Lindsay Gaskins (she/her)

Chief Executive Officer

Lindsay Gaskins leads with a commitment to expanding access to housing, health, and opportunity for LGBTQIA+ individuals and others facing systemic barriers.

A pioneering executive, serial entrepreneur, and board leader, Gaskins brings more than 20 years of experience scaling innovative ventures and strengthening mission-driven organizations. She is known for building durable systems, aligning teams around clear strategy, and leading organizations through growth and transformation with discipline and purpose. A people-first leader, she prioritizes trust, transparency, and shared ownership—creating cultures where individuals feel valued, accountable, and empowered to perform at their highest level.

Before becoming CEO, Gaskins served as Board Chair of Chicago House, where she partnered closely with staff, trustees, and leadership to guide strategic planning, advance racial equity priorities, and strengthen governance during a period of expansion. Her transition reflects both continuity and a clear commitment to growing the organization’s impact at a time when the need for systemic change is urgent.

Gaskins is Co-Founder of BREAKTHRU, where she built the Spectrum of Leadership Empowerment®, an identity-based platform advancing career and economic mobility for underrepresented leaders. She previously served as President of New Business Ventures at CCA Global Partners, leading digital transformation and launching technology platforms to support independent businesses nationwide. Earlier, as Co-Founder and CEO of Marbles: The Brain Store, she scaled the company into a nationally recognized brand, building the systems and culture required for sustained growth.

Across nonprofit and private boards, Gaskins is known for her clarity, decisiveness, and collaborative leadership, helping organizations navigate complexity with a focus on equity, accountability, and measurable outcomes.

A proud member of the LGBTQIA+ community, Gaskins lives with her wife and their three children in Oak Park. For her, leading Chicago House is deeply personal. She believes housing is a human right—and that real progress requires not only meeting immediate needs, but reshaping the systems that have left too many people without access to stability, dignity, and care.