When Raina Moskowitz W05 stepped into the CEO role at The Knot Worldwide last year, she brought with her a track record of building businesses around customer needs. Previously the chief operating and marketing officer at Etsy, Moskowitz has also spent much of her career focused on how technology can bring people together. Now, she leads a platform that connects soon-to-be-married couples with the vendors who make their big day possible — from florists to DJs to hair and makeup artists.
“I’ve done a lot of listening to our team and customers,” she says. “About two million couples get married in the U.S. each year, and the vast majority interact with our platform in some way. We also have more than 200,000 wedding professionals on the platform in the U.S., most of them small-business owners. If we do an incredible job meeting their needs, everything flows from there.”
Wharton Magazine caught up with Moskowitz as this year’s wedding season gets underway to talk about her first year as CEO, how the company is leveraging AI to enhance the planning process, and why she believes human touch will propel the season’s biggest trend.
Wharton Magazine: Looking at your time as CEO so far, what stands out as a defining accomplishment?
Raina Moskowitz: Two things really come to mind. The first was articulating our company vision. When I entered last year in January, I heard a deep pride in the company but a desire for clarity about where we were heading. Clarity is extremely important. It drives everything we do, from organizational design to decision-making. The second piece is building the team to deliver on that vision. I’ve focused on complementing the remarkable tenure and talent we already have with new skill sets and perspectives. As CEO, those two areas are foundational.
WM: What are some of the most meaningful product innovations you’ve introduced?
RM: Our focus across the board is removing friction — making it easier for couples to plan and for vendors to run their businesses. On average, couples are hiring 13 vendors and making hundreds of decisions, so there’s high stakes and high emotion. The magic happens when we successfully connect couples with vendors who are going to bring their day to life.
It’s also important to be where our couples are. Recognizing that 36 percent of couples now use AI to start the wedding-planning process, earlier this year we launched a new app within ChatGPT. Couples who start on ChatGPT are now able to be connected with trusted vendors on The Knot right on the platform. It’s the same thing on social media — we’re investing to make sure that our vendors show up wherever couples are spending time.
On the vendor side, we launched a brand-new WeddingPro app to make managing their businesses easier. Time is very valuable for our vendors, so we’re focused on helping them get discovered quickly and communicate faster with couples. That includes AI-powered tools that help streamline responses.
WM: What industry trend do you think will have the biggest impact in the coming year?
RM: Interestingly, it’s not technology — it’s authenticity. Couples are surrounded by inspiration, especially on social media. But what we’re seeing in our data is that they don’t want a cookie-cutter wedding. They want something that reflects their relationship, tastes, and personal style. They want to turn inspiration into something that feels uniquely them.
WM: The Knot publishes a lot of industry research. How does that influence the broader ecosystem?
RM: Weddings are a $100 billion industry in the U.S. alone, so there’s a lot of interest in understanding what’s happening. One of the things I love is that weddings are resilient. People continue to prioritize them even amid economic volatility.
Importantly, vendors rely on our data to help them navigate. Many small businesses don’t have access to a lot of data, so our insights help them plan and stay on top of what couples are looking for.
WM: What energizes you most about your role?
RM: Traveling to different markets and understanding what’s top of mind for couples, vendors, and our team. I always bring a notebook and am constantly taking notes to feed those insights back into the organization. That feedback loop is incredibly energizing.
WM: What’s the hardest part of the job that people might not see?
RM: Saying no to good ideas. There’s so much opportunity to innovate in this industry, and the team brings forward outstanding ideas. But we can’t do everything at once. That’s why having a clear strategy is so important — it gives you the framework to prioritize and make the right trade-offs. Still, it’s never easy to say no to something that could be great.
WM: What lessons from Wharton still influence you today?
RM: Teamwork is a big one. I still remember being in those huddle rooms in Huntsman Hall, figuring out who is going to do what. That is still my day-to-day and what is so amazing about how Wharton is structured. It’s about getting the best out of your colleagues and working together to solve real problems. That’s another piece from Wharton that gave me a great head start — introducing me to relevant scenarios that have carried through my career.
WM: How have your previous roles shaped your leadership approach?
RM: After Wharton, at American Express, I had the opportunity to work across multiple functions and learn from exceptional role models and leaders. That shaped a lot of my trajectory and understanding of leadership. At Etsy, my time was defined by learning how to surround myself with the best possible team. When I think of all the things I’ve done in my career, it comes back to building teams. That’s the key to success and why I spend so much time thinking about talent and hiring wonderful people to chart the next chapter of our growth.
WM: What drew you personally to the wedding industry?
RM: There’s a fascinating intersection here. On one hand, there’s rapid advancement in technology. On the other hand, people are craving connection. Weddings are one of the few times where all the people you love are in a room together. To play even a small role in that moment is incredibly meaningful. And again, we’ve got hundreds of thousands of vendors who are getting discovered through our platform. Bringing those two sides together is what makes this work so special.
