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Jamie McDonald has a diverse work experience spanning various companies and roles. Starting in 1998, they worked as a Product Manager at Microsoft until 1999. They then moved to Expedia, where they served as the VP of Destination Services from 1999 to 2005, playing a significant role in customer acquisition and leading the in-destination business. In 2006, Jamie founded Sparkroom, a SaaS software company focused on the buy side of lead generation, where they served as the Founder and CEO until 2011. During this time, they built a leading platform in the education lead generation space. From 2011 to 2020, Jamie co-founded and co-led Hubdoc, an automated document collaboration platform for accountants and small businesses. They automated document management and conversion into usable data for cloud accounting platforms. In 2019, Jamie joined Xero as the Executive GM, Product, Accounting, and Global Services, a role they held until 2020. Currently, Jamie serves as the CEO of A2X, a company automating e-commerce accounting.

Jamie McDonald's education history begins with their enrollment at Upper Canada College from 1980 to 1989. However, it is worth noting that no specific degree or field of study was provided for this period. Afterward, Jamie attended Duke University from 1989 to 1993, where they obtained a Bachelor of Arts (BA) degree in Economics. Later, from 1996 to 1998, Jamie pursued their Master of Business Administration (MBA) at Northwestern University's Kellogg School of Management, specializing in Finance and Entrepreneurship.