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Cy Scott

Co-founder & CEO

Headset Inc.

An entrepreneur at heart, I have experience starting companies, working for startups and doing time at large organizations.

Currently, I am the Co-founder and CEO of Headset Inc., an analytics company for the cannabis industry designed to help operators make informed decisions based on data. We have a focus on operational and market intelligence, helping our customers make sense of this rapidly emerging and changing industry.

Before Headset, I began my career accelerating the adoption of legal cannabis as the cofounder of Leafly. Since it’s inception, I’ve worked with our talented team to grow Leafly into a platform that serves 6M visits monthly with multimillion-dollar revenues. Leafly had a successful exit, sold to Privateer Holding a leading company in the cannabis space with backing from institutional investors, such as Peter Thiel’s Founders Fund.

Prior to Leafly, I worked on’s redesign first as an engineer, then as part of the product team and was responsible for getting Kelley Blue Book’s first ever patent. I also worked as Sr. Product at Source Interlink (now TEN: The Enthusiast Network), a large publishing company with properties like Motor Trend and Automobile, working on their transition from traditional print to a digital-strategy.