Steve Obenski

ICAP Mentor
Steve Obenski is an entrepreneur, business leader, and former lawyer with over 20 years’ experience in technology, software and information services businesses.
B2B SaaS, Legaltech, Fintech, AI / Machine Learning
Company and Commercial Strategy, New Products, Go to Market


Steve has a passion for mentoring and advising early-stage to growth-stage businesses. He has deep experience in helping build scalable commercial strategies, launching new product lines, rebranding, and managing pivots, reorganizations and spinouts.

Steve was a leader at Kira Systems, a machine learning contract analysis platform widely deployed by the world’s top legal, financial, and consulting firms. There he led the commercial strategies that took the company from zero to tens of millions in recurring revenue and helped orchestrate the company’s exit to a PE-backed legal software conglomerate. Prior to Kira Systems, Steve was a general manager at Thomson Reuters, where he restructured and revitalized the business law solution product line.

Steve is involved in various AI and ML startups and scaleups, acting as an advisor and mentor. He also founded OSC Strategy Consulting, which focuses on growth stage companies launching new product lines or making other strategic shifts.

As a lawyer, Steve counseled telecommunications, financial services, and software companies on regulatory, IP and general business issues. Companies Steve co-founded include a mobile photosharing app, a nonprofit orchestra, and, an online platform for equity crowdfunding investments in rare violins.

Steve has long been fascinated by the intersection of technology and society. He has an M.A. in International Relations and Economics from Johns Hopkins School of Advanced International Studies, where he specialized in international technology business and public policy. He holds his law degree from UCLA, and a bachelor’s degree in Cultural Anthropology and English Literature from Brown University.