Sandeep Singh, MBA
Director, Project & Program Management @ CAA Club Group
About
Information Technology leader with a committed focus on empowering people, strengthening organizations, and guiding technology toward outcomes that serve the broader good. I approach digital transformation with responsibility, humility, and a people-centred philosophy across insurtech, fintech, traveltech, member services, and customer experience domains. In recent years, I’ve broadened my expertise to include the strategic use and governance of artificial intelligence. My focus is on understanding how AI can elevate human capability, strengthen decision-making, and support safe, ethical, and environmentally responsible innovation within the enterprise. I build high-trust, high-performance teams that deliver customer-centred solutions and create sustainable value across the organization. I believe technology reaches its greatest impact when it elevates individuals, supports communities, and contributes to responsible global progress. Recognized for shaping long-range strategy, fostering cross-functional collaboration, and leading with analytical precision and compassionate judgment. My engineering mindset guides my decisions with clarity, purpose, and integrity, particularly as emerging technologies reshape the future of work and society.
Canada
Greater Toronto Area
Information Technology & Services
Property and Casualty Insurance, Technology Change Management, Engineering Change Management, Change Project Management, Artificial Neural Networks, Artificial Intelligence (AI), Product Development, Product Management, Product Marketing, Product Design, Risk Assessment, Project Delivery, Program Management, Agile Methodologies, Digital Transformation, Agile Project Management, Project Management, Strategy, Risk Management, Budget Management
Experience
Director, Project & Program Management
CAA Club Group
Thornhill, Ontario, Canada
• Lead the enterprise-wide IT Program & Project Management practice in a matrixed, shared-service environment, governing strategy, frameworks, delivery standards, and execution discipline across all CAA Club Group lines of business, including insurance, travel, and roadside operations. • Direct a portfolio of complex, multi-year technology initiatives advising executives and senior leaders on prioritization, risk exposure, delivery readiness, and long-range transformation planning. • Steward the full IT financial portfolio, optimizing capital and operating expenditures, ensuring fiscal discipline, and aligning spend with enterprise vision, mission, goals, and strategies. • Provide strategic oversight and delivery leadership for all IT projects, spanning digital platforms, core systems, data, cybersecurity, and infrastructure, while ensuring alignment with organizational priorities and member experience outcomes. • Lead and develop a high-performing team of project and program managers, fostering a culture of trust, clarity, and consistent execution while maturing enterprise delivery capability. • Guide application design and solution architecture reviews, shaping technology approaches, operating models, and implementation pathways to ensure feasible, sustainable, and scalable outcomes. • Oversee vendor and partner governance, including contracts, SOWs, performance management, and RFP processes, ensuring accountability and strategic alignment with delivery objectives.
Program Manager
Workplace Safety and Insurance Board (WSIB)
Toronto, Ontario, Canada
Program Director
International Financial Data Services (IFDS)
Toronto, Ontario, Canada
Program Manager
CAA Club Group
Thornhill, Ontario, Canada
Manager Projects
Cognizant
Toronto, Ontario, Canada
Program Lead
Manulife
Kitchener, Ontario, Canada
Sr. Consultant
Software Catalysts LLC
Boston, Massachusetts, USA
Worked as a consultant for their Boston area clients: • Fresenius Medical Care • Wellington Management Company • John Hancock Financial • Cognition Financial • Brigham & Women's Hospital
Electrical Engineer
Labsphere, Inc.
North Sutton, New Hampshire, USA
Education
Cornell University
Dual Executive MBA, Samuel Curtis Johnson Graduate School of Management
Queen's University
Dual Executive MBA, Stephen J.R. Smith School of Business
Boston University
Computer Science
Specialization: Cryptography & Information Security
Michigan Technological University
Electrical Engineering
Specialization: Digital Signal Processing
Sandeep Singh, MBA's Contact Information
Phone
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