Chris Cunningham: Mastering the Art of Adaptation as an In-House B2B Creator

Chris Cunningham clickup
READ TIME – 9 minutes

Chris has been building a personal brand that goes hand in hand with ClickUp’s, the company he works for.

He grew his audience to 198,000 people on LinkedIn, Twitter, Instagram, and TikTok, and continues to grow.

But before you read this article, open your Shopify and put the ClickUp playlist on.

It has good vibes and will make like this article about Chris even more.

Who is Chris Cunningham?

If I were to define Chris in two words I would say he’s a risk taker

He started working on Cvent turning down top notch companies to work with and became the youngest manager and the company grew from 200 to 2,000 employees and went public with the product.

Soon he left his stable job and went to work on a project with his friend Zeb Evans, and that media company they were working on made over 500K a month.

Later, together with Zeb, the founder and CEO of ClickUp moved to Silicon Valley despite advisors telling them the chances to succeed are low.

In a few hard years, they grew ClickUp and now their company is estimated at $4 billion.

Besides being one of the founding members, Chris is the Head of Social Marketing at ClickUp and he’s doing an amazing job in his unique style.

What is Chris Cunningham doing differently than other B2B creators?

Besides being a strategic professional and Head of Social Marketing, Chris is also an in-house creator because he constantly creates content for the company he works for.

He’s not afraid to be the face of the company and he constantly educates and connects with the audience on behalf of ClickUp on his social channels.

Let’s look at things from a deeper perspective:

  1. Chris is the face of the company
  2. Has a strong point of view about the industry
  3. He’s not selling the app

Chris is the face of the company

Chris is aligning his personal brand with ClickUp’s brand.

Using the same brand colors

Starting from the icon he uses for LinkedIn, Twitter, and TikTok. It has the same shade of blue you can find in ClickUp’s brand colors.

Plus, the covers he uses for his personal social media accounts are ClickUp covers. He constantly pushes the company’s brand forward.

In all the bio’s he mentions he is a founding member of ClickUp showing how proud to work there and be there from the start.

Even the educational content that he publish on his accounts has the company’s brand colors on the presentations.

Sharing company’s milestones

To align with ClickUp’s success, Chris shares the company’s milestones on his personal channel like this time when he wrote about how they bootstrapped the company from $0 to $20 million due to deep product market fit.

Then he shares a ClickUp branded carousel about how they did it.

Using storytelling to humanize ClickUp

Chris also uses storytelling to connect with his audience to the company, sharing bits of ClickUp’s journey humanizing the brand.

In this LinkedIn post he talks about how he and Zeb picked a headquarter for their company in Silicon Valley and why they think it was the right place.

Ensures positive company culture

He impacts the company culture sharing insights from his and Zeb’s discussions talking about Zeb’s promises to him and how he kept all of them.

In this genuine way he shows that the company is based on trust and honesty.

He’s also sharing the company’s values. He creates videos about them and shares them on his social accounts.

Reshares ClickUp’s posts

Because he is so connected to the ClickUp brand, he constantly shares ClickUp’s content on his personal channels showing what they do and how they constantly improve their product.

Has a strong point of view about the industry

Chris Cunningham’s strong point of view in the industry, particularly in marketing and startups, is evident through everything he does online and in person.

And his competitive and leadership attitude shines through his approach to problem-solving.

To give you an example, take a look at this video where he discusses how he sees problems and wants to be better than with competitors.

Chris likes to make short videos about different conferences showing his and ClickUp’s audience what’s going on there.

Not just that, but he actively participates in industry events, further establishing himself as a thought leader. 

For example, he shares content about the events he joins, such as Inbound23, showcasing his commitment to staying at the forefront of industry trends.

He is also invited to speak at prestigious events, including The Next Web Conference in Amsterdam. 

This is how he shares ClickUp’s success story live and provides valuable insights into marketing, startups, SaaS industry connecting more people to him and ClickUp.

He’s not just invited as a speaker to different live events, but he is also invited to podcasts and webinars.

There he also shares valuable insights about the industry with wider audiences.

Due to all of these webinars and events, it’s safe to say he constantly stays informed about what happens in the industry like the time top tech leaders talked about shutting the AI down and made a video about it.

We can also see him as an educator because he shares content about marketing, about different strategies that other brands applied or didn’t, and how brands managed to succeed.

One time he developed a comprehensive carousel detailing his experience spending over $10 million on marketing campaigns and outlining eight marketing strategies he would implement again if starting from scratch.

He’s not selling the app (entertain, educate and inform)

What differentiates Chris from others is his approach to content creation because he adapts it to suit the dynamics of each social media platform.

On TikTok, Chris focuses on entertainment and engagement.

He captures the audience’s attention with creative and well-edited content, leaving a lasting impression on his followers.

He mixes content about himself and his work life balance with short form videos about ClickUp.

A video where he presents things from his life is this one below where he talks about the decisions he made that helped him be the person he is today.

He starts the video in a catchy way saying that he’s going to talk about “the mistakes” he made in his life till 34 years old.


Shit its my birthday. Here are the top 4 devistating mistakes I made in the last 34 years that ill never make again.

♬ original sound – Cunningham

What’s interesting about his personality besides being a risk taker is how he sees everything like an opportunity to learn something new.

He made a video about the fact that he won’t be able to talk for ten days due to a surgery, but sees that as a chance to learn to listen to people more saying he’s really excited about this.


Dr said I cant talk for 10 days. So im gonna find a way to still create content for the next 10 days without my voice. #NoTalk10Days

♬ original sound – Cunningham

Interestingly, most of his TikTok videos are used on Instagram as well as reels and, here he has managed to reach a massive audience of 126.000 followers.

Twitter/X, being a platform known for quick updates and real-time information, becomes Chris’s space for delivering concise and informative content.

He informs his followers about current trends and discussions around AI, technology, marketing, and businesses.

One of his recent tweets is about workers’ fear that AI will replace them and talks about an interview with Airbnb’s Co-founder Brian Chesky.

His deep interest in AI is a recurrent theme in his tweets talking about AI tools creators, marketers, and founders should know about to succeed in their businesses.

In some posts he mentions ClickUp as an AI tool for optimizing daily work processes.

And he started to engage in conversations with his audience.

LinkedIn serves as Chris’s platform for education and thought leadership by sharing valuable insights about the industry and how different businesses have become successful.

So we can say that this adaptive content strategy showcases Chris’s versatility and demonstrates a good understanding of the distinct nature of each social media platform.

He knows how to maximize his impact, ensure a genuine and effective connection across diverse communities, and connect them to ClickUp.

ClickUp’s different strategy

What ClickUp has done differently is to invest in building in-house creators.

But why?

It was their strategic initiative to create more distribution channels. Plus, in-house creators bring several key advantages to the table.

Advantages of building in-house creators

They know the company’s brand identity and values, and most importantly they know ClickUp inside out.

This lets them create content that aligns with the company’s target audience and they maintain a cohesive brand message while directly communicating with the audience.

Moreover, in-house creators can bring a unique way of communication.

Like Kenneth Harkness, ClickUp’s Creative Coordinator, who created an entire Spotify playlist for ClickUp with songs they’ve written for their integration, for work mood, and more.

KJ Harkness is the Founder of VLNZ LLC., a VA-based company that provides music and content production to businesses and artists.

He’s been friends with Chris and Zeb since college, and Chris invited him from time to time to write songs for ClickUp and now he’s a full time employee.

And they launched an album called “Work Flows” that after 2 months of release the album had almost 1 million streams across Spotify and Apple Music, according to Cunningham.

Moving further to why in-house creators are better, they’re also cost efficient.

External influencers or creators might bring their unique perspectives, but at higher costs, bringing their specific niche of audience, but in-house creators are more deeply integrated in ClickUp’s company culture.

Want proof that this is more efficient?

Melissa Rosenthal is ClickUp’s Chief Creative Officer and actively posts on her LinkedIn about marketing and Saas in general, she gets invited as a speaker to events around the globe, and her online presence brought her 25,024 followers on LinkedIn alone.

Not just that, but she has thousands of likes and comments on her posts, and reshares.

Take a look at this post about the C-suite that keeps their calendar hidden where she openly asked her audience to speak their mind. It has 3.497 likes, 1.224 comments, and 83 reposts.

Having a sense of ownership in the content creation process for ClickUp, brings their in-house creators more passion and dedication to their work. This results in creating higher quality and authentic content building trust with ClickUp’s audience.

Plus, another important thing that in-house creators bring to the table is that they are in for the long shot. As opposed to influencers with whom a company may only work for a project or two, in-house creators engage in long term strategic content aligned with the company’s goals.

The CEO can be a B2B creator as well, as we’ve previously seen with Nathan Barry from Convertkit.

Zeb, is also growing his audience on LinkedIn and Twitter and talks about entrepreneurship, Saas, and you guest it, ClickUp.

Not to mention the benefits of being an actual in-house creator

Besides the obvious, understanding the product, the audience, the needs, the strategies better, you’ll have a higher job stability.  

This stability provides in-house creators with a sense of security and the opportunity for long-term professional growth within the company.

You’ll also have higher opportunities for career development within the company. You can take on leadership roles, expand your skill set, and contribute to the growth of the overall content strategy.

What lessons can you learn from Chris?

Align your personal brand with the company’s brand

Chris perfectly aligned his personal brand with ClickUp’s on all his personal social channels.

He uses the same brand colors, talks about ClickUp’s company milestones, talks about his private discussions with the founder, and so on.

Having this consistency between personal brand and company brand creates a recognizable identity which makes it easier for the audience to associate you, the in-house creator with the company you work for.

And this tremendously helps to establish trust and loyalty.

Use storytelling when creating content

Chris effectively uses storytelling to humanize ClickUp which helps connect his audience on a deeper level. 

By creating posts about personal experiences, such as Chris’s talk with Zeb where his friend shared some promises about ClickUp , Chris made his content resonate with his audience emotionally.

This connection enhances engagement, as audiences are more likely to connect with individuals who share not just professional insights but also personal insights because it’s more relatable.

Have an adaptive content approach

Chris shows us the importance of adapting content to suit each social media platform. 

So learn to tailor the content to the strengths and characteristics of each platform, considering the preferences of your target audience. 

Whether it’s entertaining on TikTok, educating on LinkedIn, or informing on Twitter, as Chris does, an adaptive content strategy maximizes your impact across a broader audience.

Final Thoughts

I must say, I enjoyed writing about Chris because his attitude of “you can make it, embrace fear and do it, taking risks” is truly encouraging. This power of his beliefs helped him face all his challenges. 

As founders, creators, and marketers, we should definitely embrace his mindset because overcoming our fears will give us a profound sense of personal achievement.