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Founder conversationUnicorn $50m+

How Clickup Bootstrapped to $25m

... Then Decided to Go All In and Raise $530m to Take on Giants

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

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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

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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”

Early growth priorities

“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

“Clickup Revenue Growth: First $25m”

Organic traffic growth

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

Landing the first VC

“Landing First VC at $25m ARR”

Series A and scale

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

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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

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Slide text

Find a passage in the slides and open the original deck.

10 passages

ClickUp’s bootstrap and funding context

  1. 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. 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. Clickup Revenue Growth: First $25m

Organic-traffic growth

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

  2. ClickUp’s first SaaStr 2017, Silicon Valley

Landing the first venture investor

  1. Landing First VC at $25m ARR

Series A financing and scale ambitions

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

  2. Source: Latka interview with Zeb Evans (Clickup Founder)

Key lessons from ClickUp’s growth

  1. 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. September 2022 Chris Cunningham Founding Member of ClickUp