Hey guys, it's your host Blaine here. And today we've got some great news. We're launching a brand new private community for uploading and it's all about building your personal brand the right way. The community will feature access to some of the world's best content creators, some of who you've heard on uploading, and more to come. The best news, this community is absolutely free to join, but there will be a vetting process to make sure that you're serious about your content and personal brand and you're ready to support others. So if you want to scale your content, boost focus, stay consistent, grow your personal brand and connect with other top creators, make sure to apply@castmagic IO Uploading community. We'll drop the link in the show notes and hope to see you there. Welcome to today's episode or workshop of uploading.

Today we're joined by Chris Cunningham, a founding member and head of social marketing at ClickUp, the AI powered productivity platform, which is valued at, I believe like $4 billion, maybe, maybe even more than that today. But Chris has been instrumental in shaping ClickUp's brand voice since 2017, transforming their social presence into one of the most influential B2B SaaS with over a billion impressions in 2024 alone, regularly generating 200 million plus impressions per month. So in today's workshop, we're going to cover how ClickUp's content started small and evolved into a viral content machine. Uh, we'll talk about key pivots and breakthroughs and moments that define ClickUp's content strategy and the lessons that Chris and the team have learned along the way. Um, we'll talk about building repeatable content systems and as well as a team culture to be able to keep things moving, keeping things engaging week after week. Um, and also ways to measure and monetize your content engine. Like, how does it work once you're creating content? How does it actually translate into, into business? Everything from a big bet like a Super bowl bowl ad, to more regular, everyday sort of content series. And lastly, we'll be just talking about advice in general for creators, marketing teams looking to scale up their content and turn it into business.

So with that, Chris, I'll let you kick us off. Why don't you give us a little bit about your background and maybe how you got involved with ClickUp from the early days.

Yeah, so I'm on. The original four started ClickUp. It's been a wild ride. Before that, it was the same crew we had. We, we started an agency, we did really well, in the early days in Charlotte, North Carolina, made some money, decided we wanted to take on something bigger. So from there, we built a social media app that was a competitor to Snapchat called Memory, because at the time, Snapchat would erase all your memories in seven seconds. So we thought we had this great play. We were doing really well.

We moved to California. We were living in a house together in Palo Alto, building this, and everything was going great. I thought we were gonna be the next Zuckerberg until Snapchat came out. With Snapchat Memories, we lost all our money, lost everything. But in the interim, we had built a tool because we didn't really like Asana, Trello, Jira. We thought it was weird that he had to log into so many different types. Like, developers would use Jira, you know, marketers would use Asana. Just didn't make sense to us.

So we had built our own internally and we decided to go to market with that. It's kind of our last hoorah until we had to go back to, like, work, you know, different jobs. There's our last, like, entrepreneur run, and we locked ourselves in a house, you know, then Palo Alto. Kept working, worked crazy hours, and we, you know, first. First year was tough. I was our first sales rep. First, like, customer service rep and really marketer. And so I was just kind of trying to be scrappy.

I remember closing our first deal and then starting to close more deals. But ClickUp's grown a lot since then. I think we've really kind of shown that customization is really important in software. And then now branding as well. So I've shifted my focus. Who knows? Our first sales rep. I'm obsessed with marketing. I love content and I love creating leads that way.

And so I think now I can build more leads for ClickUp by creating content rather than just, you know, closing deals on the phones. So, yeah, my role now is head of social marketing. I get pretty big goals every few quarters. The first one was 100 million impressions in a month. I hit it, then I hit 200 million, and now they've asked me to find a way to hit 300 million. So I do that by creating what I would call different shows. I have many different pages because obviously it's hard to get one page to hit that many. I focus on different platforms.

I talk to experts from all different types of platforms. I'm trying to be omnipresent, be a little bit everywhere. But, yeah, that's. That's my mission now.