As Chief Operating Officer, Steve Drew oversees day-to-day operations and drives the company’s growth, performance, and technology enablement. He partners across investment, development, finance, marketing, and people teams to ensure McWhinney operates as one integrated platform. Steve brings more than 25 years of experience in digital transformation, fintech, and real estate technology. He has led major initiatives in product management, system architecture, CRM and investor portal integration, and capital formation technology, all with a focus on creating seamless experiences for investors and stakeholders.
Before joining McWhinney, Steve held executive roles across fintech, real estate investment, and digital marketplaces. As SVP of Marketing, Strategy and Technology at Caliber Cos. he led marketing modernization and technology initiatives that supported capital raising. Previously he spent nearly a decade at CrowdStreet as a founding team member in multiple executive roles, where he helped build the largest commercial real estate investment platform and supported more than $4 billion in capital raised and a successful Series D round. He also held leadership roles at Sage Software and Radiant Systems, where he advanced product, business intelligence, and financial technology efforts.
Looking ahead, Steve is focused on scaling McWhinney’s digital and operational infrastructure so the company can offer an industry leading investment experience that is accessible, transparent, and efficient. This work supports McWhinney’s commitment to innovation, financial discipline, and creating places people love.
Affiliations:
Member, Board of Directors, Candlelighters for Children with Cancer