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Gajaba (Gary) Hewamadduma started their work experience in 2009 as an Assistant Controller at ReachLocal. Gajaba (Gary) then worked as an Executive Director - Accounting at MySpace from 2010 to 2011. From 2011 to 2012, they served as the Vice President of Finance at BetterWorks. In 2013, they became the Chief Executive Officer at CFO Plans Inc., where they focused on transitioning finance back-offices into valuable and real-time information centers. In 2017, Hewamadduma joined Cleanshelf as an investor and also took on the role of Managing Partner at Talentshell. Gajaba (Gary) continued their investor roles at Bamboo, ZEROS, and RASA Indian Grill in the subsequent years. Finally, in 2020, they became a Managing Partner at Invoisync.

Gajaba (Gary) Hewamadduma has a strong education history, starting with their completion of a Bachelor of Science degree in Computer Engineering from the University of Moratuwa. Gajaba (Gary) attended this institution from 1993 to 1997. Following this, Gajaba pursued further education by enrolling in The Chartered Institute of Management Accountants, where they earned the degree of Chartered Management Accountant. This program focused on Financial and Management Accounting and was undertaken from 1992 to 1995.

Continuing their educational journey, Gajaba attended Pepperdine Graziadio Business School from 2002 to 2004 and completed their Master of Business Administration (MBA) degree with a specialization in Finance. This program provided him with a strong foundation in the field of Business and Finance. Lastly, Gajaba participated in the CPA Australia Program to further enhance their educational qualifications. However, specific details such as the duration and field of study are not provided for this program.