Leadership Team

Andrew Paradise is the CEO and founder of Skillz. Prior to Skillz, Andrew founded AisleBuyer, which was best known for pioneering mobile self-checkout prior to its sale to Intuit (NASDAQ: INTU) in 2012. Andrew has been the founding inventor behind companies in different technology sectors ranging from eCommerce to image recognition to HR technology. Andrew was named to the San Francisco Times’ 40 under 40 class of 2018.

Casey Chafkin is the Chief Revenue Officer and co-founder of Skillz. Prior to Skillz, Casey was the VP of Business Development for AisleBuyer (now Intuit GoPayment). Casey received his B.S. in economics from Duke University and his MBA from Harvard Business School.

Jason Roswig joined Skillz in August 2022 and serves as President, responsible for all of the Company's operations functions. Prior to joining Skillz, Roswig served as a Managing Director in Blackstone's Private Equity and Portfolio Operations groups where he had oversight of the financial and operating performance of Blackstone's technology portfolio, since 2019. Prior to Blackstone, Roswig served as an Expert Associate Partner in McKinsey & Company's Corporate Finance and Organization practices from 2012-2018. Prior to McKinsey & Company, Roswig served in a variety of Corporate Development roles at General Electric from 2000-2012.

Roswig holds an MBA from Columbia Business School and a Bachelor of Arts degree in Economics and German from Bowdoin College.

Andy Dahlinghaus is the General Counsel at Skillz, where he oversees legal, compliance, and regulatory matters.

In his past roles, Andy has led best-in-class Legal and Compliance groups in Fortune 500, FTSE 250 and private equity-backed companies, including JuuL Labs, ConvaTec, Covidien, and Medtronic. Prior to going in-house, Dahlinghaus was an attorney at international law firm Arent Fox, where he represented a wide variety of clients in high-stakes litigation and government investigations. Prior to joining Skillz, he managed legal, compliance, and data privacy functions at Clario, a leading healthcare research and technology company.

Andy received his B.A. from Indiana University Bloomington before graduating from The George Washington University Law School.