Steve Drew

Chief Digital Strategy Officer

As Chief Digital Strategy Officer at McWhinney, Steve Drew leads the development and launch of the company’s digital equity-raising platform, overseeing strategy, implementation, and cross-functional collaboration to align with McWhinney’s long-term vision. With over 25 years of experience in digital transformation, fintech, and real estate technology, Steve brings a deep understanding of product management, system architecture, and business strategy. His expertise in digital equity raising, CRM implementation, investor portals, and AI-driven analytics ensures that McWhinney remains at the forefront of innovation, creating seamless and efficient digital solutions for investors and stakeholders.

Before joining McWhinney, Steve held executive leadership roles at companies specializing in fintech, real estate investment, and digital marketplaces. Most recently, as SVP of Marketing, Strategy & Technology at Caliber Cos., he led the company’s marketing transformation and technology initiatives, optimizing CRM integrations and capital formation strategies. Prior to that, he spent nearly a decade at CrowdStreet, where he was a founding team member and served in multiple executive roles, including VP of Product, Marketplace Transformation, and Business Operations. At CrowdStreet, he played a pivotal role in building the largest commercial real estate investment platform, overseeing digital equity raising strategies that facilitated over $4 billion in capital raised and secured Series D funding. His experience also includes leadership roles at Sage Software and Radiant Systems, where he drove product development, business intelligence, and financial technology innovations.

Looking ahead, Steve is focused on elevating McWhinney’s digital strategy by creating an industry-leading investment platform that enhances accessibility, transparency, and efficiency in real estate equity raising. By integrating cutting-edge technology, data-driven decision-making, and a seamless user experience, he aims to position McWhinney as a digital leader in real estate investment. His vision aligns with McWhinney’s commitment to innovation and financial discipline, ensuring the company continues to deliver exceptional value to investors.

Affiliations:

• Member of the Board of Directors Candlelighters for Children with Cancer