In 2008 Webb, then chief executive at LiveOps, a virtual call center company, was looking for a new head of product management. One of his customers recommended Bergelson. “He told me he was the best, most insightful person, in the product space we were in, in the world,” Webb says. Bergelson lights up at the compliment: “I had no idea from whence it came, but I was happy to have heard that!”

Giddily, they resume. “So I reached out and tried to recruit him, and he gave me the Heisman,” Webb says, assuming the inflection of a rebuffed lover. “But I really liked him,” he adds, channeling that asked-her-out-everyday-until-she-said-yes kind of cadence. Despite the initial rejection, the men kept in touch.

Later, and fresh off completing his book Rebooting Work: Transform How You Work in the Age of Entrepreneurship, Webb found himself preoccupied with managerial concerns. He had an idea: “There really isn’t a way to get people great coaching,” Webb says. “It’s very cool we have this entrepreneurial culture, but sometimes when you move forward you leave something behind.” That thing, according to Webb? Workplace mentorship.

Bergelson, motivated by a botched mentorship experience of his own, signed on to the effort. While at Cisco (CSCO), Bergelson had been matched by the company’s human resources department with Mike Volpi, a meteoric leader whom many insiders believed would succeed CEO John Chambers. But Volpi soon left Cisco for the venture capital firm Sequoia Capital. Bergelson was never reassigned a mentor. “All those battles I fought, those political battles that I fought and mostly lost while I was at Cisco,” Bergelson laments, “if I had had somebody to talk to I would have avoided most of those.”

Determined to prevent others from suffering a similar fate, Bergelson and Webb last year founded Everwise, a company that connects apprentices with advisors—or protégés and mentors, in the company’s parlance. Think of the service as a platonic OKCupid for the office.

It works like this: Where popular dating apps like Tinder pull Facebook (FB) data to assemble their members’ profiles, Everwise draws data from LinkedIn (LNKD) pages. In addition to offering a mobile application through which to assess its users’ interests, Everwise will also arrange a half-hour pre-screening call for each party with a concierge-like career coach. An algorithm then helps pair participants. Afterward, the liaisons—many of whom happen to be stay-at-home mothers, Bergelson notes—keep tabs, collect feedback, and nudge participants (when necessary) over a 6-month mentorship cycle.

It’s not exactly like online dating. Instead of an automated prompt urging its users to chat—e.g. “You both like things. Talk about them”—Everwise’s human intermediaries facilitate the relationship, an aspect that many clients cite as crucial to its success. This interpersonal touch helps Everwise avoid some of the pitfalls that occasionally accompany online dating: Supply and demand mismatch, a suitor’s sudden unresponsiveness, uncertainty where one stands with a recent connection. Through technology and a dollop of human intervention, Everwise aims to eliminate whatever one might term the professional equivalent of unrequited love.

Much as especially attractive people on dating apps receive the bulk of attention, so do mentors at glamorous companies who bear distinguished, exciting titles. Why lunch with Joe Dull in accounting, an up-and-coming professional mentee may ask, when you can dine with someone like Larry Page? Everwise aims to help people make meaningful connections that both parties will benefit from, rather than letting infatuation with star power run amok.

That’s not to say there aren’t hiccups. When Allison Kelly, COO at Pacific Community Ventures, a small business lending and advising nonprofit, heard about Everwise, she excitedly signed up in summer 2012. It took until fall for Everwise to find a match. “Everwise was very apologetic,” she says, noting that the company had some difficulty selecting someone who fit her stature. Eventually, she was paired with Laura Mather, a cybersecurity entrepreneur who is CEO and founder of Unitive.works, an organization that promotes diversity and equality in the workplace. “Laura was well worth the wait,” Kelly says.

Mather was equally as effusive. “To be honest, it was amazing,” she says. “From the first time we talked, I felt we really clicked.” During a particular rough patch, Mather called Kelly nearly every night for two weeks. Kelly’s supervisor had gone to Europe, and she was facing several stressful situations at work. Mather helped quell her protégé’s anxieties, taught her meditation techniques, and helped her kick an unrelenting bout of insomnia. Even after graduating the program, the two still speak regularly. Kelly has since become a mentor herself. “Heck, if online dating sites could do this well, there would be lot more happy marriages out there and a lot fewer single people,” Mather says.

Participants at other companies have also reported positive results. Mark Eisner, senior group medical director at Genentech (DNA), recently ran an Everwise pilot program with 40 employees. “It went really well,” he says. “It exceeded my expectations.” Even in the two cases where pairings did not pan out, Eisner says Everwise quickly remedied the situation. “I don’t think you would expect to see so many successful matches if it weren’t for the algorithm,” he says, adding that as a scientist, the data-driven aspect appeals to him.

Susan Lovegren, senior vice president of human resources at Plantronics (PLT), an audio equipment company, says that she has used Everwise as a way to re-inspire disengaged employees. The program provides a way for the company to show that it cares about and wants to invest in its people, she says. Lovegren conducted a 20-person pilot in 2013 and has since renewed for a second cohort of 50 people.

At the end of 2013 Everwise partnered with Virgin Unite, the charitable nonprofit arm of billionaire Richard Branson’s Virgin Group, to launch a co-developed online platform to help train and guide entrepreneurs around the world. Virgin Unite now has about 1,500 mentors on the platform and 500 entrepreneurs—an ideal 3-to-1 ratio, says Benjamin Hay, Virgin Unite’s head of strategic projects. “We want to make sure we’re successful, and doing that at scale is really quite difficult,” he says. “We wouldn’t be able to achieve success without the technology that Everwise provided.”

Sure, the story of how Everwise’s founders met is more serendipitous and organic than the algorithm-fueled matches their startup now engineers. But Bergelson remains adamant that matchmaking requires no magic. “Our vision is to help people build these personal boards of directors, but to do it in a way that scales using software,” Bergelson says. “This is what people did with the online dating industry 25 or 20 years ago. People were like, ‘That’s crazy going to go meet somebody down at the bar—you need to make sure there’s chemistry and all that.’ We now know that’s not true.”

Bergelson cites data to emphasize his point. Where there was once a stigma around digital dating, now 1-in-4 married couples in the U.S. have met online, he says. (Actually, a 2013 study commissioned by the dating site eHarmony found that relationships between more than a third of couples that married between 2005-2013 began online. On the other hand, a Pew Research Center study from the same year found that only 1-in-20 married or committed couples in the U.S. say they met online, though eight times as many American singles report having used online dating sites or apps. Those figures, of course, have probably risen since.) But Everwise’s own success rate speaks for itself. The overwhelming majority of people who mentor through Everwise—upwards of 94%—say, at the end of the mentorship cycle, that they would like to reapply for another protégé, according to Bergelson.

Chemistry? Alchemy? It turns out that neither are necessary to make a match. Just an algorithm for a professional life lived happily Everwise after.

Update, May 11, 2015: This article has been updated to include the results of a 2013 online dating study that appeared in the scientific journal Proceedings of the National Academy of Sciences.