Jill Fletcher: Balancing Business, Arts, and Humanity

Jill Fletcher is an arts and environmental advocate, fundraiser, and community builder whose career connects business, creativity, and care for people. She has worked across corporate, state, and municipal government, small business, nonprofit, and university environments, including building and selling her own company.

Our conversation traced her path from graphic design to commercial printing and, later, to nonprofit fundraising. Jill described how the printing industry’s transformation from craft to technology led her to seek work with deeper human meaning. In nonprofit development, she found it — discovering parallels between sales and fundraising: storytelling, relationships, and community building. “It was a way to merge my business experience with my love for the arts,” she shared.

For Jill, kindness is about restoring humanity in systems that often prioritize efficiency over empathy. She described visiting an Amazon warehouse, where a cheerful guide contrasted sharply with the impersonal atmosphere around her. “The only smiles we saw there, aside from hers, were on the sides of the Amazon boxes,” she recalled. The moment stayed with her. To Jill, investing in kindness means valuing employees as people — not as parts of a machine. It is more than companies just adding perks. “There's no reason why people have to be miserable at work,” she said.

Her critique of “fire at will” employment policies is rooted in compassion and experience. While such laws give employers flexibility, she has seen how they strip away dignity and security. Workers dismissed for financial reasons are often treated as if they did something wrong, she noted, creating fear among those who remain. Jill believes communication and empathy are essential to balance the cold mechanics of these systems. “You have maximized efficiencies, you have maximized profit. Now you have to maximize the humanity.”

Beyond business, Jill brings curiosity and creativity into everything she does. She is part of the Yale Innovation Summit’s arts cohort, exploring a book project exploring why creative people often don't pursue art as a career. She's interested in understanding why people with artistic talents choose different career paths, and wants to investigate questions like: Why do people stop creating art? What prevents them from pursuing their creative passions? She aims to research the psychological and social factors that lead people to set aside their artistic interests.

Even the smallest act of kindness can have a lasting impact. Jill shared a personal story from the 1990s, when she was laid off during a company downturn. Soon after, a pressman she had worked with called to check in — simply to ask what happened and remind her she was valued. That small gesture still stands out decades later.

“It is not hard. It is just being thoughtful — remembering the humanity of it.”

Jill Fletcher is an arts and environmental advocate, fundraiser, and community builder who demonstrates that kindness is not separate from business; it is what makes it sustainable. Keep an eye out for more interviews.