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Jaiprakash Maheshwari has worked in various companies and held different roles throughout their career. Jaiprakash started as an Article Trainee at Khimji Kunverji & Co. in 2001, where they worked until 2004. Jaiprakash then joined Globus Stores Private Ltd as a Business Analyst from February 2004 to December 2005. In 2006, they joined HyperCITY Retail (India) Ltd. as Head of Business Planning & Analysis. Most recently, in 2018, they became the VP of Financial Planning & Analysis at Shoppers Stop.

Jaiprakash Maheshwari attended ICAI from 2000 to 2004, where they pursued a degree in Finance and completed their CA (Chartered Accountancy) qualification.