Amy earned a Bachelor of Science degree from Brandeis University, graduating magna cum laude. She began her career investing personally in small-scale redevelopment projects, reinvesting gains to build scale and attract institutional partnerships.

Beyond her professional work, Amy is active in philanthropy and civic engagement, particularly in the arts and youth development. She serves as Artistic Director of Windy City Playhouse, an award-winning nonprofit theater company in Chicago known for immersive productions. She is a member of the Young Presidents’ Organization (YPO) and the Economic Club of Chicago, and has been recognized by the Jewish United Fund’s “36 Under 36” and the Illinois Real Estate Journal’s “Woman of the Year – Broker.”

Chief Executive Officer, Clear Investment Group

Amy M. Rubenstein is the Founder and Chief Executive Officer of Clear Investment Group (“CIG”). With more than two decades of experience in commercial real estate, she has established a track record for identifying and repositioning distressed multifamily assets that others overlook. Since founding CIG in 2003, Amy has led transactions totaling nearly half a billion dollars and overseen the revitalization of more than 150 workforce housing communities across the United States. Her disciplined approach—grounded in operational execution, conservative underwriting, and market insight—has consistently generated durable, risk-adjusted performance across market cycles.

Under Amy’s leadership, CIG has evolved into a vertically integrated, institutional-quality real estate investment platform with a national focus on distressed and value-add workforce housing. The firm’s mission is to deliver asymmetric returns to investors through opportunistic acquisitions, rigorous asset management, and community revitalization—creating both financial and social value without compromising performance.

CIG’s inaugural institutional vehicle, Clear Opportunities Fund I, closed in 2024 with over $83 million in commitments from family offices, pension funds, and other institutional investors. Building on that success, Clear Opportunities Fund II is targeting $250 million to $300 million in equity to scale the firm’s strategy nationally. The fund has already completed its first close of approximately $30 million, including capital from a new endowment investor, marking a significant step in the firm’s expansion and institutional momentum.

Amy’s insights on market dislocation, distressed real estate, and ethical investment have been featured across leading financial media. She appeared on Bloomberg Businessweek Daily to discuss the evolving opportunity set in multifamily and was profiled in Legacy Through Impact, which highlighted her focus on aligning investor outcomes with community impact and sustainable growth.