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.

Charlotte Edelman is the General Counsel and Corporate Secretary at Skillz, where she acts as chief counsel, overseeing all legal and regulatory matters affecting the company. She was also a key leader as Skillz went public in 2020.

An experienced middle-market dealmaker, Edelman has deep experience counseling companies from start-up to exit, investors, and funds. Over the course of her career, Edelman has developed broad transactional experience, advising leading companies on mergers and acquisitions, venture capital and private equity investments, and joint ventures across a range of industries, including technology, healthcare, telecommunications, retail, and consumer products.

Prior to joining Skillz in 2020, Edelman served as a member of the New York law firm Mintz Levin Cohn Ferris Glovsky and Popeo, P.C. for more than 20 years. She met Skillz’s founders, CEO Andrew Paradise and CRO Casey Chafkin, when she represented them in the sale of their prior company, AisleBuyer, to Intuit in 2012.

Edelman earned her Juris Doctor from the Boston University School of Law, and has a Bachelor’s degree from Skidmore College.

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.