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Jaan Jagomägi has worked in a variety of roles since 2003. Jaan began as CEO of FFT Technologies OÜ in 2003 and then moved to Oskando Ltd. as CEO in 2005. In 2007, they became Business Area Manager at REGIO Ltd. and Co-Founder of AVL Express OÜ. Jaan also was Product Manager at Reach-U that same year, with responsibilities including product ownership, leading software development teams, improving software development processes, and providing support to sales teams. In 2012, they became Account and Project Manager at Titanium Systems OÜ. In 2014, they were Founder of Japri OÜ, providing software product development and product management consulting. Jaan was also Co-founder of Triptec OÜ that same year. From 2015 to 2018, they were Cofounder of RateChain, linking local car rental suppliers with global customers. Finally, they were Product Manager / CTO at UpSteam from 2018 to present.

Jaan Jagomägi obtained their MBA in Entrepreneurship and Technology Management from the University of Tartu in 2012. Prior to that, they earned a Bachelor's degree in Economics - Investment and Markenting from the University of Tartu in 2004. Jaan is also a Certified Scrum Product Owner.