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How Clickup Bootstrapped to $25m

From a failed side product to bootstrapped growth: fast shipping, SEO-led acquisition and competitor research

Chris Cunningham · Clickup

Published September 1, 2022
About this resource

In 20 minutes, you’ll learn:

- How to ship as fast as possible

- Why your data should tell your story

- Keys to nailing growth acquisition

Format
Founder500 Austin 2022
Length
23 min video
Inside
9 key moments
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What you’ll learn

Chris Cunningham recounts ClickUp’s path from early side projects and a failed Snapchat-adjacent product to a bootstrapped project-management company. He explains rapid product shipping, customer responsiveness, SEO-led acquisition, competitive research, early revenue milestones, and the financing decisions that preceded larger venture rounds.

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Key moments

Find the ideas you need and go straight to the source.

Bootstrapping the product

“bootstrapped we bootstrap so here's the cool part so at this point we just lost memory and they all knew about memory and they were like you know what are you gonna do and at the time this is where click up came Zepp hated project management this wasn't new he hated jira hated osana hated Trello and we hated also that people would use different ones if you were you know a very new user you're using Trello if you're in marketing you probably use Asana if you're in development you he's jiren he was sick of jumping from platform to platform so he's like we're not going to do that we built what we called MCC”

Ship before the product feels perfect

“like that's against everything we heard like it's it's a bad release like it's not we're gonna have problems and we don't have a bug team it's just like five of us maybe at the time maybe six and he goes yeah I got it but the people know what we're trying to do we're trying to build fast I think they'll understand and they'll send us the bugs and we'll quickly fix them and I was like well I have an idea that's cool you know when they when they send it to us listen instead of saying hey I'm so sorry let's say hey you're awesome customer thank you for pointing out that bug we're so sorry I'm gonna give you three months for your click up and I'm gonna be right back in touch as soon as”

SEO through competitor research

“we're so much better than their product one is was work Zone and we just like why are there blogs ranking they're you know they're not that great they're ranking so what do we do I stalked the guy who I saw was writing Josh bilker was his name I don't mind saying it it's a guy named Josh bilker he worked for work Zone and he was putting it all out there and he was really crushing it for them they're ranking and they're ranking they're ranking so I hit him up and I was like what is it going to take man we need we need you to do this for us we need this I need the strategy I need to know what you did I need to understand it and we got them how did you get them so how”

Convertible-note strategy

“the math what's 2.5 into 5 in terms of in terms of percentage equity right so true or false him writing himself his own convertible note early days saved him a lot of dilution in the series a round true it's just I've never heard this strategy before so anytime I get nuggets like that I want you guys to know about it we never did either yeah I was gonna say I don't know if Chris can even talk about this but and I didn't even fully understand when Zeb said it so you should just go look up Zeb CEO click up on YouTube and my interview with him is the first one he breaks it down and he”

Winning enterprise credibility

“Hey we're running out of money again um and I'm the only sales rep so I really worked hard and uh at this deal Randstad I remember going back and forth and trying to make them feel as if we're fully prepared for them which to be honest at the time I don't think we were we had to hire a lot of people after this deal but long story short I closed the deal but afterwards the the sound is going crazy never had this much money come in so there's so sirens and you know everything going off and also they call back and I'm not doing a cell phone this is like you know early days I'm on a landline still so I don't know where to answer the call when they're calling back I think I'm going to lose this deal”

Over the next 20 minutes

“Ship it, as fast as possible”

Organic Traffic Growth in 5 Years

“Organic Traffic Growth in 5 Years”

Landing First VC at $25m ARR

“Landing First VC at $25m ARR”

Clickup Revenue Growth

“$35m Series A at $250m Value”

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Resource files

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  • How Clickup Bootstrapped to $25m - Slide Deck

About the speaker
Chris Cunningham

Chris Cunningham

Founding Member and Head of Social Marketing · Clickup

Chris Cunningham is Head of SocialMarketing and a founding member of ClickUp. He has previously served as VP of Business Development at Elevator Studio and Head of Business Development at Mango Technologies, Inc. After completing his undergraduate degree in marketing, Chris went on to become the youngest manager at Cvent.

Company revenue
$200M
Team size
1000

More founder interviews

Slide by slide

Each slide with a short explanation of what it shows. Open the slide text for its exact wording.

10 passages

ClickUp’s bootstrap and funding context

  1. Slide text

    Chris Cunningham Founding Member of Clickup How Clickup Bootstrapped to $25m Founder500, Sept 2022 … and Raised $530m to Take on Giants

The operating priorities for early growth

  1. A three-stage growth roadmap

    The talk groups its lessons around reaching the first $25 million in ARR, raising the first venture round, and scaling beyond $1B. The advice spans fast shipping, customer engagement, product presentation, data, sales-assisted growth, acquisition, and hiring leaders.

    Slide text

    Over the next 20 minutes: Ship it, as fast as possible I’m going to show you FIRST 25 MILLION ARR LANDING FIRST VC SCALING TO $1B+ Be scrappy Proactively engage customers Trust your customers to believe in you Invest early in your product’s look & feel Have your data tell your story Layer in sales-assisted motion Nail growth acquisition Don't fuck up the culture. Hire leaders.

The first $25m ARR journey

  1. Revenue climbed to $200 million

    The chart shows revenue rising from $0 in 2017 to $1,000,000 in 2018, $25,000,000 in 2019, $37,000,000 in 2020, $80,000,000 in 2021, and $200,000,000 in 2022. Growth accelerates after 2018.

    Slide text

    Clickup Revenue Growth: First $25m

Organic-traffic growth

  1. Organic traffic grew past one million

    The chart shows organic traffic increasing from 0 in 2017 to 1M+ in 2022, with the steepest gains in the later years. Its displayed endpoint is 1,109,957 visits per month.

    Slide text

    Organic Traffic Growth in 5 Years 0 in 2017 to 1M+ in 2022

  2. ClickUp’s first SaaStr

    A photo of four ClickUp team members at SaaStr in Silicon Valley in 2017 marks an early company milestone.

    Slide text

    ClickUp’s first SaaStr 2017, Silicon Valley

Landing the first venture investor

  1. Revenue growth preceded the first VC round

    The chart connects the $25m ARR milestone with ClickUp’s first venture funding stage, then shows revenue continuing upward from $25,000,000 in 2019 to $200,000,000 in 2022.

    Slide text

    Landing First VC at $25m ARR

Series A financing and scale ambitions

  1. ClickUp sold 14% in its Series A

    The slide pairs ClickUp’s product homepage with a $35m Series A at a $250m valuation and says the company sold 14% equity in 2020.

    Slide text

    Clickup Revenue Growth $35m Series A at $250m Value …. Sold 14% equity 2020

  2. Funding rounds raised larger amounts

    The table traces ClickUp funding from a $1M convertible note in 2017 and a $1.5M note at a $5M valuation in 2018 to a $35M Series A at $200M, a $100M Series B at $1B, and a $400M Series C at $4B. The round amounts and valuations increase over time.

    Slide text

    Source: Latka interview with Zeb Evans (Clickup Founder)

Key lessons from ClickUp’s growth

  1. Three stages frame the lessons

    The recap returns to the same three stages: reaching the first $25 million ARR, landing the first VC round, and scaling to $1B+. It repeats the practical themes of shipping quickly, engaging customers, improving the product, using data, adding sales support, acquiring customers, and hiring leaders.

    Slide text

    Over the last 20 minutes, I showed you: Ship it, as fast as possible FIRST 25 MILLION ARR LANDING FIRST VC SCALING TO $1B+ Be scrappy Proactively engage customers Trust your customers to believe in you Invest early in your product’s look & feel Have your data tell your story Layer in sales-assisted motion Nail growth acquisition Don't fuck up the culture. Hire leaders.

  2. Thank you from Chris Cunningham

    Chris Cunningham closes with a thank-you and identifies himself as a ClickUp founding member.

    Slide text

    September 2022 Chris Cunningham Founding Member of ClickUp