Shane Kovalsky, Founder and CEO, Mystery

Shane Kovalsky is the Founder and CEO of Mystery, a startup that provides employee events and rewards. Mystery organizes events and provides software tools for companies to coordinate logistics and track attendee engagement. From the company’s founding, Shane’s vision was to leverage technology to build deeper connections through shared experiences. While Mystery navigated a true pivot , the company’s north star of optimizing for happiness remains the same.

 But about that pivot. Mystery launched in 2019 as a way for couples to plan a surprise “mystery” date night. Couples would sign up for a date night package, receive a hand-delivered gift box, and the date’s itinerary was slowly revealed as the evening unfolded. The company planned thousands of Mystery date nights and was beginning to launch in new regions, when the pandemic brought things to a halt in March of 2020. As Shane puts it, “We went from having a great business to an illegal one in about seven days”.

 While the world transitioned to remote working, Mystery leveraged its logistics and planning tools for a new use case: employee engagement and team building. The company began providing virtual events such as mixology classes, casino nights, musical comedy, chocolate making – the list goes on. At a time when many people felt more isolated than ever, Mystery provides connection.

 Today, Mystery helps customers bring their company’s culture to life through shared team experiences. The company serves over 1,000 customers, from tech giants Amazon, Uber, and Stripe to a Girl Scout troop and a woman-owned karate dojo. Customers use Mystery’s software tools to select event options from qualified vendors, and measure employee engagement, reactions, and connection to team members.

 Prior to founding Mystery, Shane led sales and product development at Convoy, a trucking and logistics software company. Shane began his career as a co-founder of Seattle Web Pros, a website development shop that served small businesses, and went on to oversee product design at Porch.com. Throughout his time in these roles, Shane saw the power of well-designed products that felt good to use, combined with behind-the-scenes logistics software that made planning effortless. Armed with this insight, he set out to build the platform to amplify joy through peer-to-peer connection.

 We are thrilled that Shane recently announced the successful close of the company’s $18.5 million Series A round, led by Greylock and with participation from Frontier Venture Capital, Coop Ventures, Endeavor, and Moving Capital.