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Oleg Fleitman, an accomplished AI and machine learning (ML) practitioner, has been awarded a 2025 Global Recognition Award for his pioneering work at the intersection of technology and ethics. With over a decade of experience in finance, healthcare, manufacturing and tech startups, Fleitman consistently championed innovations that are both cutting-edge and deeply responsible.
He holds an MBA from the University of Toronto — where he was awarded the Peter Godsoe/Scotiabank Scholarship in Financial Engineering — and is currently pursuing a Master of Science in Computer Science at the University of Colorado, with a focus on advancing his expertise in responsible AI.
Engineering AI solutions for real-world impact
At Diversio, a Toronto-based workplace analytics company, Fleitman designed a custom AI-powered recommendation system that fueled the company’s expansion and helped secure significant rounds of venture capital funding. That same system supported Diversio’s acquisition of a consulting firm to enhance its service offerings, further extending its reach across sectors including technology, finance and healthcare.
“I’m passionate about blending technology and data to responsibly manage risk and improve how organizations function,” Fleitman shares.
His work has had broad global application — supporting organizations that serve governments and international institutions — showcasing his unique ability to translate complex technical solutions into real-world, measurable outcomes.
Recognized for excellence and ethical leadership
In addition to the 2025 Global Recognition Award, Fleitman has been elevated to Senior Member status within the IEEE — an honor held by only 10 percent of members — and has served as a judge for several prestigious competitions, including the Globee Cybersecurity Awards, the inaugural Globee Artificial Intelligence Awards, the Business Intelligence Artificial Intelligence Excellence Awards, and the Annual American Business Awards — The Stevies.
His accolades reflect more than technical achievement — they recognize a holistic approach that combines strategy, ethics and real-world application. With expertise spanning finance, HR, regulatory compliance and analytics, Fleitman is uniquely positioned to shape the future of AI.
Professional excellence
At Citi, Fleitman played a pivotal role in helping the firm meet critical Consent Order milestones set by the Office of the Comptroller of the Currency (OCC) and the Federal Reserve Board (FRB). His efforts significantly strengthened the bank’s risk management and control frameworks, reinforcing its commitment to regulatory excellence.
“Establishing robust risk management and controls is just the beginning,” Fleitman notes. “It’s the diligent execution and ongoing monitoring of these controls that drive successful outcomes.”
His current work includes calibrating pay-for-performance models that align executive incentives with strong governance and risk oversight — a forward-looking approach that aims to embed accountability at the top.
Shaping the future of responsible AI
Fleitman’s contributions to AI in organizational behavior stand out. He is interested in expanding his footprint in researching ways to utilize AI techniques to detect early signals of financial instability, helping regulators address issues before they grow into larger crises.
“I strive to solve complex, high-impact problems, especially where responsible AI intersects with finance,” he highlights.
His influence continues to grow across industries, with a commitment to collaborative research and advancing the responsible use of AI at scale. Whether in financial services, healthcare or beyond, Fleitman’s work demonstrates how innovation and integrity can go hand-in-hand.
Fleitman’s planned research on early financial instability signals could transform systemic risk management nationally. By focusing on responsible AI practices, he aims to ensure that these technologies align with broader societal values. With leaders like Oleg Fleitman, the intersection of AI and finance shows great promise.
“I anticipate the future will bring more AI applications in financial services, driven by proactive risk management and enhanced compliance needs,” states Fleitman.
As technology evolves, AI’s role in detecting early warning signs of financial instability will grow. Fleitman’s work will help shape this future, directing AI to manage risk and foster responsible advancement across industries.
