We used to take connection at work for granted. We hung out in the office and got to know our teammates in the cracks between the work. The trust and norms critical to working with others were constructed organically by shared experiences small and large, lubricated by spilled coffee and inside jokes. Work was more human, and the humans made it more fun.

Work in this new world looks permanently different. The pandemic has accelerated the digital transition, freeing entire industries from the mental prison of the 5-days-in-the-office norm, and unbundling the functions of the physical office. It can’t be undone.

Better tools (SaaS HR, project management, video, chat and productivity, multi-player creation like Figma) all make previously-inconceivable online coordination possible. So we continue to tick through our tasks. But what about culture and community?

In organizations where culture is weak, you need an abundance of precise rules and heavy processes, choking out innovation and a sense of ownership. In organizations where community is sparse and relationships are weak, workers both take less risk and leave their jobs with less regret.


Can we build connection and culture in the age of digital work? In almost a decade at Greylock, I’ve never seen such a universally hungry response from leaders to a problem statement.

As one Co-founder/CEO of a rocketship Greylock backed company said to me, “Didn’t even read the Mystery product page, and I don’t know what they do, but the answer is yes, we’ll try it. Any sort of service we could pay for to turn-key improve engagement or morale is high ROI. Given the 10X-unlocked remote job market, the war for talent is raging, and we are bottlenecked on talent. These investments which I would normally not consider urgent now become critically important to the company’s success.”

When evaluating markets as an investor, I love to see a combination of desperate need, massive available spend, and a terrible status quo. Employee engagement has all of those factors. But, somewhat counterintuitively, I also love to see skepticism that any better technology-enabled solution exists. The skepticism around virtual events is my favorite flavor, because it is both extremely strong and obviously wrong. I’ve heard leaders say:

“No event over Zoom could ever be fun. They’re all awful.”
“You can’t build trust or relationships over a video event.”
“We’ll try it, but I expect it to be terrible.”

We can reframe the questions, and the tone changes:

  • Have other important interactions moved to video?
  • Is video the richest virtual communication medium we have?
  • Can relationships be built and deepened online?
  • Can we do 10X better than current expectations for corporate virtual events?

The answer is obviously yes, it just takes ingenuity and work.


Mystery is the easy button for team morale. They offer fully-managed virtual team events with essentially infinite variety, hosted by a network of vetted experience partners, from baristas, to rappers, to Dungeons & Dragons masters, to A-list celebrities. They do so at high quality, high scale, and affordable cost with software for administration, automation, experience management and personalization, powered by an employee interest and interaction graph.

To close the loop, Mystery measures outcomes, from surveys to integration with HR/employee engagement systems. Mystery is as much an experience design and science company as it is a technology company. They are creating a structured container for shared experiences that reliably lead to outcomes, such as new deep connections, trust in leadership, sense of belonging, intra-team cohesion, and cross-team connection – key elements of being happy at work.

On the provider side of the business, Mystery is partnering with a growing community of high quality experience partners. Mystery is able to fill hosts’ schedules with recurring and predictable demand, in some cases becoming their primary source of income and dramatically growing the size of their businesses. We see hosts actively direct pre-existing customers to book through Mystery, because Mystery allows hosts to do what they really love: share personalized delightful experiences and connect with people.

When we interviewed partners, one told me, “I’ve never made so much money in 15 years of doing comedy. I’m moving into a nicer apartment, and I’m taking my girlfriend out to dinner.” We love that Mystery is enabling high quality local entertainers, artists, and entrepreneurs, and allowing them to bring their businesses online.

As with all investments at Greylock, we’re investing in Mystery because we love the team. Mystery started as an IRL consumer experiences company, quickly scaling until they hit the brick wall of the COVID pandemic. Founders Shane Kovalsky and Brennan Keough have “earned understanding” of experience design and scalable operations from this history of producing consumer events. They have the empathy for their providers that comes from spending weekends with the suppliers of a marketplace (truckers, at Shane’s previous company Convoy). They’re building an exceptional technical, operations, and GTM team. And they have the vision, resourcefulness, customer-orientation, and missionary zeal of great entrepreneurs.

Their decisive pivot to focus on virtual team events last year is paying off with rocketship growth. Mystery has seen huge demand from the market, and is serving everyone from Series A startups to Amazon, brokering hundreds of reliably great events per month. Customers are thrilled to have a partner in this critical area. Fellow Greylock investor Corinne Riley and I are excited to be leading the Series A investment for Greylock, and I am joining Aviel Ginzburg on the board.


Fundamentally, Mystery is transforming the way we think about employee engagement and team morale. They’re changing team events from a seldom-scheduled, often dreaded, high-friction and expensive purchase with vague objectives, to a strategic, one-click tool to reliably drive business-critical engagement outcomes. This is the first “lever” that leaders have to actually change engagement. We believe Mystery will become a category-defining company, helping every team pull that lever (and others to come). If we’re going to spend a lot of time on video, we can make it a more joyful and connected way to work.

You can try Mystery with a single event. They are hiring in every role!

I recently sat down with Shane on the Greymatter podcast to discuss how the virtual event platform provider is addressing employee engagement. You can listen to our conversation here.


Corinne Riley

Corinne works with early-stage founders who are creating data and AI products at the infrastructure and application layers.

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