Olek Shestakov is a seasoned entrepreneur, investor, and technologist with more than 25 years of experience. He has led teams and built companies across MedTech, insurtech, fintech, telecom, and media. He is a Co-Founder and Executive Advisor at Wilbur, the insurtech company formerly known as Livegenic. Wilbur delivers marketplace connectivity for claims servicing, connecting IA firms, TPAs, and carriers to the tools they need. Its open platform spans virtual inspections, contractor networks, and more. Olek Shestakov spoke at a past InsurTech NY event in 2019, “Magic Formula for Proof of Concepts,” alongside Dawn LeBlanc, Zander Steele, Victor Dan, Megan Protas, Daren Moreira, and Brian Gilman.
Olek founded and led Livegenic, a claims technology platform. It was used across four continents by more than 20 carriers. That work established him as a voice in claims innovation. The business later became part of Wilbur.
Today, Olek leads several ventures. He is Co-Founder and CEO of OxyDial, a company building medical and consumer health devices. He is also Executive Chairman of GlenFlow, a venture studio and innovation agency. He serves in the same role at ScaleGlide, an AI platform for engineering productivity. He has mentored more than 50 emerging companies.
Olek has a deep technical and academic background. He earned degrees in Computer Science and Applied Mathematics from the Moscow Institute of Physics and Technology. He also pursued a JD/MBA in international law and a PhD in international business and economics.
