Jessica Cherry: Leader in Workplace Transformation
Jessica founded ReImagining the Workplace to share her ideas for cultivating thriving workplaces, to engage and collaborate with others with the same mission, and to amplify the voices of those who are successfully forging the path to positive change.
Always a keen observer of workplace dynamics, Jessica draws from her personal experiences, education, and nonlinear career path when contemplating the future of work. She traces her views on leadership to her many years competing in equestrian sports. And her background in television and law have shaped her perspective on the roles of well-being, career development, and purpose in igniting top performance.
Passionate about transforming workplaces to inject more humanity, and intensely curious about diverse viewpoints, Jessica rejects the idea that workplaces must be soulless places that overvalue conformity, competition, and adherence to the status quo. Instead, she envisions a modern workplace that ignites performance and supports well-being by embracing differing perspectives, redefining leadership, rewarding collaboration, and creating safe spaces where individuals feel empowered to show up and engage authentically.
What People are Saying…
On Innovation
"For many years now, Jessica has been sharing fresh ideas on innovating the way we train and engage talent in the legal industry and the vital role that workplace culture plays in learning and development. She’s been a thought leader contributing to the important conversation on how law firms and legal departments can create inclusive, healthy cultures and has used her platform to amplify the voices of many leaders in this space with diverse backgrounds and perspectives. It’s a very necessary conversation that I look forward to her continuing to drive."
Joe Green, Chief Innovation Officer, Gunderson Dettmer
On Bringing Humanity to Law
"Jessica was my first mentor. We worked together when I was a first year associate, and at that time, she was often referred to by the partners in the group as the “union rep” because she was always looking out for associates’ quality of life, mental health, and work/life balance. Jessica brought a kind and human touch to the world of large law. She truly cared about developing associates and helping them become the best lawyers they could possibly be, while encouraging them to carve out time to be other things too. As a partner now, when mentoring associates, I often think, 'what would Jessica do?'. Jessica was a rarity in large law, focused on attorney well-being and professional development, rather than the billable hour."
Gina Lauriero, Partner, Morgan, Lewis & Bockius LLP
On Mentorship
"Like most in law school, I was unsure where I would end up. I was interested in employee benefits, but did not know anyone who practiced in the area. I came across an interview of Jessica discussing her experience working as an employee benefits and executive compensation attorney. I took a leap of faith and reached out to her on LinkedIn for some career advice. Before even contacting me back, she had already surveyed her colleagues about my questions and was prepared to connect me to additional attorneys in the field. I was blown away by her generosity and willingness to share her experience and network for my benefit. Throughout the years, Jessica has empowered me to achieve my goals: whether it was handing me off to her next connection, providing me with a personal recommendation, sending me educational articles on all matters of employee benefits, or spending time on the phone talking me through my path to success. I ended up practicing employee benefits law, and I owe it all to Jessica and her absolute belief in me and willingness to share her world with me. Even today, Jessica continues to be a mentor that I depend on."
Bradley Horne, Associate, Smith & Downey