Chris Cunningham believes that as AI content proliferates, audiences will increasingly crave raw, real, human connection. He argues that audiences can sense AI-generated scripts and that investing in genuine human writing and unpolished production will become a significant competitive advantage.
While trying to scale impressions, ClickUp increased its posting frequency from once to twice a day. Counterintuitively, engagement and views went down noticeably. This suggests there is a content saturation point where audiences feel overwhelmed, proving more volume is not always better.
The social team actively monitors for high-profile followers. After discovering the COO of McDonald's followed their comedy account, they created a custom video DM from one of their actors to initiate a sales conversation. This tactic transforms passive social engagement into an active sales signal.
The team focuses its creative energy on just two core formats: short-form video (TikTok/Reels) and LinkedIn thought leadership. However, they repurpose and distribute this content across 35 different accounts and platforms, maximizing reach without stretching creative resources thin.
ClickUp treats social content creation like a TV show. On Mondays, a "writer's room" pitches and votes on ideas. Scripts are finalized Tuesday, followed by a check-in Wednesday. Every Thursday, they shoot a batch of 12-15 videos, ensuring a consistent and high-quality content pipeline.
Instead of pursuing established influencers, ClickUp's social team actively seeks out creators with just a few thousand followers but at least one viral video. This signals raw talent. These creators are often affordable, eager for brand partnerships, and provide an authentic, unpolished style.
Before publishing, ClickUp tests three variations of every video in "Trial Reels." This allows them to identify the highest-performing hook and headline without affecting their main account's reach. This process has led to videos performing 100x better than the originally preferred version.
After their social media gained traction, competitors began trying to hire away ClickUp's contract creators. To retain this crucial talent, ClickUp brought them on as full-time employees, offering salaries, benefits, and vesting equity, treating them as integral to the marketing team's success.
ClickUp's Head of Social, Chris Cunningham, rejects any social post that doesn't make the audience feel an emotion, add value, or teach them something. This simple filter prevents the common B2B mistake of treating social media as just another channel for corporate announcements and ads.
To get authentic material, Chris Cunningham interviews people in his target audience, asking what they find funny about their jobs. He offers them a small gift, like edited clips from the call, in exchange for their time. This direct pipeline to the customer's mindset fuels their content engine.