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From Support to Success: Creating Opportunities That Last

Serena Alaily – CEO – Aspire Chicago

Serena Alaily, CEO of Aspire, joins the Work Inspired Podcast to discuss leading with both heart and data, and why disability inclusion is central to strong communities. She shares how Aspire creates dignified homes, prepares individuals for meaningful work through immersive training, and continues to expand across Chicago, Lake, and Cook County. The conversation also explores future workforce opportunities, the role of AI in training, and what it means to build pathways for people to live full, independent lives.

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Featured Guest

Serena Alaily

CEO 

Serena Alaily is the CEO of Aspire, where she is leading a bold movement to build an inclusive future for everyone. Guided by a deep belief that anything is possible, she is advancing Aspire’s mission to connect people with disabilities to ever-greater possibilities in learning, jobs, and safe places to call home.

Under her direction, Aspire is expanding partnerships, reimagining community homes through universal design, and laying the groundwork to double its impact by 2032. Serena has championed major milestones, including securing a $9.2M federal grant to launch Aspire’s Employment Training Program, a first-of-its-kind workforce model that opens new career pathways for young adults with disabilities while helping companies address turnover and talent shortages.

Her leadership is shaped by strategic expertise and her lived experience as a parent of a child with a disability. That lens fuels her commitment to building communities where everyone belongs and can thrive. Today, she leads Aspire with a blend of heart and discipline—grounded in lived experience, powered by possibility, and driven by the belief that we build a better world when we build it together.

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Podcast Host

Kimberly Sulivan

Kimberly Sullivan

Executive Vice President

BOS Holdings

Kimberly brings over two decades of experience leading workplace strategy and delivering client-focused solutions across a wide range of industries. As Executive Vice President at BOS, she draws on her deep knowledge of contract furniture and commercial interiors to guide complex projects from vision to completion. Kimberly has a strong track record of building lasting client relationships, mentoring sales teams, and driving organizational growth through thoughtful leadership and strategic planning. She is passionate about creating environments that not only support business goals but also elevate the experience of those who use them every day. Now, as the new host of Work Inspired, Kimberly is excited to lead the conversation on the future of work, spotlighting the ideas, people, and spaces shaping the way we work today and tomorrow

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Podcast Guest Host

Jerry DiCola Headshot

Jerry DiCola

Founder, Certified Instructor, Consultant

Inspiring Consultant Service logos

Jerry DiCola is the founder of Inspiring Consultant Services, LLC and a subject matter expert in IFMA training program development. With more than 20 years of experience leading global projects and building high-performing FM teams, he also delivers IFMA and BOMI certification courses. Jerry previously served as President of the IFMA Chicago Chapter (2013–2015) and remains dedicated to mentoring the next generation of facility management professionals.

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Want to be on the show? Know someone who would be a great guest? We’d love to hear from you!

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