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Hassan Osman
Head of Enterprise Transformation @Grand Circle Corporation
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WORK HISTORY
Head of Enterprise Transformation @Grand Circle Corporation
Boston, MA, US
Leading the adoption, engagement, and sustained success for large-scale, cross-functional initiatives as the Head of Enterprise Transformation at Grand Circle Corporation.Reporting to the CEO, this role focuses on change management and organizational readiness around key transformations, including AI integration, customer-facing technology launches, cultural evolution, and agile ways of working. Key responsibilities include:Strategic Leadership • Define and lead enterprise change strategies aligned with business priorities and cultural values. • Partner with the Executive Team and senior leaders to set vision, milestones, and success metrics. • Build and lead a high-impact change management function to scale across all divisions. Communication & Engagement • Craft compelling communication and storytelling that connect employees to the “why” behind change. • Launch internal campaigns and engagement programs that build excitement, trust, and adoption. Training & Enablement • Design and implement tailored learning programs to equip teams for new ways of working. • Collaborate with People & Culture to embed change capability into leadership and development programs. Measurement & Continuous Improvement • Establish KPIs, feedback loops, and dashboards to track adoption, sentiment, and ROI. • Report insights and recommendations to executive stakeholders to inform decision-making. Cross-Functional Partnership • Act as the bridge between strategy and execution, ensuring alignment across business units. • Facilitate workshops and listening sessions to gather input, reduce resistance, and foster ownership.
EDUCATION
Harvard University
ALM
American University of Beirut
Bachelor's
MIT Sloan Executive Education
Executive Certificate
Carnegie Mellon University
M.Sc.
SKILLS
ABOUT HASSAN OSMAN
As the Head of Enterprise Transformation at Grand Circle Corporation, I currently lead the adoption, engagement, and sustained success of large-scale, cross-functional initiatives.Reporting to the CEO, the role focuses on change management and organizational readiness around key transformations, including AI integration, customer-facing technology launches, cultural evolution, and agile ways of working. Prior experience:• SVP of Professional Services at NWN (a $1B AI-powered technology solutions provider). I ran a $100 million services business, leading 200+ project managers and engineers.• Director at Cisco Systems, leading the centralized Program Management Office (PMO) for the Americas Technology and Transformation Group portfolio projects and 150+ project and program managers).• Manager at Ernst & Young (EY), providing consulting services for Fortune 500 companies such as General Motors, Dell, and Bank of America.• Research assistant at Harvard University studying challenges related to virtual teams.• Wrote 9 Amazon bestselling books readers) and published 17 bestselling courses on Udemy students).I run two free newsletters to help busy executives with simple frameworks that save time and multiply team effectiveness.• Leadership 80/20 (5-min email every Sat): AI for Leaders (5-min email every Thu): Views are my own and not those of my employer
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