge efficiency and productivity fan. It’s just a shame that ClickUp focuses a lot on new features and not so much on stability. In the UK we have had no ClickUp for the last 90 minutes or more… and the status page thinks everything is fine. My team and I have been using CU for around two years and in almost every way, it IS the best. But when on a Monday morning the software stops you from doing work… it makes me reconsider…

    1. There seem to have been issues going around this morning… I had other tools that were struggling too ;(
      Yay, technology… Hope CLickUp is back up for you?

      1. Hey, thanks for the reply. It is back up now thankfully… yes technology – we can’t live with it, can’t live without it! 😉

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