WeddingWire is helping engaged couples and wedding vendors find the perfect match

By Christianna McCausland / Photography by Rachel Smith and courtesy of WeddingWire

Do not tangle with Martha Stewart over table etiquette.

That was the lesson Tim Chi learned in 2007. Chi had pulled together about a half-million in funding for his fledgling online wedding marketplace concept, WeddingWire, which was aimed at connecting engaged couples with wedding vendors. The site had shown some promise in its test city, Washington, DC, but it needed cash to scale. Chi’s team was in a New York boardroom with representatives of Martha Stewart Living Omnimedia and the domestic diva herself when the incident took place.

“I remember the menu exactly,” says Chi. “Quiche, salad, dessert. I remember thinking the plates were small, but hey, it’s New York. I thought maybe New Yorkers didn’t eat a lot.”

As the working lunch moved forward, Martha abruptly stopped the proceedings. “May I ask,” Chi recalls, “why you are using the dessert plates for your entrees?”

Today, he has about 10 witty responses to her question, but at the time he was flummoxed that with $5 million on the table, he’d been called out for using the wrong plate. Luckily, Martha let the faux pas slide, WeddingWire got the funding, and now he gets a good laugh out of retelling the story.



Chi, 39, is a person who laughs easily. This is a man who, along with the rest of the management team, willingly participates in a spoof video that kicks-off the annual company off-site meeting. His prior works include a lip-synced version of Carly Rae Jepsen’s 2012 pop hit Call Me Maybe, playing an air-headed model in a Zoolander take-off, and waging pingpong war to Taylor Swift’s Bad Blood.

Chi engages people with his humility, his humor and his rapid-fire intelligence. It is those qualities, as much as having had a good idea at the right time, that have helped him build WeddingWire into a $70 million business with nearly 800 employees.


WeddingWire can trace its origins to Chi’s own experience planning his wedding. When he and his wife were married in 2005, theirs was one of eight weddings they attended that year. Chi got to see a lot of wedding planning up close, and what he saw seemed broken. Couples struggled for transparency and clarity around how things were purchased, and what they were actually buying. It seemed like a huge buying decision where you really didn’t know what you were getting until the big day.

“All these people I knew who were really good at organizing their own lives were having the same difficulty going through this planning process,” he recalls.

At the time, Chi was still working at Blackboard, the company he co-founded in 1998. Blackboard created a breakout learning management system that allowed academic institutions to take teaching online. The company had grown to over 1,000 employees and gone public with a valuation topping $750 million. Chi had started to think about what might be next.


In researching the wedding industry, he realized that not only was wedding planning painful for engaged couples, it was also a challenge for wedding vendors, many of them small businesses, perhaps with only one or two employees. These vendors struggled to connect with customers. It was a disconnect Chi, whose parents owned a small architecture firm and real estate brokerage, understood. “I imagined my parents trying to find young customers, digital natives, and I realized there had to be some disconnect going on. I started to get to know the vendors and it became apparent there was a lot of inefficiency.”

“If you think of it as a buying decision, there’s really nothing else like it a couple will go through together that has all these components,” he explains. “That’s exactly why we thought there was such a need. We thought we should be able to solve some of this with technology.”

The core business concept was consumer reviews. While the act of getting on to find a review of a restaurant or using to research a vacation may be second nature now, it was in its infancy when WeddingWire began. The site created a platform where engaged couples could review their vendors and new couples could search for local photographers, say, or florists with the best ratings. On the advertising sales side, WeddingWire let anyone be listed on the site for free, though vendors pay for premium services.

Chi tapped fellow Blackboard founder Lee Wang along with Jeff Yeh and Sonny Ganguly to create WeddingWire. From a software perspective, the company borrowed from the lessons of Blackboard, where there were two distinct audiences — tech-savvy students who wanted more content online and faculty who were skeptical of the entire idea of online education. Similarly, engaged couples were demanding more online content, while many vendors were baffled by it. Distinct marketing teams address the needs of each audience.


The wedding industry is no place for cowards. As Chi explains, it’s high emotion, high spend, high risk, high certainty and highly complex. It is also very dense, with websites and magazines vying to get even a taste of the $57 billion-plus industry. Differentiation and strategic partnerships were essential to WeddingWire’s success.

Joe Holland was WeddingWire’s CFO and executive vice president of strategy from 2009 to 2014. (He’s now president and CFO of TeachersPayTeachers.) In 2007, he was working for the CFO of Martha Stewart Living and helped lead that company’s investment in WeddingWire.

“The great thing about [WeddingWire] is that it was using the internet to make a difficult transaction much easier,” says Holland. “At Martha Stewart, there’s a lot of editorial content about weddings, and the great thing about WeddingWire is they were giving you the information and the access needed to transact.

“The company was very clear, early on, on how to work within the industry,” Holland adds. Through strategic partnerships, advertisers at WeddingWire also received ad placements on sites like and

“It was a one-stop sale,” Holland explains, “even if you didn’t know that much about WeddingWire at the time. Early on, those partnerships helped build the core base of vendors and built a great brand for WeddingWire.”


In the early days, there were plenty of snafus. When WeddingWire was still in its beta stage in DC, Chi and Ganguly would attend bridal shows, but since they were neither brides nor vendors, they usually got thrown out. There was an expensive and time-consuming foray into an innovative pay-per-lead advertising offering that failed. That’s when Chi learned to listen to his customers, who simply wanted to buy directory advertising on the site — no innovation required.

“Early on, most things we tried didn’t work, but what was working was reviews,” Chi recalls. “Brides and grooms were finding value in those reviews and they, not many but some, would contact the vendors that had good reviews.”

Couples are not shy about telling WeddingWire what they want or expressing opinions through reviews, but wedding pros were hesitant. Today, everyone is on board with the reality that one’s reputation is online, whether you like it or not. Ten years ago, the idea of being open to public review scared small businesses.

“We had to tell them, ‘We know this is what consumers want,’” says Chi. “The lack of transparency was not helping the market to be more efficient. There were certainly people from the wedding pro side who did not buy into that, which is fine, but clearly now, nine years later, this is a much more accepted thing in every aspect of our lives.”

Vendors weren’t the only ones slow to embrace the concept. While there are approximately two million weddings in the U.S. each year, early funders were put off by the idea that WeddingWire would have to reacquire those two million potential customers every year.

“We saw several things about [reacquisition] that were great,” says Chi. “First, the channels to find engaged couples were narrow. We knew what magazines they were looking at, what keyword searches they were doing. The second thing, and this was probably the key, was that while we had the problem of customer reacquisition, so did the hundreds and thousands of small businesses we wanted to work with. In that respect, we were completely aligned.”


WeddingWire no longer gets kicked out of bridal shows. In fact, the company runs some 50 events nationally to build relationships with engaged couples and vendors. The technology itself is very scalable, but as Chi notes, you can’t just pop up in Chicago or New York and hope the people come.

“You have to be really discreet about what cities you launch and prep the city and make sure that when you’re available in that city, the experience is a good one for both sides of the marketplace,” he says.

To get the pulse of a city, Chi relies on data. WeddingWire has had a vice president of data science since the early days and maintains a very robust data science and data engineering department that tracks every single click and keyword search and derives insight from it. Data-informed decision making is a core value of the business.


The company has grown city by city and also through strategic acquisitions. It acquired long-time partner in June 2015, for example. In February 2015, it acquired Wedding Planner, S.L., which owns international brands like and brought a global database of 150,000 wedding professionals that accelerated WeddingWire’s international reach into countries including Spain, Brazil and France. Now WeddingWire has offices in New York, Los Angeles, Spain, Romania and Mexico. The headquarters, however, remain in DC.

“With the company’s acquisition of Bodas, it effectively layered on 14 new countries with an almost identical business model,” says Mike Beach, the company’s current CFO, noting that now the company has a platform to expand by adding new countries annually. “There are not a lot of marketplace vertical businesses today that have an international expansion strategy. WeddingWire does.”

Global expansion makes sense. The pain points for engaged couples are fairly universal regardless of location, and WeddingWire’s baseline offering is applicable across borders. Most important for the company bottom line is that while there are two million weddings in the U.S., there are 40 million globally. That’s a huge market of untapped and frazzled brides.

Those numbers — 40 million global weddings, two million in the U.S. — are pretty static. The wedding world is not. Societal shifts like the growing acceptance of gay weddings are changing the industry. Young, highly digital engaged couples are also impacting it by changing the way they want to make purchases. While Chi doesn’t foresee today’s brides going so far as to use Uber to get from the church to the reception, the instant-gratification mindset has bred a more impatient consumer.

“Particularly the millennial generation, which is squarely where engaged couples are, they expect different things around making purchasing decisions. There’s more sentiment around real-time, fast response,” says Chi.

The most important place to address that consumer sentiment is in mobile technology. “Right now, every company is looking at, or certainly should be looking at, mobile,” says Chi. Just this January, WeddingWire released its revamped mobile app.

For vendors, the company is providing more tools to help small businesses not only connect with customers but transact business through the site with offerings like online contracts and invoicing. The company is also translating its expertise into the general event space, helping customers navigate everything from planning the company holiday party to a Bar Mitzvah.


In the fast-paced digital world, Chi knows the mission can get lost, so he tries to over-communicate the purpose of the company — to make a positive impact on couples and their friends and families on an important day in their lives. As WeddingWire grows rapidly, he does this by taking new hires out to lunch once a month and candidly answering their questions. Also once a month, he brings in a speaker — everything from a chef to a news anchor to a swami — to build external perspective.

“There’s hard skills training, and then there’s being more worldly and understanding that not everything is wedding sales and mobile apps,” he says.

Chi attends all the speaker events himself. It’s part of what distinguishes his leadership style. He’s very much in his company, not over it. And he really genuinely seems to enjoy it.

“Whether it is people or environment or purpose, it’s important to go past what the daily task is. I think we do a good job of figuring out that next layer of what people look for in a workplace,” he says. “I feel very lucky that many of us, hopefully, feel we have the opportunity to work in a place that doesn’t feel like work all the time.”

Christianna McCausland is a freelance writer based in Reisterstown, MD.


Walking around the WeddingWire office in Chevy Chase, MD, there are two striking things. First, it’s fun. Like many fresh-faced tech companies, WeddingWire and its employees don’t take themselves too seriously. CEO Tim Chi believes in a top-down approach to creating a light-hearted corporate culture. (One can only imagine he had to sign off on the press release announcing that WeddingWire had purchased the Statue of Liberty and the Eiffel Tower so couples could use them as backdrops for their wedding photos. The release was dated April 1.)

In the office, there’s a small pub, a room with massage chairs, game rooms, a café that serves breakfast and snacks. The conference rooms are all themed, so when employees meet in the Bachelor Party conference room, they do so under a picture of dogs playing poker. “We don’t know what people will like, so we just try things and whatever works we’ll keep,” says Chi. “Test and iterate isn’t just on the [web]site, but within culture as well.”

“Tim is constantly looking for ways to improve the culture, whether it’s with the events we do or the office space we have,” says Mike Beach, WeddingWire’s CFO. “He’s constantly talking to people, doing surveys, running tests to see what aspects of the office space people like better. He’s constantly collaborating. The culture here is amazing and unlike anything I’ve seen at any other company.”

WeddingWire’s mission is to bring transparency to a murky planning process. Chi believes the office space is a manifestation of that mission. People can be flexible in the open workspace and claim walls and areas for expression. It’s a philosophy Chi exemplifies himself; he shares an office with Beach, Sonny Ganguly (CMO), Andrew Olek (general counsel), Lee Wang (COO) and Jeff Yeh (CTO). The shared office underscores another important belief — that many heads are better than one.

“I’m a big proponent of finding the right team at the beginning,” he says. “If you look at famous companies, there’s always two names, like [Bill] Gates and Paul Allen. It speaks to the idea that complementary people in the beginning are a good thing. I would probably never start a company entirely by myself.”

It is this humility and Chi’s high level of trust, as well as his fun-loving nature, that Joe Holland, WeddingWire’s former CFO and executive vice president of strategy, believes drives employee loyalty at WeddingWire. Holland himself only left because his family was in New York and the commute was getting too hard.

“He’s very intentional about creating a company culture where people will do great work and have fun,” says Holland. “I watched and marveled as he created this culture that was really enticing for these young, digitally savvy people in the DC area.”

That is the second thing that is strikingly apparent at WeddingWire: The staff is very young. While some people bemoan millennial employees, Chi embraces them, and the youth of the company drives corporate programming. The company provides opportunities for community service, for example, something they’ve observed is very important for that generation.

“Another vector we track very heavily is leadership development and training, because growth trajectory and career pathing is very important to the millennial generation,” says Chi. Knowing that many of his employees are coming to the company right out of college, he has four full-time sales trainers on staff. “It’s something we encourage because, quite frankly, it’s great to build talent internally.”


WeddingWire CEO Tim Chi always impresses on employees the purpose of what WeddingWire does; that they have the opportunity to build something that impacts a huge number of people each year. Here are just a few stats on the
scope of the wedding industry:

Number of weddings in the U.S. per year: 2.12 million

Average cost of an American wedding: $26,444

Average number of guests: 120

Average economic impact of one couple coming to town to attend a friend’s wedding: $540

Total wedding sales in the U.S. in 2014: $57.4 billion

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