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Jolly Matthew has a diverse work experience spanning several companies and roles. Jolly began their career as an Auditor at Phillipos & Co., Chartered Accountants from 2002 to 2005. Following this, they worked as an Accounts Officer at Aranis BPS Limited from 2005 to 2006, where they provided financial and accounting services to clients globally. Jolly then joined Vellathottam Group of Companies as a Chief Accounts Officer for a brief period in 2006, handling tasks such as finalizing accounts and managing tax returns. Jolly's next significant role was at LEGALFORCE RAPC WORLDWIDE, where they served as a Global Operations Manager from 2006 to 2021. During their time at the company, they also held the positions of Director of Global Operations and Chief Operating Officer. Most recently, Jolly served as the Chief Operating Officer at Trademarkia since 2009.

Jolly Matthew's education history includes earning a Master of Business Laws (MBL) from the National Law School of India University from 2009 to 2011. Prior to that, Jolly completed a Master of Commerce (MCom) in International Business Operations at the Indira Gandhi National Open University from 2008 to 2010.

Earlier in Jolly's academic journey, they obtained a Bachelor of Commerce (B.Com) in Commerce and Accounting from the University of Calicut between 1999 and 2001. Before pursuing their bachelor's degree, Jolly completed their pre-university education in Economics and Commerce at the University of Kerala from 1996 to 1998. Additionally, Jolly started their pre-university studies in Commerce at St. Xavier's College in 1995.