Staff & Training

The 5 things no one tells you about going through hyper-growth

Ryan Chan

I’ll first start this off by saying that I’ve actually been told all five of the following points many times. I’ve heard them in person, in blog posts, in conferences, and more. 

However, it has been difficult for me to conceptualize all of the advice until it’s all right there in front of me, or even until after it has already happened. 

I’ve been told that MY role as CEO will change, that prioritization will be paramount, and that scaling a company is difficult beyond belief. I’ll be the first to admit that it is hard for me to realize this is eactly what’s going on until someone stops me in the middle of the day and makes me think back to realize what has already happened. 

I often make the analogy to the team that we’re on a mission to summit Mt. Everest. We’re doing something previously seen as impossible: revolutionizing the maintenance industry. And it can seem daunting when you stare straight up into the sky with no clue how you’re going to get there. So instead, I take every step inch-by-inch and day-by-day, always with my eyes up towards the summit. 

One of the most important things to do on the ascent up to our own Mt. Everest is to look back and enjoy the view from time to time.

I had one of those moments last week: I turned back and saw just how far we’ve come. What I noticed from my view were a lot of beautiful changes.

To me, it was just another ordinary day. I helped onboard a few new employees, went to a few meetings, and discussed goals for our product that we’re excited to reach in 2020. 

To provide some context, our conversations previously revolved around ensuring we have product-market fit and building a minimum viable product. But this meeting was a little bit different. Instead, it was focused on maximizing the value we can bring to customers from our existing core product.

This brings me to point number one of the top five things that change as your company goes through hyper-growth.

Read all of my insights from the climb so far below:

1. Once you’ve found product-market fit, double down, and focus.

Folks often ask the question, “Well, how do you know when you’ve found product-market fit”? 

I had recently read an article by Y Combinator about product-market fit and how to define it.

They say, “You have reached product-market fit when you are overwhelmed with usage—usually to the point where you can’t even make major changes to your product because you are swamped just keeping it up and running”.

Last week during that conversation with our product team, I realized that we have something that resembles this.

Today, I’m fortunate to say that UpKeep has 3,000 paid customers, 30,000 businesses that rely on us, 200,000 users, millions of work orders created, and hundreds of companies signing up for UpKeep every single day. 

And to be clear, it hasn’t always been that way! Even when I look back, I’m astounded at how far we’ve come! 

We got here, not by focusing on fabricating artificial growth, but by listening to our customers, iterating, and improving inch-by-inch and day-by-day. 

It was never about growth hacking or PR, it was always all about listening to what our customers had to say and solving a specific pain point they were dealing with in their daily work lives.

I think we, as a team, can confidently say that we’ve achieved this artificial milestone of finding product-market fit. 

And now our goal, which has shifted from trying to find product-market fit, is to take the product that was seeded a few years back to bring maximum value to the industry. 

We’re also shifting on an adoption curve as well, moving from the innovators and early adopters into the early majority and beyond. 

2. But even once you’ve found product-market fit…don’t slow down.

What I’ve always said to the team is that the one thing that we have on our side as a startup is the ability to move quickly, iterate, and improve.

Sure, we don’t have more time, more resources, more capital, or more employees than some of the biggest competitors in the space. However, what we do have is a team that is driven towards being better every single day, and the ambition and tenacity to continue innovating and improving at a faster speed than anyone else in the space.

So to wrap this point up, it’s important to know when to double down and focus; but it is equally as important to continue to push the barriers of the impossible. 

3. Everyone’s role gets a little bit smaller… and that’s an amazing thing!!!

As a five-person team, all of us used to do everything from support to sales, marketing, and product. We’ve gone from a small team, to now what I consider a mid-sized team as we approach 100 employees with folks distributed around the world.

We are beginning to hire specialists instead of generalists in a few core parts of the business. Everyone’s role is becoming more specialized at what they excel at. 

But the important keynote here is that as our roles become more specialized, the IMPACT that each role now brings to business is amplified

Instead of doing product, sales, support, and marketing at a mediocre level, we now have functional specialists that will help us become extraordinary in each.

As we move into growth and scale mode now, as Jason Lemkin says, “the cavalry has come!”

We’ve hired some amazing folks that are 20 times better than me at sales, marketing, support, and product. I am excited for this change and for you all to flourish doing something beyond the stretch of my imagination. 

To become the very best that you can and the very best that exists.

4. As the business grows, WE all must grow with it.

As we’ve grown in size and scale, we’ve had the amazing opportunity to promote several folks because they’ve shown the ability to grow into a role. And I am so incredibly proud to see that. 

At the same time, we’ve also seen some folks leave.

We’re growing at an unnatural rate, one that many define as hyper-growth. It is 100% normal to feel uncomfortable and to be pushed beyond what you’ve previously done before, and even what your current role states.

As we go through this growth period, we will all be pushed to grow with the business.

Khalid Halim, Co-founder at, said: “the law of startup physics is that humans grow linearly, but companies grow exponentially.”.

While we here at UpKeep believe that this is true, what Halim doesn’t mention is that WE all have the ability to change the slope of that linear growth curve by learning and constantly getting better. 

So, instead of setting the expectation for each of our employees that, “UpKeep will outgrow you in roughly 18-24 months,” we will invest in pushing, growing, and learning at the rate which we believe YOU can take us to the summit of Mt. Everest and beyond.

So, to the UpKeep team, I’m excited for you all! We’ve got a big challenge ahead of us and I’m excited for what’s to come ahead.

But I am also 100% aware that I am a target for it too. If I don’t continue growing, adapting, and improving, I am susceptible. 

I work on this every single day and I can absolutely tell you that I’ve made many mistakes. I’ve felt defensive about change, I’ve been hesitant about the things that I’m uncomfortable with, and I, for sure, haven’t always been right.

But I am learning, and I am so appreciative of your support. Thank you for pushing me to get better every single day, for teaching me how to be a better leader, and for your patience as I go through this learning experience.

I remember this quote each time I’m pushed beyond what I believe is initially possible.

“Comfort is the enemy of growth” 


“Change is the catalyst of doing something extraordinary”.

5. A founder’s clarity of vision becomes more important than taking action.

Since day one, I have absolutely loved the full lifecycle and process. I used to talk to customers, get feedback, design a few prototypes, write code, release the feature, and begin demoing it to new prospects in the matter of a SINGLE day. 

Now, as we approach 100 employees, I see my role changing from taking action to setting the vision and creating an environment that has allowed and enabled each individual on the team to get us to where we are today.

I hope to further enable and empower all 100 people on our team to run at breakneck speeds and to revolutionize the maintenance industry — exactly 100x faster than I could have done by myself.

So, this is the last segue into the conclusion here. 

I write this article for 3 main purposes:

  1. To help explain my clarity of thought to our amazing UpKeep team.
  2. To remind myself and improve my own personal awareness, so I can continue to get better and improve.
  3. And lastly, to help other entrepreneurs who are going through a similar transition that we are going through here at UpKeep.

Thanks, everyone for reading!!! 

I would love your comments and feedback!


-Ryan Chan, CEO and Founder at UpKeep

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