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Rajasekhar Maddireddy has a diverse work experience spanning multiple industries. Rajasekhar is the Founder of CoverSelf, a healthcare-focused claims accuracy platform that utilizes modern software development techniques for efficiency and cost reduction. Rajasekhar is also a Startup Mentor at Conquest, BITS Pilani and Alchemist Accelerator, where they provide guidance and support to emerging businesses. Additionally, they are an Official Member of Forbes Technology Council, contributing their expertise in the field. Prior to their current roles, Rajasekhar worked as a Senior Staff Engineer at HealthLucid, playing a pivotal role in transforming the US healthcare system through advanced analytics and behavioral finance. Rajasekhar also gained experience as a Senior Member Technical Staff at Oracle, developing web analytics software, and as a Software Developer at FatWire Software, specializing in web content management. Earlier in their career, Rajasekhar served as a Senior Associate at Headstrong.

Rajasekhar Maddireddy pursued a Dual Degree (BTech and MTech) program at the Indian Institute of Technology, Madras from 2004 to 2009. The specific field of study during this period is not mentioned.