People person from a small town. Working hard to better myself everyday and will take on every project I have time for.

Chris Cunningham

Head of Marketing: I'm fixing our attribution by asking customers how they found us.
CEO: No you're not. That's not scalable..

Head of Marketing: Neither is last click attribution... Dark social is 70% of our current pipeline and we're pretending it doesn't exist.

CEO: What are you on about... what's dark social?

Head of Marketing: Every untrackable share that actually drives decisions. Like screenshots shared in Slack, Discord or a text between two VPs.

CEO: We can't measure that... and we can't optimize what we can't measure.

Head of Marketing: We can't measure it because our attribution model is broken. Our tools only tell us "what did they click?". Instead we should just ask THEM "how did you actually find us?"

CEO: And people will just... tell us?

Head of Marketing: They already are. I added one question to our onboarding calls: "Walk me through how you discovered us."

Turns out our biggest deal this month came from a Reddit thread that got screenshot, shared in a private Discord, then forwarded to their team Slack.

CEO: Our attribution says "direct traffic."

Head of Marketing: Exactly my point.

CEO: The board wants dashboards.

Head of Marketing: The board wants revenue. I can show them a spreadsheet of "how we actually found you" from every customer. That's real attribution.

CEO: How do we scale this?

Head of Marketing: One question in every sales call that gets added to a field in the CRM. Actual insights that marketing can work off of.

CEO: If this doesn't work...

Head of Marketing: It's already working. We stopped tracking last-click nonsense and started listening. Turns out customers will tell you the truth if you just ask.

PS - Dark social drives more B2B pipeline than any channel you're tracking.

Thoughts?

I'm Chris Cunningham - I run social media at ClickUp.

Follow me for more actionable marketing tips & tricks.

Chris  Cunningham

li_at

JSESSIONID

Talks about #saas, #startup, #branding, #marketing, and #influencermarketing

Founding Member ClickUp / Marketing

Michelle Strom

When ClickUp launched, nobody wanted us. I was our first sales rep and nobody cared what I had to say. So I set a rule for myself...go for 50 no's before I quit.

I made call after call. Most people hung up, while others laughed. A few were polite but not interested.

Then I closed my first deal & that feeling was so sweet I'll never forget it.

I set the counter back to zero & went for 50 more no's.

But I never hit 50 again. I closed another one, then another, and the momentum built from there.

I took a lot of those early lessons from sales & still apply them to content/social media today.

I see the same patterns with content. Founders post 3 times, get no traction, and quit. They never make it to their first win because they aren't expecting all the "no's" or failed posts.

But content is the same game as sales. You're going to hear no most of the time and the algorithm will ignore you. Your first 20 posts will probably flop. Maybe even your first 100 posts.

That's not failure though...that's the process.

Set a number. 50 posts. 100 posts. Whatever keeps you going long enough to see what works.

Because the first win will feel so sweet that you'll want to keep going. You'll start to learn what your audience responds to. You'll build momentum, and eventually you'll stop guessing.

But you have to make it to that first win. Most people quit before post 15.

Thoughts?

It's Monday. Which means we're going to pitch 20 content ideas to create this week. Only 8 will survive. Here's exactly how it works (steal this framework):

I show up with 3 ideas that I usually find from tweets that went viral or something bizarre I saw over the weekend.

Like last week I saw a tweet asking "what would you do if the FBI showed up and you had 30 seconds to hide a thumb drive?" The replies were unhinged. That became a video.

Luke shows up with 3. Adam shows up with 3. Our guest writer - usually some comedian from the LA scene - shows up with 3-4 more.

We pitch them all, and then we vote blind. No one knows whose idea is whose.

The winners are whatever gets the most votes - pure democracy.

After we pick our 8-10 winners, I sort them into what I call the ABCD formula:

A = Stuff we know crushes. Like HR guys dancing. We'll remake 2-3 of these.
B = Concepts that worked elsewhere that we can steal and make our own.
C = Whatever trend is happening. Severance drops? We're making a Severance parody.
D = Complete wild card. Something so weird it might bomb or might get 100 million views.

By noon, we know exactly what we're shooting Thursday.

Tuesday we'll figure out props and locations.
Thursday we shoot all day.
Friday I color-code everything based on performance.

This system has generated over 1,000 videos & we've hit 200+ million monthly impressions with this strategy.

All because every Monday, a room full of comedians and actors who barely understand project management software vote on what makes them laugh.

Your content strategy probably took months to develop.

Ours takes 2 hours every Monday (and adapts to trends in real time).

Head of Marketing: We're done with the brand voice guide.
CEO: The 47-page document we spent $30K on? No way..
Head of Marketing: That's the one.

CEO: Why? It ensures consistency.

Head of Marketing: It ensures we sound like every other SaaS company in existence. I ran an experiment. Took our last 10 posts and 10 from our competitor. Removed logos. Our team couldn't tell the difference.

CEO: That's why we need guidelines.

Head of Marketing: Our customers don't want guidelines. They want to know who we actually are. I looked at every piece of feedback from last quarter. The word "generic" appeared 23 times.

CEO: So what's your plan?

Head of Marketing: Let the team sound like humans. Sarah in product has a sarcastic sense of humor. Let her write like that. Tom in sales tells incredible stories. Let him tell them.

CEO: We'll sound inconsistent. The brand team will hate this.

Head of Marketing: The brand team already agrees. They told me they're tired of writing "synergy" and "leverage" when they'd rather just say what we actually do.

CEO: Legal will have a field day.

Head of Marketing: Legal approved our last 5 posts that said "our competitors suck at onboarding." Got more positive replies than anything we've published in 6 months.

CEO: This could backfire.

Head of Marketing: You know what's backfiring? Our NPS dropped 12 points. Customers said we "lost our personality." We used to be scrappy. Now we sound like IBM.

CEO: One quarter.

Head of Marketing: When our engagement rate triples and customers start saying "this actually sounds like you guys," I want to burn that brand guide.

CEO: Deal.

P.S. - Nobody ever bought software because it "leveraged synergies." Stop using corporate jargon, and start telling stories that are actually authentic.

I'm Chris Cunningham - I run social media at ClickUp.

Follow me for marketing that sounds like it was written by a human.

I analyzed our last 1,000 videos at ClickUp. Here are 7 things that actually move the needle on our social media content:
(1) Instagram Trial Reels

Trial Reels are free A/B testing that nobody uses to test 3-5 different hooks. They don't show on your feed, so you can pick the winner for your "real" post. We tested 3 hooks - one got 13k views, another got 1M. That's a 77x difference.

(2) Actors cost less than your agency retainer

LA actors: $60-80k/year. They show up on time, take direction, and don't have ego. The social media gurus recycle the same 5 hooks everyone uses.

(3) Your social media "best practices" are why you're failing

I was told to always show the product, always use UTM links, make people argue in comments... I ignored all of it and now we generate 200M+ impressions/month now...the board loves it.

(4) Stop creating new content - recreate winners

Our HR guys dancing video hit 30M views. So we made finance guys dancing, then IT guys dancing, then Sales guys dancing. 100M+ views total that all stemmed from one winning idea.

(5) Weekly brainstorm meetings > Strategy decks

20 ideas go in every Monday, then 8-10 of the best ones survive after the team votes blindly. The winners get turned into content. This 2-hour meeting generates more pipeline than any strategy deck I've ever seen.

(6) Pattern interrupts that actually work

Opening a banana backwards, someone bursting out of a car trunk, literally circling someone's back when saying "circling back." Subtle confusion from visuals works just as well (if not better) than the words you actually say.

(7) Color-code your best/worst creative

Green = 20k+ views (recreate it)
Yellow = 5-20k (tweak the hook)
Red = under 5k (don't reuse)

This system turned random viral hits into predictable viral hits.

What else would you add to the list?

POV: You thought making a rap about ClickUp was a good marketing decision...

It was.

We spent $50K on a bunch of expensive Sony cameras at ClickUp, but our iPhone videos get 10x more views. This is just the tip of the iceberg on a bigger trend I'm noticing...

People scroll past overproduced content now because it signals corporate ad, not authentic insight. Raw content from a phone feels like you're letting them in behind the scenes, and that's what makes them stop.

I see founders all the time that wait to start creating content because they think they need the perfect setup.

They're shopping for cameras, researching lighting setups, and building out entire studios when they haven't even posted their first video yet.

It's absolutely insane because your audience doesn't care about your gear. Especially when you don't have an audience to begin with.

Whether you're just getting started, or you've been in marketing for 30+ years it's good to be reminded of the basics that actually matter.

The hook matters. The message matters. Authenticity matters. Production quality? Dead last.

tldr; If you can't make good content on your iPhone, your $5K camera won't fix that.

Set your phone up. Hit record. Say something worth hearing. Rinse & Repeat until it works. That's it.

That's the whole playbook.

Agree?

I’ve generated more than 1.8 BILLION views for ClickUp in the last year but NOTHING compares to my first taste of virality - when I FAKED winning the lottery in 2012.

Yep. Long before B2B memes, actors, and 300M-impression goals… I was a broke college kid at Virginia Tech with three friends, Photoshop, and a dumb idea that fooled the entire country.

Here’s what happened:
The Mega Millions jackpot was $640M.

Less than an hour after the drawing, with the help of Zeb Evans ClickUp CEO, I tweeted a Photoshopped “winning” ticket with nothing but:

👉 “My life has forever changed.”
That was it and the internet lost its mind.

Within hours I was trending globally. Journalists, fans, haters - even Good Morning America and CNN - flooded in.

People I’d never met proposed to me.
The DMs were… unhinged. Let’s just say some invitations were not PG-13.
My parents had to unplug their home phone because my small hometown Martinsville was convinced their son had just become a millionaire.

Meanwhile… we were goofing around in our apartment debating:
“Should we go out drinking tonight… or should we fool the world again?”

We chose the world - and it worked. Our entire goal with this prank was to get onto Comedy Central’s Tosh.0 - and it nearly worked.

That moment taught me my first real lesson in content:
When you understand attention, the world reacts. When you manufacture a moment, the world amplifies. 

When you break the pattern, people stop scrolling.

Fast forward to today, and the same principles drive everything we do at ClickUp:
• Make people feel something.
• Break the “B2B is boring” mindset.
• Be the cool brand in a boring industry.
• Study people harder than you study algorithms.

Because virality isn’t luck - it’s psychology, timing, and understanding humans.

Last click attribution misses 95% of the story which is why your LinkedIn campaigns are probably performing 10x better than your dashboard shows. 

We solved this...By using Dreamdata to connect pipeline data directly to LinkedIn. Now our algorithm optimizes for revenue, not vanity metrics.

Want the same visibility? Comment "DREAM" below.

I've written 4,000+ posts for ClickUp's social accounts, and cut my teeth on more failed posts than I'd like to admit. Now, every post I make needs to do at least 1 of these 3 things, or I don't post it at all (share this with your team):

Somewhere along the line B2B marketing got so far away from B2C marketing that it's become out of tune with what actually works on human beings.

That gives the saavy B2B marketer a huge opportunity to fill this gap for their audience. Try one of these angles out for your next post:

(1) Make your audience FEEL something

Anger, hope, or relief. The feeling "that someone finally gets it" is what I'm going for here.

We posted about pretending to understand what your boss said in that meeting while frantically DMing your coworker for translation. It blew up because we said what everyone was thinking but nobody talks about.

(2) TEACH them something they can use today

I'm talking about something they can implement before their 3pm meeting. That's the good stuff people will come back for more of.

Not just another framework or theory.

(3) ENTERTAIN them

Yeah, even in B2B you can entertain your audience.

We had our actors dress up as different departments and dance to old songs. Dumb? Maybe. But it got more than 30 million views while our product demos got 800.

Team leads and VPs are real people who doom-scroll at midnight & laugh at the same stuff everyone else does. Lean into that while the rest of the market is clueless.

If your next post doesn't do at least one of these, edit it until it does.

1 out of 3? Solid post.
2 out of 3? Now you're onto something.
3 out of 3? This is where things compound.

Thoughts?

PS - Let me know why you think B2B marketing has become so...boring. When did things first start to go wrong?

I'm Chris Cunningham - I run social media at ClickUp.

Follow me for more actionable marketing tips & tricks.

Every week I interview project managers using tools like ClickUp to learn about the content they actually watch. Their answers almost never match what "thought leaders" tell you to post about. Here's 3 questions you can steal to figure out what content your ICP wants you to create:

Most marketers live in a bubble talking to other marketers… which is great if your ICP is marketers. But if you're selling to anyone else, you have to escape the echo chamber and figure out what they actually consume.

So I started interviewing actual users. Share these questions with your team:

(Question 1) What content do you actually watch?

They never say LinkedIn thought leadership content. They say comedy sketches, TikToks, and YouTube videos about literally anything except productivity hacks.

That's when I realized that after 10 hours of actual project management, they don't want more project management content. They want to decompress.

(Question 2) What's something cool you learned last week?

Not one person has ever mentioned a framework from a carousel. It's always some random thing that stuck because it was entertaining first, educational second.

This told me to stop leading with value props and start leading with entertainment.

(Question 3) What would genuinely help you?

They don't want another "5 tips" post. They want to feel seen. They want someone to acknowledge that work is absurd sometimes. They want to laugh at the same corporate buzzwords that drive them insane.

So we created exactly that. We started making content that makes them laugh about their reality instead of lecturing them about it.

Project Managers spend 8 hours a day in meetings about workflows and optimization. When they open their phone, they don't want more of that. They just want to chill for a second.

A lot of these execs you're trying to reach - they're still regular people & they like to laugh..

15 minutes talking to actual users taught me more than 3 years of marketing conferences.

You're guessing what your audience wants based on what other marketers tell you. I'm asking them directly and creating exactly that.

One of us is getting 100M views from dancing videos.

Maybe try asking your audience what they want instead of telling them what they need.

We doubled our content performance in 90 days at ClickUp using a color-coded system. Here's how it works so you can steal it (bookmark this for later):

Most teams create content, then move on and never analyze what actually worked.

At ClickUp, we test everything so we can double down on the winners and ditch the losers. Here's the exact process:

Step 1: Create content for at least a full week

Don't analyze results daily, you need to give yourself enough data to spot patterns.

Step 2: Put all your videos/posts into a table

Links in one column, impressions in another, likes, comments, and so on. 

We use ClickUp for this (and you should too!)

Step 3: Color code everything - keep it stupidly simple

Green = Winner. It performed well.
Yellow = Potential. Needs tweaking.
Red = Miss. Don't repeat this.

Step 4: Make decisions

Reds: Stop making this type of content.
Yellows: Change the hook or format, try again.
Greens: Remake it. Your audience already proved they like it.

Most marketing teams try reinventing the wheel every week. This allows you to have an ongoing system. Then when trends happen, you can hop on them without breaking your entire process.

When something works, double down on it. Make more versions of it.

Your greens show you what your audience wants so give them more of it.

Do this every week and your numbers will climb because you're learning what works instead of guessing.

In App analytics are great, but there is something to having all your channels + posts in a single location to analyze and share with your team. It makes things more accessible.

Thoughts?

The most interesting distribution channel in 2025 isn't TikTok or LinkedIn.

It's AI model training data.

Let me explain:

Warner Music Group just partnered with Suno.

They went from suing to partnering.

Why?

Because they realized something:

If AI models train on your content...

Your brand becomes part of AI's worldview.

When someone asks ChatGPT for music recommendations?

The models trained on Warner content will recommend Warner artists.

This is distribution at the infrastructure level.

Not on the platform.

IN the platform.

And most brands are still thinking about this wrong.

They're trying to block AI from their content.

When they should be negotiating to be OVER-represented.

Because here's what happens:

AI becomes the default discovery layer.

The brands in the training data win.

The brands blocking it become invisible.

Same pattern playing out in:

Recruiting (AI resume screeners)

Sales (AI research tools)

Marketing (AI content generators)

If AI can't learn about you...

It can't recommend you.

Are you optimizing to be AI-discoverable or AI-invisible?

Huge move from the Replit team, Fast Mode is a real step up - and I don't even code haha! 5x faster workflows, and it’s free to try. Highly recommend checking it out if you haven't yet.

Replit is free for the first time ever! 
  
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Poolside Ventures

Buyside M&A services and a Venture Studio for profitable companies with small teams

Founder & CEO

SaaS on the Beach

Exclusive retreat for successful SaaS founders

Dealfront

Buyside M&A Advisor

Chief Product Officer

B2B Go-to-Market platform with data and applications for sales and marketing teams.

VP of Product

Connected Product

Software development agency for B2B SaaS, specialized in email and calendar functionality.

Founder

ZoomInfo

Director of Product Management

Principal Product Manager at RingLead

FunnelFox

Engagement Platform for Sales and Customer Success

Ciuvo GmbH

Live price comparison software for webshops in 32 countries

Director Of Business Development

Gutscheinalm / Promo Kuponi

Coupons for Austrian and Russian webshops

Deloitte Nederland

Operational Excellence Consultant

StudentService Amsterdam

Co-Founder & CEO

Building profitable B2B software companies. 

Bringing together successful founders through SaaS on the Beach.

Vincent Jong

2025 has been incredible and I figured it's time for a reintroduction: Hi, I'm Vincent, and I help companies unlock the AI advantage 👋  Here's how:

1. As Founding Partner at Second Horizon, I partner with executive teams to drive AI adoption and workforce transformation.

While many companies struggle with failed pilots, we guide them on where and how to start delivering real value. This is strategic consulting, we don't handle implementation (but we can connect you with experts who do).

2. To stay sharp on AI trends, I run Poolside Ventures, a venture studio that builds AI-first companies with solo teams.

Last month, we launched Meet.bot, and January brings our next big release. I share learnings from these ventures here on LinkedIn, and they fuel our work at Second Horizon.

3. I'm also the organizer of SaaS on the Beach, an invite-only retreat for SaaS founders with 7-8 figure revenue. Think of it as my escalated passion project 🙂 

We bring 60 founders to Barcelona for two days to step back, connect with peers, and learn from each other. I'm sure AI will come up, but the real magic is in those personal connections.

So, that's the updated me. Going forward, I'll focus on AI strategy and AI in the workforce, sharing demos and real-world examples whenever possible.

Second Horizon is my main brand now, and I'll highlight our projects from that lens. Oh, and I might revive the podcast next year with a focus on AI. More on that after the holidays 🎆

Unlocking the AI advantage for companies | AI‑first founder | Host at SaaS on the Beach

Calling every “exit” a success is absurd. Pitchbook shows that more than 70% of VC-backed exits in recent years were worth less than the money put in. That’s not success, that’s damage control.

And not all exits are equal. An acquihire of a tiny 50k-revenue product isn’t the same as selling a 1000-people company. Some exits happen because there was no way forward, others because the opportunity was genuinely great. We pretend they’re all the same story.

Building a company is brutally hard. I’ve failed myself in the past and it taught me what actually matters: profitability, resilience, and how long a business can run without outside capital. Why can’t we be excited about those things?

Not every founder gets the chance to hear directly from people who have exited their businesses. At SaaS on the Beach 2026, we’ll change that, thanks to our second main sponsor, L40º Tech M&A.

Over the past year, we’ve shared dinners and conversations with them, like this photo last week at our Tekpon AI Summit dinner. Next year, we’re bringing these discussions to a bigger stage. 

As part of our 2-day program, we’ll host an intimate panel with founders who have successfully exited, sharing lessons you won’t find in any blog post.

Seats are limited and invite-only. To claim your spot, head to the SaaS on the Beach website and apply. We're assigning tickets every month so don't wait too long!

Building products has never been easier. Selling them has never been harder.
But what if building became your new unfair advantage in selling? 💡 

Customer acquisition costs are up. Conversion rates are down. The old playbooks aren’t working.

The good news is that today’s AI tools let us ship functionality faster than ever and that opens up new distribution paths. 😲  

And I’m not talking about product-led growth (yet). I mean building core product functionality designed to attract customers.

Take integrations. There is zero excuse anymore not to integrate with every tool your customers rely on, it’s become unbelievably easy.

At Meet.bot, we leaned into this from day one:
- Launched with integrations into the major automation platforms.
- Rolled out a partner program immediately with embeddable functionality so other product teams could use our tech, giving us exposure to their users.

These took days to build, and each one opened a new growth channel. 🚀 

The question is: what can you build today that creates a new path to customers?

🚀 Black Friday Giveaway: Free Scheduling Accounts! Today and tomorrow only, I’m giving away 100 FREE premium Meet.bot accounts, no strings attached.

Unlock unlimited access to:
 ✨ Custom-branded scheduling pages
 ✨ Our full scheduling API and MCP for your automations
 ✨ All premium features

If you’ve been curious about Meet.bot, this is the perfect chance to jump in.

How to claim:
Just sign up on our website and start using Meet.bot. That’s it. Early next week I’ll upgrade the first 100 new signups to the full premium plan for free.

No need to comment, but if you want to help us get this in front of more people, a quick “I’m in!” or anything else you'd like to say would mean the world. 🫶

Did you know you can get 12 months of Perplexity Pro for free?

This is a great way to upgrade your AI toolbox without any real risk. You can use Perplexity for deep research, summarizing complex topics and speeding up daily tasks.

The key detail: the promotion is tied to subscribing with PayPal, which is what unlocks the free period. I’ll leave the link with the details in the comments.

Thanks to Kazik Pietka for making me aware of this.

[SUNDAY REFLECTION] Something has changed in the workplace. Commitment is becoming rare. Too many people show up unfocused, unprepared, unmotivated, yet still expect a high salary. 

I don’t think most people want to be this way, but the bar to stand out is lower than ever: show up, do your job well, bring a new idea once in a while, and you’re already ahead of most.

I want more people winning, truly. But if you’re not putting in the effort… don’t be surprised if AI takes your job.

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