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Chemutai Diana has worked in a variety of roles since 2018. Chemutai began their career as an IT & Finance Intern at Nyayo Tea Zones Development Corporation before becoming a Customer Service Representative at Ndege Chai Sacco. In 2019, they worked as a Census Aide at the Kenya National Bureau of Statistics and as a Corporate Sales and Marketing Executive at Safaricom PLC. That same year, they also took on the role of Business Development and Operations Associate at RUH Solar, where they were responsible for Documenting the Sales Agent Journey Plan, enforcing the Approved Sales Agent Journey plans, and managing the server hierarchy. In 2022, Chemutai Diana took on two roles: School Business Support Lead at Jackfruit Finance and Business Operations Associate at Azuri Technologies, where they were responsible for logistics analysis, inventory management, and customer technical support supervision.

Chemutai Diana has a Bachelor of Business Information Technology from Jomo Kenyatta University of Agriculture and Technology, where they studied IT with Accounting and Finance. Chemutai also attended Loreto High School.