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. 

Ken Pilot interviews Alex and Mike Faherty, co-founders and leaders of eponymous apparel brand, Faherty for this episode of The Retail Pilot. Alex is a co-founder and CEO at Faherty. Prior to starting at Faherty, Alex spent over a decade in Investment Banking and Private Equity. Formerly a football player at Yale, Alex takes a coaching mentality in how he runs the business, knowing that so much of a brand's success is who makes up the team. When he has time, and isn't coaching T-ball, he likes to surf.Mike wrote his college essay about starting Faherty Brand, going on to major in Fashion Design at Washington University in St. Louis before spending a decade in New York’s fashion industry. His passion is sourcing high-quality fabrics from around the world and developing innovative new ones himself. Mike loves playing basketball and finding off-the-beaten-track surf spots and restaurants. Key Highlights:1. Faherty has had a successful business with Australian tourists in the States, as the brand resonates well with English-speaking customers. They're planning to expand further, starting with a partner in Australia.2. Retail store growth is seen as a valuable way to capture customers, as it allows them to experience the brand in person and make a more significant commitment to the higher-priced products.3. The founders emphasize the authenticity of retail stores, as customers can't be deceived by appearances, and they have to genuinely like the products.4. Faherty is focused on finding unique, interesting locations for its retail stores, rather than following a cookie-cutter approach. They look for underserved areas with potential customers.5. Catalogs have been an important acquisition channel for Faherty since 2015. They are looking to evolve the catalog experience to stand out and feel more like a magazine or coffee table book.6. Faherty is shifting its approach to social media, aiming to create platform-specific content for various channels. They recognize the need to adapt to changing social media trends.7. The founders discuss their tech stack, highlighting platforms like Shopify for e-commerce and New Store for POS. They also use NetSuite for ERP and have implemented in-house tech solutions for design and development.8. Faherty is exploring how AI can enhance the customer experience, especially in terms of managing inbound and outbound communications efficiently.9. One of the challenges for Faherty is ensuring that as the brand grows, it still feels intimate and special to consumers, rather than becoming too corporate or generic.10. Mike emphasizes the importance of refining the sampling process using AI to ensure that only the most promising designs move forward, reducing sample expenses. 

Ken Pilot interviews Jan Singer about her incredible career as a Retail and Fashion leader and Board Member.Diverse Journey in Retail and Fashion: Jan Singer's career journey spans across various categories of business, not limited to retail. She's worked in luxury goods, beauty, and manufacturing for brands like Chanel, Calvin Klein, Prada, and Nike. Her experiences ranged from innovation to manufacturing and wholesaling.Initiating Career at Chanel: Jan shared an interesting story about how she found a phone number for Chanel, called in, and ended up speaking with the president, which ultimately led to her landing a job at Chanel.Challenging and Rewarding Leadership Roles: Jan believes that every job she's had has been challenging, and she's always been open to pushing herself to learn and grow. She mentioned navigating the 08 crisis at Nike as one of the most challenging moments. Additionally, running global footwear and apparel at Nike was a masterclass in leadership.Qualities as a Leader: Jan emphasized the importance of generous leadership, being an energy giver, and leading with optimism. She also talked about the value of being an enterprise leader, making complicated things simple and repeatable, and considering the broader perspective beyond her own space.Approach to Shaping Leadership Teams: Jan's approach to building a leadership team involves deep curiosity about why she's being brought in, understanding the problems the team is facing, and finding the critical few things that will make a difference. She values competency, chemistry, and balance in her teams, and is open to both internal and external talent.Dynamic Nature of Retail: Jan Singer highlights the dynamic nature of the retail industry. She emphasizes that no single company has everything figured out, and various aspects like channel dynamics, wholesale, direct-to-consumer, and digital interactions are constantly evolving.The Importance of Physical Stores: Jan Singer believes that stores are not dead; instead, they are evolving. She expresses her belief in the value of real estate, mentioning that stores are still crucial, but they might have shifted from malls to Main Street or open-air formats.Retail as Therapy: Jan Singer sees retail as a form of therapy for consumers. She believes that the engagement with shopkeepers, store staff, or online customer service fulfills a human need for connection and interaction. People shop for various reasons, and it can be a positive and uplifting experience.The Significance of Knowing the Consumer: Jan Singer emphasizes the importance of brands truly knowing their consumers. She mentions brands like Gucci that excel at understanding their customers' preferences and providing personalized services, whether through in-store interactions or online communications.Technology and the Future of Leadership: The discussion touches on the evolving role of CEOs in the retail industry. Jan Singer suggests that the skills required today may be so diverse that a single CEO might not be sufficient. She speculates about the possibility of a collaborative leadership structure involving operations, technology, and product leadershipOverall, Jan Singer provides valuable insights into the retail industry, highlighting the need for adaptability, personalized experiences, and a balanced approach to leadership in today's rapidly changing landscape.

Join Ken Pilot as he speaks with Co-Founder and CEO of Rhone, Nate Checketts, about his menswear business focused on fitness, comfort and everyday wear.Prior to Rhone, Nate worked for and consulted with some of the biggesttechnology and entertainment properties in the world including Cisco, The NationalFootball League, Legends, FanVision and Sport Radar. Nate is also an avid entrepreneur who founded and launched 4companies before the age of 30, including Rhone and Mangia Technologies, whose patents were later acquired by the San Francisco 49ers. In 2020 Nate was selected by the Sports Business Journal to their 2020 list of Forty leaders under Forty.In addition to Rhone, Nate also serves as Chairman of the Board to Beyond Type 1, a non-profit dedicated to the community of those with Type 1 Diabetes. Nate graduated from Brigham Young University with a BA in Finance. He and his wife Dayna reside in Connecticut with their three young boys, Gabriel, William and Nicholas.About Rhone was founded in 2014 by brothers Nate & Ben Checketts. Rhone is a premium men's wellness brand that creates best in class performance-driven apparel that is engineered for an active lifestyle. Rhone is dedicated to using their platform and products to address and discuss the complex issues that modern men face. From raising awareness around the mental health crisis, to building mutually supportive communities, to providing men with practical tools and resources to navigate relationships, Rhone seeks to support men while providing them with versatileclothing for every aspect of their daily routine. Currently, Rhone has more than ten retail stores across the U.S., all of which are used for building community through various initiatives such as the brand's signature Mind & Muscleevents. Rhone is also sold in all Equinox locations, and available nationwide at Nordstrom, Bloomingdale’s, Dillard’s, SCHEELS, select CorePower Yoga locations, and more than 350 gyms and specialty stores across the country. Rhone is also a proud partner of Stitch Fix. More information can be found at www.Rhone.com.Key Highlights Include:Rhone's Origin and Vision: Rhone, a men's performance lifestyle brand, was founded with a vision to fill a void in the men's fashion space. The founders, including Nate Checketts and his brother Ben, aimed to create a brand that offered high-quality, versatile, and high-performance clothing that could be worn in various settings, blurring the lines between work and leisure attire.Balancing Family and Business: Nate and his brother Ben, along with their brother-in-law, founded Rhone as a family venture. They emphasize that working together as a family has been a positive experience, and Ben's interest in clothing design complemented Nate's entrepreneurial background.Omni-Channel Approach: While Rhone began as an e-commerce brand, it recognized the importance of an omni-channel approach. They expanded into physical retail stores, selecting high-end partners like Equinox to offer their products. This strategic move allowed them to meet customers where they were and helped them gain recognition in the market.Retail Expansion and Profitability: Rhone currently operates 15 retail stores, and they prioritize profitability over rapid expansion. They are careful in selecting wholesale partners, ensuring that the brand is represented appropriately. All of their stores are profitable, which has provided a strong foundation for future growth.Future Growth and Product Expansion: Rhone is exploring opportunities for growth, including potential expansion into the international market. They are also considering product line extensions, including potentially re-entering the women's market. However, their primary focus remains on delivering exceptional quality products and ensuring the customer's experience is at the forefront of their decisions.Investor Criteria: The company looks for investors who can bring value in three key areas:Reputation: They prefer investors with a notable name that they can leverage for credibility.Network: Investors who can make valuable introductions to other influential individuals.Expertise: Those who can offer valuable insights and advice when needed.Navigating Challenges During COVID: The COVID-19 pandemic brought both business and personal challenges. Managing the business crisis while also dealing with the human crisis was particularly difficult. It led to burnout and a realization that changes were needed.Growth and Transformation: Bringing in experienced executives who have successfully navigated company growth from smaller to larger stages was transformative for the business. This allowed the CEO to focus on their strengths and enabled the company to scale effectively.Focus on Mental Health: The brand's commitment to mental health has been a core part of its mission from the start. They recognize the unique challenges that men face in seeking and receiving mental health support. They've integrated physical activity with group therapy sessions to create a supportive community.Innovation and Technology: The company embraces technology as an enabler and is particularly interested in advancements related to customer data, retail analytics, and AI-driven customer service enhancements. They're using technology to gain a comprehensive view of their customers and to optimize their operations.

In this Flight of The Retail Pilot - Leaders & Legends, Ken speaks with Sharon Leite, CEO of Ideal Image, former CEO of The Vitamin Shoppe and Retail Leader at companies such as Gap, Bath and Body Works and Pier 1. Key Takeaways of the Episode:* Passion and Connection to Mission: Sharon emphasizes that passion for the business, brand, product, and mission is more important than monetary compensation. Connecting personally with your work is crucial for long-term success.* Career Stages and Growth: Sharon's career evolved through three distinct stages: learning the business and consumer experience, turning around businesses, and applying her knowledge to legacy brands. Each stage contributed to her growth and success.* Due Diligence and Understanding: Sharon learned the importance of thorough due diligence when considering new opportunities. Understanding the company, industry, and board's vision is essential for a successful and fulfilling career.* Surrounding Yourself with the Right Team: Building a team that shares the vision and understands what excellence looks like is crucial, especially in situations requiring rapid change or turnaround. Having the right people in the right roles accelerates progress.* Transforming a Business: Sharon's experience at the Vitamin Shoppe highlights the significance of rebranding, understanding the customer, telling compelling stories, and aligning with industry experts. This transformation ultimately led to success despite the challenges presented by COVID-19.* Adaptation during COVID-19: The Vitamin Shoppe faced challenges during the COVID-19 pandemic. She had to fight to reopen their stores, and what allowed her to do so was a focus on selling essential items like food, functional foods, and water.* Preparation paid off: Before the pandemic, the company had made strategic investments in e-commerce, technology, and loyalty programs. This preparation proved crucial, as they didn't have to scramble to implement services like online pickup, curbside pickup, etc., when COVID-19 hit. This readiness accelerated their growth during the pandemic.* Leadership through presence and celebration: Sharon emphasized the importance of showing up, especially during tough times. She visited distribution centers, stores, and events, creating a celebratory environment within the company. This approach helped foster a sense of appreciation and connectedness among the team.* Transition from public to private company: Sharon’s company transitioned from being a public to a private company. This move allowed her to focus on long-term business improvements without being beholden to short-term investor expectations.* Reimagining Ideal Image: Recently, Sharon transitioned to a new company, Ideal Image, with the goal of building a comprehensive women's lifestyle brand in beauty, health, and wellness. She plans to reimagine various aspects of the business, including services, culture, products, and market leadership. She also hinted at a potential move into health and wellness.

Throwing it back to the second episode of The Retail Pilot, join your host Ken Pilot, as he continues the conversation with Millard "Mickey" Drexler, Retail visionary and Chairman of Alex Mill.Come along for the ride as Ken and Mickey chat more about Mickey's legendary career building brands and his legacy with leading companies such as Ann Taylor, Gap, Old Navy, J.Crew, Madewell and now Alex Mill.If you enjoyed this episode of The Retail Pilot, please let us know by subscribing to our channel and giving us a 5 star rating on Spotify and Apple Podcasts!

Throwing it back to the debut episode of The Retail Pilot, join your host Ken Pilot, as he embarks on an inspiring conversation with none other than Millard "Mickey" Drexler, the visionary Chairman of Alex Mill.Buckle up as Ken and Mickey delve into the riveting tales that have shaped Mickey's illustrious career, leaving an indelible mark on the retail landscape. From his groundbreaking endeavors at Ann Taylor, Gap, and Old Navy to his iconic stewardship at J.Crew, Madewell, and now Alex Mill, Mickey's story is a testament to innovation, perseverance, and unmatched expertise.If you enjoyed this episode of The Retail Pilot, please let us know by subscribing to our channel and giving us a 5 star rating on Spotify and Apple Podcasts!

Join your host Ken Pilot in this episode of The Retail Pilot, as he sits down with Marc Metrick, the driving force behind the transformative journey of luxury retail giant Saks Fifth Avenue. From his early days at Saks to his pivotal role in the acquisition and integration of the iconic brand, Marc takes us through a captivating tale of strategic evolution and reinvention.Learn how Marc's visionary leadership led to a critical juncture in 2019, as Saks embarked on a groundbreaking split into two distinct entities. He unveils the motivations behind this move, detailing the challenges and opportunities it presented. Marc's insightful narrative shines a light on the redefined hierarchy of KPIs, talent acquisition, and resource prioritization that formed the bedrock of Saks' digital-first transformation.Marc's unique perspective on owning the IP, controlling pricing and promotion, and the symbiotic relationship between the e-commerce and stores arms of Saks will leave you with a deep appreciation for the intricacies of luxury retail management. Join us as we dive into Marc Metrick's journey, unveiling the secrets behind Saks Fifth Avenue's evolution into a modern-day retail powerhouse. If you enjoyed this episode of The Retail Pilot, please let us know by subscribing to our channel and giving us a 5 star rating on Spotify and Apple Podcasts!

Their story began in the offices of Sam & Libby Shoes, a modest footwear brand in California. John Edelman, working alongside his brother Sam, crossed paths with John McPhee, igniting a friendship that would set the stage for an indelible partnership. In their candid discussion on The Retail Pilot, the two Johns share the story of their humble beginnings, recounting how a casual dinner invitation would eventually reshape the design landscape.Their collaborative efforts led them to Edelman Leather, a family business they nurtured into a multi-million-dollar success, later acquired by Knoll. The challenges didn't stop there. Together, they took on the ambitious task of revitalizing Design Within Reach. Against all odds, Edelman and McPhee orchestrated a remarkable turnaround, proving that dedication and strategic thinking can redefine a brand's identity.Tune in as the Johns recall their pivotal moments, from facing skeptical employees to forging relationships with international vendors. Learn how their enduring partnership reflects their shared values and commitment to exceptional design. Plus, tune in to discover their life now as John Edelman is President & CEO at Heller and John McPhee is CEO and Chilewich.

Join us in this inspiring episode as Ken sits down with Joey Zwillinger, the Co-founder & CEO of Allbirds, the groundbreaking footwear brand that's taking the world by storm. From humble beginnings to a global sensation, Allbirds has redefined the way we think about shoes, combining style, comfort, and sustainability in a way that's never been seen before.In this candid conversation, Joey takes us on their remarkable journey, sharing the challenges he faced as they disrupted the traditional footwear industry with their eco-friendly, renewable materials and commitment to reducing their carbon footprint. Ken and Joey delve into the early days of Allbirds, from the spark of an idea to the inception of a brand that has now become a symbol of sustainable fashion.Learn how they navigated the ever-changing world of fashion and e-commerce, adapting to evolving consumer preferences while staying true to their brand values. We'll also discover the pivotal moments that shaped their company and the values that continue to guide their decisions.Listen now and explore the inspiring journey of Allbirds, a brand that proves that style, comfort, and sustainability can go hand in hand, revolutionizing the way we walk through life.