Chicago House is undergoing a leadership transition as CEO Michael Herman retires and Board Chair Lindsay Gaskins, a leadership development executive who has served on the organization’s board for several years, steps into the role.
The leadership change, announced April 6, is part of a planned succession at one of Chicago’s largest LGBTQ+ housing providers that has been designed to ensure a smooth transition, according to officials. Gaskins said she informed the board she planned to apply for the role and recused herself from the search process.
“It’s bittersweet,” said Herman, who has led the organization since July 2019 and informed the board years in advance of his planned retirement. “I got a little emotional at the end of my last day because this hasn’t just been a job for me—it really has been my passion work.”
Chicago Houseprovides housing, health care and supportive services for LGBTQ+ individuals and people living with HIV, with a focus on those experiencing homelessness or housing instability.
Herman said he stepped into the role of CEO during a period of uncertainty, followed by the COVID-19 pandemic, and helped bring stability to the organization while leading it through a period of significant growth.
Herman previously worked at Chicago House beginning in 2006, serving as chief development officer before leaving for several years to focus on capital fundraising. He returned to the organization in 2019 as CEO.
His work as CEO included expanding the organization’s housing footprint across Chicago, including new developments on the South and West sides, such as the Englewood Family Homes that opened in 2024 and a planned housing site in East Garfield Park.
The organization also developed new service models, including programs focused on supporting people living with HIV as they age.
Herman also worked to reestablish housing as the organization’s central focus, positioning Chicago House as a primary housing provider with wraparound services.
“Chicago House did a lot of things well, but you need to be known for the number one thing you do well—and that’s housing,” Herman said. “We were doing a lot of other things, so it started to look like housing was one of the things we did. I think my legacy is that I restored the idea that Chicago House is primarily a housing provider.”
Gaskins said she plans to build on that foundation while bringing her own leadership approach to the role. She added that her top priority is maintaining Chicago House’s mission while continuing to evolve how it serves clients.
“Mission beats everything,” Gaskins said. “We serve an amazing set of folks in our community. We need to keep that stable in this environment, and we need to continue to innovate and think about how we can serve our clients in different ways.”
Gaskins comes to the role with a background in leadership development and cross-sector work. She most recently led Breakthru, a leadership development organization focused on supporting underrepresented leaders, and previously worked in cooperative business models and startups.
She said her background will inform how she approaches growth and new programs at Chicago House.
“This is a good time for creativity to come to the table,” Gaskins said.
Gaskins, who identifies as a member of the LGBTQ+ community, said the work is also deeply personal.
“This is my community,” Gaskins said. “And I want Chicago House to continue helping people in my community thrive, find dignity and hope as they make it through some of the hardest times that many people face in their lives.”
She said she is particularly focused on ensuring the organization can continue to meet growing needs among people experiencing housing instability, while building on new service models introduced in recent years.
Gaskins said the transition comes at a time when demand for housing and supportive services continues to grow, particularly as economic inequality and housing instability impact LGBTQ+ communities.
“We’re not going to sit still,” Gaskins said. “We’re going to keep finding ways to meet the needs of our community.”