It’s 2025. Your feed is flooded with AI-generated carousels, copy-paste hooks, and cloned content. Metrics might say “reach is up,” but the humans behind the screen? They’ve checked out.
SaaS buyers today aren’t just prospects!
They’re people.
People who are numb to sameness. People who don’t want to be marketed at. People who want something that feels… real.
In a world optimised for algorithms, authenticity is now your greatest growth lever.
“AI gives you average. It takes everything that’s been done and spits out the safest version of it. But humans? Humans spark reactions. That’s what your audience is craving.”
— Chris Cunningham, Founding Member at ClickUp
Chris Cunningham Knows What Works (and What Doesn’t)
As a founding member of ClickUp, Chris Cunningham helped engineer one of the most successful organic content strategies in SaaS—achieving 200 million monthly impressions without ad spend.
His approach? Combine human creativity with AI efficiency. Keep it relatable, emotional, and real.
Forget the chase for virality—chase connection instead.
Whether you’re in marketing, growth, brand, or just trying to figure out how to keep up in an AI-saturated landscape, here are 5 takeaways you’ll want to bookmark.
1. AI Is a Tool — Not a Strategy
Chris isn’t anti-AI. In fact, he uses it daily — for research, repurposing, even cleaning up voice memos. But relying on AI to generate content from scratch? That’s where most teams go wrong.
“AI gives you the average answer. It’s useful — but it can’t feel. It can’t make someone stop scrolling.”
The takeaway? Start with something human. Use AI to sharpen it — not to replace your voice.
2. Your Audience Wants You
We’re all overfed on content. What we crave now is connection. Chris calls it “B2Human” — and it’s about bringing people, not just products, to the front of your brand.
🎬 His best-performing content? Unpolished videos, office skits, and moments where things didn’t go to plan.
Whether you’re in B2B SaaS or building a newsletter audience, the brands winning today are the ones that show up as people — not templates.
3. Set Public Goals — and Let People Watch You Chase Them
Chris made his mission to hit 200 million impressions part of the story. And people followed along — not because they cared about the number, but because they could see the work behind it.
“Some of my most viral posts were about failing to hit the goal. That’s what resonated.”
Try this:
- Choose one bold goal (personal or company-wide)
- Share it
- Update your audience regularly
It’s not about perfection. It’s about the journey.
4. Content Creation Shouldn’t Be a Solo Sport
Chris runs a “writer’s room” model: regular brainstorms, rough ideas, ABCD testing (A=Proven hit, B=Solid baseline, C=Trend test, D=Wild experiment). The goal? More reps, more range, less pressure for every post to be perfect.
💡 His favourite method? Voice-noting ideas while walking. Feed the transcript into AI, clean it up, and go.
Whether it’s your brand page or your CEO’s LinkedIn, ideation should be a team effort — not a one-person bottleneck.
5. Your Team Is Your Brand — So Put Them On Stage
ClickUp’s “HR guys” skits are a great example: recurring characters that humanise the brand and make it instantly recognisable. The lesson? Let your people show up online as themselves.
Chris’ team even rewards internal creators with “ClickBucks” — points they can spend on real perks.
Want your content to feel alive? Let your employees post in their voice. Encourage takeovers. Build a cast, not just a content calendar.
✅ When You Do It Right, Here’s What Happens:
- 200M+ organic impressions
- A pipeline of engaged followers
- More trust, more talent, more talk
The best part? People remember you — not just your product.
Final Thought: The Internet Doesn’t Need More Content. It Needs More You.
We’re entering an era where sameness is the biggest risk. AI can scale content — but only you can make it matter.
“If your content feels like everyone else’s, it is. The edge is being real.”
So take the walk. Record the thought. Hit publish.
Because the brands that win tomorrow will be the ones that feel human today.
📢 Next Up:
Join us on May 28th together with HiBoB for People-Driven SaaS Wins: The Data (and Stories) Back It Up — where we explore how HR leaders are becoming real revenue drivers.
👉 Register and find out more here
Want to see Chris’ playbook in action? Catch his session on replay here
