Celestine Maddy: "Nobody wants the chick that's doing the creative to be in charge, you know?"

Kimberly interviewed Celestine Maddy in March 2025. Celestine Maddy is an executive marketer, who has held leadership positions at Pinterest, Reddit, Foursquare, the Wing, and Emerson Collective. She is the founder of Wilder Quarterly, a publication for a growing world, and co-author of Wilder Life. Celestine and Zocalo’s founder Kimberly Aguilera have a beautifully long history and we are delighted to have her as our first interviewee.

🗨 Hi Celestine! Do you want to start by telling us who you are and what you do?

My name is Celestine Maddy. What do I do? That's a great question. Actually, I was a tech executive, and maybe I'll be a tech executive again, but I think with the changes in tech, I guess I'm a strategic marketing and comms consultant. So weird. It's a weird thing to say. It's not a good title.

🗨 What energizes and inspires you at work—and outside work?

I like difficult problems. I like scaling. I like finding product market fit. I like the startup stages of ambiguity when you're building something. And that's always given me a lot of energy. That’s why working at Pinterest wasn’t fulfilling, because it was already done; everything was kind of set in stone. Every job I had we were in the hunt for something. Whether it was the Wing [a women’s-only co-working space], which was trying to figure out its business model, or Foursquare [a digital platform], which was changing from consumer to B2B; that in-between space is very energizing. I find it personally energizing to think about what comes next. We can't be in capitalism forever. What comes next? We can't raise our kids like this forever. I find ideas at the edge of how we're going to operate as a culture really interesting right now, because it's obviously not working.

🗨 What pivotal experiences in your life or career have been influential in shaping your leadership style and values?

I think the Wing collapsing [after various public controversies, including allowing racism to go unchecked] was super influential. Trying to align your personal values with corporate needs, I found that to be challenging and gratifying. Stepping down was like voting with my values even though I was pretty sure no one was ever going to ask me to be CEO again. That was weird: CMOs don't become CEOs. It just doesn't happen. Nobody wants the chick that's doing the creative to be in charge, you know? I definitely disliked it, or had a hard time saying no to that gig, even though I felt like I had to, because it was for Black Lives Matter. It really brought my ethics together with my leadership style. That was a big moment.

Being at Reddit and realizing that team matters most. Like that job taught me that if you don't take care of your team, you're sunk. Team first, no matter what. And I've stuck to that ever since, and it always paid dividends. That's really shaped my leadership style, for sure.

And really, just trying to be as truthful as possible at work has definitely been one of my things. Like calling a spade a spade is hugely invaluable in corporate structures, if you ask me because we're all kind of like playing a little bit, or pretending a little bit. So anytime that you can just speak truth to power, I find it to be good leadership.

🗨 How will talent and culture strategies need to evolve in the coming years?

You know what's really funny about this? I was just talking to someone about how we worked at Undercurrent [a consulting firm in the 2010s] and those ideas are still new, and that was like 10 or 15 years ago. Still people haven't heard about them: consent versus consensus; like all of the same corporate pitfalls still really exist. I don't know when corporate organizational design is going to take a leap forward. I really wish it would. I thought remote was going to do something, but it doesn't seem like anything sticks, because we're in this capitalist environment. So I don't know. That's a great question.

I wish we would make some advancements in how we work together, but I just don't see that coming. Like Zuckerberg and everybody rolling back whatever DEI efforts we had made. Or not even DEI, I would just say care is being walked back. We really were working on empathy for a while there, but I don't see that anymore.

🗨 In your experience, what are the ingredients of a successful hiring process?

I'm the worst hirer. That's really the thing I've learned. I really let everybody else do the hiring. I think a good process is really when you have a standard set of questions that you're going to ask everybody. I think those are always really good. I think cross-functional people interviewing is really good as well. Some of those best practices really do work well. I don't see the point in reinventing the wheel. A good recruiter makes a big difference. Surfing LinkedIn is very different to having a recruiter that has a network. That's huge. I always see a difference when that happens.

🗨 What advice would you give to individuals aspiring to work in tech?

I think tech is still best when you're inventing your own way. Like going to work for Meta for the next 20 years, I don't think that's going to be satisfying for anybody. I think the things that are happening on the edge are more interesting. So startups in climate science and all those things. I think those are good places to hang out. Social media and all that stuff is dead. I would not go work at Facebook. I would not join Instagram or something like that, or Discord, or Blue Sky. I would look for real tech. I think that's where the interesting stuff is going to happen.

🗨  What brings you joy?

I want to meditate. I think meditating is the best thing that I can do. It's totally changed my life. It brings a lot of clear space and a lot of gratitude and healthy processing of what is a crazy life, right? This is a crazy life. Work is a crazy idea. How we work, working all the time, being plugged in, the rat race, capitalism, the news cycle. Like, I just think meditation is really the thing that's changed me most over the last year.

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