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Zeb Evans on ClickUp’s Vision, Traction, Roadmap, & Pricing

Gray MacKenzie
Gray MacKenzie is a true operations nerd who has spent the past decade helping hundreds of agencies build more productive, profitable, and healthy teams by solving the core issues plaguing their project management.

To chat with Gray and have ZenPilot lead your team through the last project management implementation you'll ever need, schedule a quick call here.

It’s rare to speak with a podcast guest who has had multiple near-death encounters.

We’ll come back to that, but for now, keep in mind that Zeb Evans is not your typical SaaS CEO.

I first met Zeb back in early 2018.

We’d been trying out ClickUp since late 2017, and we couldn’t believe their consistent product development velocity.

Between that velocity and their vision for the platform, Andrew (my business partner) and I decided to double down on ClickUp, first for ourselves. Then as the core platform, we helped agencies implement as we streamlined their operations.

That early bet on ClickUp has paid off in spades, as they’ve rapidly emerged as a major force in the project management space.

That rapid emergence in a crowded category is atypical, but so is ClickUp’s origin story (and founder).

Fueled by his most recent of 4 near-death experiences, Zeb moved to Silicon Valley in 2016.

He’d just exited a prior company and had plans to work on an exciting new startup venture along with a few of his co-workers from their previous workplace. However, before they got to work on building a better Craigslist, they needed to finish up an internal project that would help them better manage their work.

You can guess where this story is leading…

That internal project turned into ClickUp was shared with others and kept gaining traction.

Progress Over Perfection

In a world where Apple launches new products quarterly, Zoom pushes a new upgrade when major infrastructure flaws are publicized, and Slack’s most talked about update was their logo, I had to ask Zeb the obvious question:

“How does ClickUp ship at least 1 new feature every single week?”

His answer was simply ClickUp’s core mantra: “Progress over perfection.”

It’s not that perfect is impossible. On the contrary, Zeb believes that “perfection is possible, it’s just not possible right now.”

At this point in ClickUp’s trajectory, they’ve chosen to prioritize rapidly building and launching new and improved features and functionality.

While I don’t believe this approach is correct for every company (I’m ok with Stripe, QBO, and other companies that manage sensitive financial data taking a slower, more tedious path to deploying new features), I continue to love this about ClickUp.

It’s amazing to watch new features or improvements move through the pipeline. A welcome change from the pace of many SaaS roadmaps!

Leading ClickUp’s Product Roadmap

I’ve been told it was Shakespeare who first coined the phrase that “your greatest strength begets your greatest weakness.”

Regardless, that truism resonates with me.

ClickUp is no exception — the greatest strength of ClickUp is the incredible flexibility and versatility to handle almost any use case.

But we need to be clear about the flip side of that equation — it’s easy for new users to be overwhelmed by the flexibility and be paralyzed by the wide array of options, thus creating ClickUp’s greatest weakness.

With that in mind, I had to ask Zeb how he balances his own internal opinions on how users should do their work vs. listening to user feedback and building based on consumer demand. Especially given the development velocity where ClickUp is consistently pushing new features every Friday evening.

ClickUp actually has an elegant solution for this: ClickApps.

As Zeb explains, if a feature is requested and more than 20% of users will use it, ClickUp is likely to build it at some point. At their core, they want to remain a flexible platform where users can work in the style that best fits their preferences. But just because a feature has been built does not mean that everyone should be forced to deal with it in their daily interactions.

Instead of pushing every new feature into the platform, many of those features are built as ClickApps. As a result, they’re off by default, and the users who want to take advantage of those features can toggle them on in their Workspace settings.

The ClickApp solution is a great way to address the potential overwhelm for new users and has helped user adoption.

Secret Internal ClickUp vs. Public ClickUp

It’s not uncommon for other software platforms to test new features internally or in small betas for months before launching.

With a culture of shipping new features to production weekly, you would think that the difference between the public version and the version of ClickUp that ClickUp themselves use internally would be much less pronounced.

As it turns out, there’s still a gap between what the public sees and what ClickUp is running in their staging environment. One of the big distinctions is that ClickUp is running their own internal CRM that may eventually be released publicly 👀

Choosing ClickUp’s Pricing Model

We’ve worked with quite a few agencies who’ve saved 5K+ in annual software fees by switching to ClickUp.

For example, a team of 30 switching from Asana’s Business Plan to ClickUp’s Business Plan will save $5,760 annually (assuming both plans would have been paid annually; pricing accurate as of September 2020).

This begs the question around ClickUp’s monetization model.

Is it an early-stage market share play? Or are they generally happy with their monetization strategy?

Zeb’s answer here was firm, which was encouraging to hear from a consumer perspective. ClickUp will continue to be competitive and generous with their pricing, and if you’re considering adopting ClickUp, I definitely recommend listening to what Zeb shared here.

I’ve heard many comments about ClickUp’s “Let’s Make a Deal” note on their pricing page. Zeb shares how the unusual promotions angle stems from his entrepreneurial past. He also tells the amazing story of their first promotion and how they grew MRR from a few thousand in monthly revenue to over 100K in MRR in about 4 days.

Follow Zeb & ClickUp’s Journey

You can follow along with Zeb’s journey leading ClickUp by signing up on

For onboarding resources, I’d recommend both their written documentation and videos.

And if you’re an agency thinking about switching to ClickUp or if you want a second set of eyes on your current setup, reach out and talk to us. We’ve helped over 1600 agencies streamline their systems, processes, and project management – we’d love to help you, too!

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