Building the 100x Org - The CFO as AI Architect with Dan Zhang, CFO & CBO at ClickUp

**Ray Rike** (0:08)
Welcome to today's episode of the AI to ROI podcast. Today I'm joined by Dan Zhang, the Chief Business Officer and Chief Financial Officer at ClickUp. Dan and I will be exploring and covering five topics today. The catalyst for the expanded AI charter at ClickUp.
Why the CFO is uniquely positioned to lead AI transformation.
How to identify which AI initiatives are actually working. Fourth, what it takes to move hundreds of knowledge worker roles at once, not just individuals adopting a AI tool. And lastly, how Dan is turning 100X into a real blueprint and framework with measurable financial outcomes. So with that, Dan, we're going to cover a lot in 30 minutes. Hope we can do it. Could you take a moment and give a brief overview of your background, for our listening audience?

**Dan Zhang** (0:57)
Thank you for having me on the podcast Ray.
So I zigzagged my way into the CFO role. My prior life was a stack of jobs that just didn't add up in a traditional career lens. I started out as a journalist and I also did some entry-level selling, which was a very humbling experience. And then I came to the States for business school and then I got into finance. And right when the path looked straight, that I took a detour to take on the very first generation of the RevOps role. So back before the title even really existed, this was more than 10 years ago. And then I came back to the finance track. So I would say my history, because since we're on this AI topic, has really evolved since I took on the CFO seats. In 2024, I was mostly tinkering individual productivity hacks. And last year, in 2025, it moved to, how do I move my team, right? The team level productivity. And then this year, that is the organizational wide AI transformation. How do I see the results coming up in my financial statement, P&L statement?
So I think that's a totally different animal that I'm happy to share some of the real lessons and voice from operators on this show today.

**Ray Rike** (2:15)
Look forward to that. I did not know about the RevApps background. I don't know if you know, but I created a company called RevOp Squared back in 2008
Then when I first founded Benchmarkit, we actually called ourselves RevOp Squared, but we were doing mostly benchmarking, so I evolved it to Benchmarkit. But I love that zigzag role, because I think it's the best way to become a true well-rounded business executive. And you fit that role, because you're not only a CFO, you're a Chief Business Officer, and you're leading the AI transformation at ClickUp using something that you call the 100x org. So can you tell me, what was the catalyst for structuring the AI mandate this way?

**Dan Zhang** (2:55)
I would say we came to this mandate kind of north of the Last Standing Heart way.
Then we tried both extremes, and both failed.
So first is we ran like the top down mandate, right? The CEO and all the C-suites, we just make it non-negotiable. AI is absolutely number one priority. Every all hands was AI, AI, AI. Everyone just go. And then we swan to the bottoms up, right? The thousands of flowers blooming, hackathons everywhere, tokens burning, big showrooms of people, demoing the cool stuff, and it felt great. And last year, we did it for a whole year. And then me and the CEO, we sat down, and we looked at what we actually got, like what is actually being put into the production. And it was not pretty. And it's token wasted, it's people burned out. And we have an issue that's called the agent's sprawl, right? Just like, you know, you have a thing called work sprawl, you have fragmented tools and contacts. Now you have agents running around in your workspace in your email, providing, you know, slops and burying the real human inputs.
And I think what's more important is we realize that there is an anxious and insecure workforce that couldn't tell if the AI thing is a tool or a threat. So that's when it clicked for us that you cannot drive it from only the bottom or purely kind of let it experiment. And because the CEO mandate just dies in the middle, right? It really needs someone to kind of move the middle in order for AI to move the needle. And so that's what we discussed. Like, hey, like how about put the CFO in charge because we naturally already see everything in the business, the inputs and outputs, and we're the person in charge of translating all the strategy into the execution. So that's where we came to this conclusion is just to expand the CFO scope to be the driving the end to end AI transformation for the entire company.