Dapo Olajide
Director, Development @Infrastructure Ontario
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WORK HISTORY
Director, Development @Infrastructure Ontario
Toronto, ON, CA
Leading the structuring, negotiation, and execution of complex real estate partnerships - including land sales, ground leases, and joint ventures - integrating transit-oriented development with major infrastructure investments - on public lands.• Designing and implementing innovative commercial and financial structures that optimize development value, unlock long-term public land potential, and balance risk through performance regimes and aligned incentives.• Overseeing financial modelling, market analysis, and strategic evaluations to test deal structures, assess capitalization strategies, and guide investment decisions for large-scale developments.• Managing cross-functional transaction teams and external advisors (legal, financial, technical) to advance planning approvals, draft and close binding agreements, and secure post-closing obligations.• Implementing competitive market processes to attract top-tier developer partners, presenting investment opportunities and deal recommendations to senior leadership and government stakeholders.• Collaborating with municipalities and public agencies to secure affordable housing and other community benefits, assess impacts to deal pricing, and identify funding solutions that preserve deal value.
EDUCATION
The University of British Columbia
Master of Science (M.Sc.), Planning
International School, University of Lagos (ISL)
High School, Social Sciences
University of Waterloo
Bachelor's Degree, Development Economics and International Development
SKILLS
ABOUT DAPO OLAJIDE
Dapo is a seasoned real estate development professional with a decade of experience in structuring and executing complex development transactions, acquisitions, and public-private partnerships. With a strong background in transaction advisory services, he has successfully led and managed large-scale capital projects across the real estate and infrastructure sectors. His expertise spans financial modelling, development strategy, and commercial structuring for speculative land, mixed-use developments, non-market housing, and district energy investments.As a Development Director at Infrastructure Ontario, Dapo plays a key role in formulating and negotiating real estate partnerships that unlock development value on surplus public lands. He has successfully structured high-profile land transactions that advance transit-oriented communities, affordable housing, and large-scale redevelopment projects across the Province. His leadership in public-private partnerships has enabled the delivery of innovative financing and delivery models that balance public policy objectives with market-driven development strategies.Previously, as an Investments Associate at Northcrest Developments, he contributed strategically to the business plan and investment strategy for the phased redevelopment of the Downsview Airport Lands. Earlier in his career, he served as a transaction advisor at KPMG and Steer, where he shaped the commercial strategies of major public development projects across Canada and globally.Dapo holds a Master of Science in Planning from the University of British Columbia and a Bachelor of Environmental Studies in International Development from the University of Waterloo
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