Ken Pilot interviews Sheryl Clark, CEO & President of Boston Proper, a best-kept secret for women over 40, designing unique, on-trend, high-quality fashion for every occasion. Sheryl’s experience includes time at Bloomingdales, Gap and Old Navy prior to joining Boston Proper.

Key highlights of the interview are:

Sheryl's Background and Career Journey: Sheryl shares her background, growing up in an Italian immigrant family, and her early fascination with clothing. She discusses her education in business economics and fashion merchandising, as well as her start in the Bloomingdale's executive training program.
Career at Gap Inc.: Sheryl talks about her time at Gap Inc., including her experiences at Bloomingdale's and the Gap. She highlights a pivotal moment when she took on a VP of men's position, demonstrating the importance of being open to new opportunities.
Transition to Old Navy: Sheryl discusses her transition to Old Navy, where she played a significant role in the brand's growth and success. She emphasizes the importance of key items and marketing in differentiating the brand.
Challenges and Growth at Boston Proper: Sheryl shares her decision to leave Gap Inc. and join Boston Proper as CEO. She reflects on the challenges and changes the company underwent, including a sale to Chico's and a subsequent transition to private equity ownership. She also introduces the concept of "Lucy," the brand's target customer.
Future Plans and Strategies: Sheryl outlines the three pillars of Boston Proper's growth strategy: shifting from catalog-focused to customer-focused, enhancing customer experience, and going digital. She also announces the upcoming launch of the Miracle marketplace, which aims to expand the brand's assortment and reach new customers.
Marketplace Strategy vs. Pure Wholesale: Sheryl Clark discusses Boston Proper's interest in utilizing the Miracle Marketplace Network rather than pure wholesale due to margin considerations and the need to refine their sourcing strategy.
Transition to Digital: Sheryl emphasizes the brand's shift towards digital, acknowledging the challenge of transitioning a 30-year-old catalog-centric culture to a digital-focused approach.
Introduction of a Loyalty Program: Sheryl mentions the launch of Boston Proper's first-ever loyalty program with Yap-O, aiming to increase customer frequency and average order value.
Technological Advancements: Sheryl outlines the adoption of various technologies to enhance customer experience, including Publitas for digitizing the physical catalog, Gorgias for customer service, and exploring shoppable video platforms like Firework.
Marketing Shift Towards Digital: Sheryl discusses the evolution of Boston Proper's marketing strategy from predominantly catalog-based to allocating over 50% of marketing spend on digital channels. She highlights successful ventures into OTT advertising and podcasts with iHeartMedia.

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