Cheryl Calegari, Cole Haan’s senior vice president of marketing, is grateful for every single day.
Five years ago, Calegari told FN she was diagnosed with breast cancer and her world changed entirely. “I was working at Beats by Dre at Apple at the time when my entire world came to a screeching halt,” the executive said. “After a year of intense treatment and recovery thereafter, I can report that I bounced back cancer free, forever changed by the experience. Cancer granted me the profound gifts of being present, patient and obsessively grateful every single day.”
Looking back on her career, Calegari said that she takes “immense pride” in her decade-long journey at Converse from 2005 through 2015. “It was a period marked by transformative growth and personal development,” she said. “From the exhilarating early days of transition during the Nike acquisition era to the invaluable lessons learned alongside remarkable teams, every moment shaped me professionally and personally. Being part of a culture that valued optimism, risk-taking, and continuous learning allowed me to thrive and lead with conviction.”
“Also watching my teams grow and flourish, especially during the Olympics in Beijing 2008 and London 2010 where we forged groundbreaking paths, fills me with a deep sense of accomplishment and gratitude for the bonds formed and the impact made,” Calegari added. “I also had exceptional mentors over this decade who gave me the runway and trust to do ‘never been done before’ career defining work.”
One of Calegari’s first mentors when she was starting her career was Ilene Semiatin. “She empowered me to learn, grow and soar – the majority of what I’ve carried through the last 25-plus years of my work and personal life was shaped during my time with her,” the executive said. “Recognizing the profound impact, she and other mentors have had on my life, I’m committed to paying it forward by mentoring future leaders and embracing the lessons learned from reverse mentoring, fostering continuous growth and learning.”
For younger professionals looking to grow in the industry, Calegari noted that she encourages women to cultivate resilience, embrace their worth, and trust their intuition. “Finding the balance between grace and tenacity is vital, along with staying true to your personal convictions,” she said.
Looking ahead, Calegari is hoping to stay inspired. “In five years, I will be absolutely continuing to find inspiration in my work and the people I collaborate with and more importantly enjoying life to the fullest with loved ones,” she said.
A version of this article appeared in the June 3 print issue of FN, as part of the “Women Who Rock” special section. On June 5, FN and Two Ten Footwear Foundation honored these women at a live event in New York City.
