DevOps requires cultural transformation which is the most challenging aspect of overall transformation as changing mindset and behavior is more demanding than implementing tools and strategies. The challenge turn out to be even more complex when it is applied in a Fintech providing services in a highly regulated industry. The complexity expands when Fintech is large-sized and have been carrying 20 years old legacy processes and systems. The speaker has led the transformation in such an organization as Head of DevOps for more than 3 years and want to share his challenges and the experience of how he overcame them. Some of the challenges are still outstanding for which struggle is going on, which will be shared in the session with their road map.