How this startup went from facilitating dates to employee engagement – GeekWire

How this startup went from facilitating dates to employee engagement – GeekWire

How this startup went from facilitating dates to employee engagement – GeekWire

A mystery performer playing for a Mystery virtual event. (Mystery Image)

Mystery, the Seattle startup that launched two years ago with mystery dates, is riding the success of a pandemic-induced pivot that has turned the focus toward morale-boosting virtual events for distributed and hybrid teams and companies.

Mystery is even calling its B2B brand of employee engagement “morale as a service.”

The change in direction isn’t the first for the startup, which first launched by helping facilitate a surprise night on the town for couples, complete with dinner, drinks, entertainment and transportation that was all kept a mystery. In March 2020, as the COVID-19 pandemic hit and quarantine orders kept people inside, Mystery tried a new service called “Night In,” to cater to people stuck at home while also helping businesses hurt by the outbreak in Seattle.

Now it’s attracting some of the biggest companies in the world, including Amazon, Microsoft, Starbucks, Apple, Zillow and more by using its event-planning expertise to surprise and delight workers.

“We’ve taken everything we learned from Night Out and Night In and turned them into a tech-centric platform,” Mystery co-founder and CEO Shane Kovalsky said. “Our technology allows us to create the best virtual events in the world by codifying magical experience design — but we won’t say much more than that because it’s the mystery behind Mystery.”

Is there magic, left, in the Mystery? (Mystery Photo)

Mystery offers six virtual experience categories, including artistic events, classes, games, relaxing events, tastings, and performances.

“Not all teams are the same — sales teams are different than engineering teams, and we’ve used our data to build unique experiences that fit each team,” Kovalsky said. “Each of those categories have dozens of experience options.”

Not all of the events are secret, but the company strongly encourages them to be for a number of reasons. Mystery believes that the best experiences are those that push people and whomever they’re with just outside of their comfort zone — and people usually don’t pick those experiences. Expectations are also out the window when a team has no idea what’s in store, attendance improves, and the bonding experience is better.

The pivot is working, according to the company. Mystery says its business is already 10 times bigger than it ever was and the total market is massive. The company has built a network of hundreds of vendors. And it’s growing as a company, too.

Mystery, which has raised $4 million to date, now has 26 employees. It’s doubled in size since the start of the pandemic, with most team members fully remote and distributed across seven states. Among recent notable hires:

Recent hires at Mystery, from left: Ahmed Owainati, Jackie Wagner and Mae Mirkin. (Photos via Mystery)
  • Ahmed Owainati, VP of engineering, was one of the first employees at Convoy and he spent six years at the Seattle trucking marketplace. (Kovalsky also previously worked at Convoy.) Owainati also spent almost five years at Amazon.
  • Jackie Wagner, chief of staff and head of sales, is a lawyer and MBA who most recently ran the sales team at
  • Mae Mirkin, head of design, was previously a principal designer at Amazon who helped launch new services for delivery operations such as Amazon Flex and lockers.

The B2B model and virtual experiences will be Mystery’s focus for the foreseeable future. Kovalsky did say that the original Night Out in-person product is not off the table.

“However, when you turn onto an open lane highway with no one on it, you don’t take a back road, you hit the gas,” he said. “Right now we’re only doing virtual events for businesses, but that’s just the tipping point. We’ve already successfully done thousands and thousands of in-person events in the past, so we’re set up for success to do those again.

“But we’ll keep what that looks like a mystery for now,” Kovalsky added.

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