Behind the Scenes of OkCupid — A Spirited Team Collaborates to Improve the Dating Experience

The Short Version: At any given moment, about 150,000 singles are on OkCupid, a free dating app and website, hoping to make a connection. On a typical day, OkCupid users send an average of 7.3 million messages and go on over 40,000 first dates. From the site’s famed match algorithm to their passionate team, OkCupid has a lot of strengths driving their success in the dating industry. Since the site launched in 2004, their uniquely analytic approach to dating has yielded phenomenal results and changed the lives of millions of online daters. Today, a diverse group of 52 team members continue to innovate, expand, and improve the site to create real relationships between people of all orientations, backgrounds, and belief systems.

Most people know OkCupid by the impressive numbers, the longstanding reputation, the cute name — but not much thought is given to the people behind it all. Maintaining such a massive and effective dating site, for free, is no easy undertaking.

At OkCupid, hard-working, fun-loving, snack-eating individuals come together to positively influence the dating world. We decided to delve a little further into the team responsible for creating tens of billions of mutual likes and matches. Yeah, billions — they’re a pretty big deal.

Jane Reynolds, OkCupid’s Senior Editor, graduated with a degree in English at Dartmouth College.

Jane Reynolds, Senior Editor at OkCupid, has been with the company since October 2016, and she took us through what it’s like working for one of the world’s largest dating websites. “We’re definitely community-focused,” she said. “We’re interacting with people in various states of dating and relationships, and on various levels and platforms, every day.”

OkCupid has recently expanded their marketing team, seeking to become more engaged with their audience on social media and other channels.

That effort is most readily apparent on the OkCupid blog, where you’ll find a wealth of information, humor, and anecdotes aimed at young singles. From a tongue-in-cheek farewell poem to 2016 to an in-depth breakdown of deal-breakers for OkCupid users, the blog amuses and advises daters so they know they’re not alone out there in cyberspace.

“We want to reach out to our user base through social media,” Jane said, “and also put OkCupid in the physical world through merchandising and events.”

In Manhattan’s Chelsea neighborhood, OkCupid’s office occupies a floor of an old 12-story brick building. The open floor plan facilitates cross-communication and transparency. Working face to face at their desks, engineers, web designers, marketers, and data scientists collaborate at every level of the company. “No one’s title fully encompasses all that they do,” Jane said.

Every morning, OkCupid provides employees with a catered breakfast to start the day off right.

CEO Elie Seidman leads by example and sits alongside all team members in the open space.

The office has a modern look and feel with long rows of desks, three conference rooms, versatile focus pods, and a lunch area where you can always find a beer in the fridge or a snack in the cabinets.

“I’ve worked at several different firms in the tech industry, and there’s no question that this has been the best experience I’ve had,” an OkCupid software engineer wrote on Glassdoor.

During designated Hack Weeks, the team puts all meetings on hold and collaborates on features they want to see on the site. Team members in all departments enthusiastically bounce ideas off one another to improve and expand OkCupid’s reach in the dating world. For them, it’s all about helping people connect in meaningful ways.

“Everyone is super invested in every aspect of the site,” Jane told us. “We’re really interested in helping each other make the best product we can.”

OkCupid doesn’t throw singles at one another in random matches — they’re much more refined than that. The site’s mathematical approach pioneers more interesting and authentic dating between people of all ages and backgrounds. The team calculates attraction by tracking user behavior and applies over a decade’s worth of knowledge to maintain an inclusive, intuitive, and ingenious dating environment for singles.

It’s a daunting, data-driven mission — but it’s also incredibly fun and fulfilling.

Crunching the numbers on their blog, the team openly discusses research questions like what flirtation looks like on their site — what people are talking about and how it changes over time — so daters can learn from user trends. OkCupid team members put themselves in the shoes of modern online daters and rely on hard data to offer solutions for daters on the site.

Watch on

In their quest to improve, the team overhauled their Quickmatch feature to help users learn more about another person before they swipe left or right. Quickmatch shows you a condensed version of the user’s profile, complete with bio, compatibility rating, and notable personality traits proven to be important to daters. This feature means users’ interest levels are based more on personality than looks.

“We don’t want it to be a surface-level experience,” Jane said with feeling. “Through Quickmatch, you have the means to see more matches while getting to see more of their individuality upfront, too. Things like more photos, their profile, and their personality.”

Users that “like” each other will be notified by an encouraging message in their inboxes. According to the blog, “It just makes sense: authentic connections are made over the things you care about, not how you look in a selfie. So give Quickmatch a try.”

From making the questions more topical to introducing features that make the site more interactive, the OkCupid team is never done tweaking the site to give users easier access to authentic connections.

The OkCupid team is full of personality, from goofy vegans to snarky wordsmiths, and their diverse strengths make the website a more helpful place. They tackle projects with humor and creativity, constantly brainstorming new ways to connect people faster, easier, and smarter. Of course, with roots as a techy startup, OkCupid’s company culture has plenty of perks that keep their talented staff happy to come to work every day.

Team members get into the spirit of the holidays by participating in a company-wide party.

First off, the company feeds the creative energy of team members by, well, feeding them. Catered breakfasts fill the office with the smell of coffee and baked goods every morning.

On Tuesdays and Thursdays, OkCupid also offers employees free lunches from local restaurants. Chefs come into their kitchen to whip up treats like handmade ice cream or freshly made crepes for everyone. Yum! These delicious meals bring the team closer together and lighten up the workday.

From company costume contests to crowded conferences, the OkCupid team brings a sense of fun to their work. It’s a dynamic office environment, with monthly happy hours encouraging employees to relax, maybe play a round of ping pong, and laugh over a few beers.

The holiday season brings even more joy to the offices. The company’s traditional Secret Santa event gives employees a chance to (discreetly) learn more about each other and come up with a personalized gift. As the presents are handed out, team members bond and show their appreciation for their coworkers.

“Everyone is really thoughtful, and we have a fun mentality,” Jane said. “As a team, we get our work done, but we know how to have a good time, too.”

OkCupid is a world-class dating site (and app) made with care and imagination. This online space deliberately emphasizes personality, accessibility, and fun as it welcomes hundred of thousands of daily users in search of conversation and connection.

Behind the success, the streamlined features, and the exacting match algorithm, we found a group of dedicated, witty individuals putting in the hours day-to-day to support online daters around the world. OkCupid employs over 50 people who are passionate about helping singles form lasting bonds online and in person.

OkCupid’s team of math enthusiasts takes an analytic approach to the process of attraction.

Theirs is a mission of love. Some team members have dated — and even met their spouses — through OkCupid, so they understand the intimate impact a dating site can have on individuals. Their work has the potential to change lives, and that’s something the fun-loving team takes very seriously.

“Love and dating are an important part of people’s lives, so it’s easy to feel strongly about what we do,” Jane said. “We see the results, and hearing those stories about couples who met on OkCupid is a really great motivator for our team.”