At the age of 22, Sivarajah started his entrepreneurial journey with friends in the IT industry by distributing computers in Madurai. His company introduced innovative technologies such as MNC PCs, fax machines, X.400-based email, the internet, mobile phones, and open-source software to Madurai by collaborating with various principal companies.

Sivarajah co-founded Winways, an open-source software company that developed a mid-market ERP solution now serving major Tamil Nadu temples, including Madurai Meenakshi, Sri Rangam, Palani, and Masaniyamman, after pivoting from an online printing service.

At the age of 40, Sivarajah began introspecting on the challenges faced by first-generation entrepreneurs in non-metro regions like Madurai. This reflection, coupled with mentorship from K.S. Bharath, led him to discover his passion for societal impact. He founded Nativelead Foundation in Madurai to address these challenges.

Currently, Sivarajah serves as the Mission Director and CEO of StartupTN, driving entrepreneurship across Tamil Nadu. He also dedicates himself to Nativelead Foundation and contributes as a Director at Winways, fostering ecosystems that empower non-metro entrepreneurs.