Boston Proper CEO Sheryl Clark's Leadership Philosophy: 'Step Back and Empower Your Team'
In this episode of Women in Retail Talks, Women in Retail Leadership Circle Co-Founder Melissa Campanelli interviews Sheryl Clark, president and CEO of Boston Proper, a specialty retailer of high-end apparel and accessories providing unique, on-trend, high-quality fashion for women over 40. Sheryl is also a Women in Retail Leadership Circle member! Listen in as Sheryl shares a few key lessons she’s learned throughout her career journey in retail (1:35), how she’s led Boston Proper to $100 million in revenue (4:25), and the critical role technology plays in the brand’s success (5:20).
In addition, Sheryl discusses Boston Proper’s concept of “Lucy” as the ideal customer profile to focus its strategy (6:10), the different customers the brand serves (7:00), and staying connected to Lucy digitally (8:10). Lastly, she shares her leadership philosophy (8:45) and what’s next for Boston Proper’s transformation, including its new brand partner marketplace, Brands We Love (10:55).
This episode was recorded last month at the 2025 National Retail Federation Big Show in New York City.
To learn more and register to attend the 2025 Women in Retail Leadership Summit, click here. Seats are nearly sold out!
Sheryl Clark is the CEO and president of Boston Proper, a distinguished women’s specialty apparel brand known for its unique and bold style. With over 35 years of experience in the fashion and retail industry, Sheryl has become a leading voice in the world of e-commerce, recognized for her ability to blend creativity with business acumen. Her leadership at Boston Proper is marked by a deep commitment to empowering women to express their individuality and confidence through fashion.
Before joining Boston Proper, Sheryl held senior roles at some of the most respected names in retail, including Bloomingdale’s, Old Navy, and The Gap. Her expertise spans product development, merchandising, marketing, e-commerce, and brand strategy, all driven by a keen understanding of the modern consumer. Sheryl’s career is characterized by her passion for innovation and unwavering belief in fashion’s power as a form of self-expression. She believes in fostering a workplace culture that values diversity, creativity and collaboration. Sheryl’s leadership style is compassionate and results-driven, inspiring her team to achieve excellence while staying true to the brand’s core values.
Sheryl holds a Bachelor’s degree in Business Economics and Fashion Merchandising and has been featured in various industry publications for her contributions to retail and e-commerce. She sits on the board of directors for the Boca Raton Chamber of Commerce. Outside of her professional life, she is a passionate advocate for women’s empowerment and is actively involved in organizations that support this cause. She is dedicated to mentoring the next generation of female leaders. Sheryl’s journey in the fashion industry reflects her belief that style is not just about what you wear — it’s about how you live your life with confidence, authenticity and purpose.
Date: February 18, 2025
Credits: Sheryl Clark
Duration: 14:06
More Episodes
The Leadership Driving Fossil Group's Turnaround: A Chat With Brand Chief Melissa Lowenkron
In this episode of Women in Retail Talks, Women in Retail Leadership Circle Co-Founder Melissa Campanelli interviews Melissa Lowenkron, chief brand officer at Fossil Group, a global design, marketing, distribution and innovation company with a diverse portfolio of brands specializing in lifestyle accessories. They discuss how brands can grow during times of change. Lowenkron details why stepping into a chief brand role requires a mindset shift; how she leads the authentic storytelling that's key to Fossil's turnaround; her advice for leaders driving business transformations; and more.
22:39 How Lowe's is Building a Household Loyalty Ecosystem
In this episode of Women in Retail Talks, Women in Retail Leadership Circle Managing Editor Marie Albiges interviews Amanda Bailey, vice president of customer marketing and loyalty at Lowe's. This interview was recorded at Shoptalk in Las Vegas last month, where Bailey spoke on a panel exploring innovative approaches to marketing across the customer journey. Bailey discusses treating loyalty as a relationship beyond transactions; serving both DIY and pro customers via one loyalty platform with tailored benefits; building executive influence; and more.
22:06 Wayfair CTO Fiona Tan: 'Tech Leaders Should Plug Into the Business Side'
In this episode of Women in Retail Talks, Women in Retail Leadership Circle Managing Editor Marie Albiges interviews Fiona Tan, chief technology officer of Wayfair. This episode was recorded at Shoptalk in Las Vegas last month. Listen in as Tan discusses Wayfair's use of generative artificial intelligence and large language models; how she approaches new technology investments; and her advice for other female retail technologists who aspire to C-suite leadership roles.
17:27 CAMP CEO and President Jenica Myszkowski on Scaling Immersive Retail Experiences
In this episode of Women in Retail Talks, Women in Retail Leadership Circle Co-Founder Melissa Campanelli interviews Jenica Myszkowski, CEO and president of CAMP, an experience company that brings families together through immersive adventures that inspire play. This discussion was recorded at Shoptalk in Las Vegas last week. Myszkowski discusses how previous roles shaped her as a leader; overcoming challenges as CAMP scales and opens new stores; how she stays inspired and creative; and more.
11:27 Motivating Teams Through Radical Transparency: Insights From Lulus' CEO Crystal Landsem
In this episode of Women in Retail Talks, Women in Retail Leadership Circle Co-Founder Melissa Campanelli interviews Crystal Landsem, CEO of Lulus, the attainable luxury women's fashion brand known for trendy, stylish and feminine apparel, footwear and accessories. Landsem discusses the challenges and experiences that have informed her leadership style; her career journey from finance to fashion retail; motivating teams through radical transparency and servant leadership; her advice for young women leaders; and more.
20:54 RERUN: How BARK CXO Meghan Knoll Brings Storytelling to Dog Toy Design
In this episode of Women in Retail Talks, Women in Retail Leadership Circle Managing Editor Marie Albiges interviews Meghan Knoll, chief experience officer (CXO) at BARK, the leading global omnichannel dog brand known for its monthly subscription, BarkBox. Knoll provides an overview of her primary responsibilities as CXO, a few learnings from building the BARK business to where it is today, how she empowers her team to be innovative, her push-pull approach to work-life imbalance, and more.
40:09 Inside TOMS’ Turnaround: CCO Katie Wagner on Wholesale Growth and Brand Reinvention
In this episode of Women in Retail Talks, Women in Retail Leadership Circle Managing Editor Marie Albiges interviews Katie Wagner, chief commercial officer at TOMS, a Certified B Corporation global lifestyle brand known for its iconic shoes and giving model. Listen in as Wagner reflects on the first 20 years of the TOMS brand; balancing its iconic heritage with a brand refresh; lessons learned from her time at Crocs; creating a culture of curiosity; and more.
36:46 ButcherBox Commercial Chief Reba Hatcher on 'Mastering the Spin' in Career Transitions
In this episode of Women in Retail Talks, Women in Retail Leadership Circle Managing Editor Marie Albiges interviews Reba Hatcher, chief commercial officer at ButcherBox, a delivery subscription service that offers high-quality, humanely raised meat and seafood. Hatcher shares insights about ButcherBox’s evolution over 10 years; using data to achieve growth while staying connected to customers; her varied, nonlinear career trajectory; advice on navigating cross-industry career changes; and more.
32:41 Rothy's CEO Dayna Quanbeck on Growth and Credibility Rooted in Sustainability
In this episode of Women in Retail Talks, Women in Retail Leadership Circle Co-Founder Melissa Campanelli interviews Dayna Quanbeck, CEO and president of Rothy's, a direct-to-consumer company which takes a whole-brand approach to sustainability in manufacturing, transforming recycled materials into shoes, handbags and accessories. This episode was recorded at the National Retail Federation Big Show in New York City last week. Listen in as Quanbeck shares how Rothy's evolves while maintaining core values; what strong executive credibility looks like; lessons from her mentor, friend and former Rothy's CEO Jenny Ming; and more.
21:29 Boden Commercial Chief Katherine Danneberg Taps Into Her Leadership Purpose as an Enabler of Creativity
In this episode of Women in Retail Talks, Women in Retail Leadership Circle Co-Founder Melissa Campanelli interviews Katherine Danneberg, chief commercial officer at Boden, the quintessentially British clothing brand for women and children. Listen in as Danneberg explains the evolution of her leadership style, her leadership purpose, hiring the right team members to fit Boden's brand values, strategies for developing future leaders, and more.
25:51 
Apple Podcasts
Spotify
YouTube Music
Amazon Music
Pandora