How ClickUp executives built a 36M-impression LinkedIn channel in 12 months with Uptown’s Thought Leadership Content

ClickUp had built one of B2B's biggest social media engines, but the people behind it barely showed up on LinkedIn.

ClickUp did not need to be taught how to make content people watch. Its marketing team runs a weekly writers room, shoots twelve to fifteen comedy videos every Thursday, publishes across thirty-five accounts, and generates 150 to 200 million impressions a month. Muse by Clios called it "the SNL of project management platforms." Chris Cunningham, ClickUp's founding sales rep and now Head of Influencer Marketing, helped build that machine.

But the brand's content engine had not translated into a consistent executive presence on LinkedIn.

In March 2025, Chris had about 17,000 followers, hundreds of hours of podcast interviews, a library of proven ideas, and no time to turn any of it into a dependable publishing system. His profile defaulted visitors to Connect instead of Follow and gave incoming attention no clear path to a call. The video-first instincts that worked for ClickUp's brand did not transfer cleanly either. On LinkedIn, text was outperforming video, and reposting content that had worked elsewhere produced little traction.

Founder and CEO Zeb Evans was an even harder case. Chris had spent two years trying to get him to post. Other leaders across the company had expertise worth sharing, but ClickUp had no repeatable way to extract their ideas, write in each executive's voice, move drafts through approval, and publish consistently without turning LinkedIn into another job.

ClickUp had already ruled out prominent content consultants who “won’t get in the weeds.” It needed a partner that could meet a world-class marketing team’s standards and turn its executives’ expertise into a consistent LinkedIn presence.

"I put so much focus into LinkedIn for the brand that I forgot about doing my own."

Uptown became ClickUp's executive LinkedIn writers room, starting with Chris, winning over the CEO in five weeks, and scaling the system across five leaders.

 Uptown already had credibility inside ClickUp. A year earlier, it had moved the company's webinars onto LinkedIn Live, where the first event drew 1,310 attendees against a 400-attendee average.

The content program began with Chris. On the launch call, Uptown rebuilt the conversion path on his profile by replacing Connect with Follow and surfacing a Book a Call button. It then took over the weekly work: finding ideas, writing, editing, publishing, and growing the right audience.

Three to five posts a week came from material Chris had already created, including podcast interviews, ClickUp videos, personal experience, and strong ideas that had never been adapted for LinkedIn. Uptown also sent 200 targeted connection requests a week to marketing leaders at large companies, building an audience aligned with the people Chris wanted to reach.

The account quickly developed a recognizable format. In the first month, Uptown introduced a two-voice dialogue between a Head of Marketing and a skeptical CEO. The format combined a provocative opening, an executive objection, evidence, and a plainspoken conclusion. It ran thirty-five times over eighteen months and became Chris's signature series. When an idea worked, Uptown did not retire it. The team refreshed the hook, updated the evidence, and ran it again.

Five weeks after launch, the work accomplished something Chris had been trying to do for two years. Zeb read the posts and signed up.

For the CEO account, Uptown replaced the blank-page problem with a short weekly interview. Zeb answered three or four questions in roughly ten minutes. Uptown turned the transcript into posts in his voice across four content pillars, coordinated feedback and approvals directly inside ClickUp, and handled the publishing.

The same operating system then expanded to President Gaurav Agarwal, Chief Financial Officer Dan Zhang, and Head of Content and Growth Mark Sommerville. Each executive participated at the cadence their schedule allowed, from three posts a week to one a month. Drafts lived in ClickUp Docs, approvals happened in ClickUp Chat, and the executives' job was reduced to sharing their expertise and approving the final version.

Uptown worked with ClickUp to:

• Turn existing interviews, videos, stories, and expertise into a consistent executive content pipeline
• Build a distinctive recurring format that became recognizable as Chris's own
• Grow the audience intentionally through targeted connections with senior marketing leaders
• Capture each executive's voice through short recorded conversations
• Coordinate writing, feedback, approvals, scheduling, and publishing inside ClickUp's existing workflow
• Expand the program from one profile to five members of ClickUp's executive and marketing team

"Some of these lines you put in for me were magical. That was spot on. I was like, this is kind of crazy."