The Retail Pilot

1.    Todd Snyder's Background: Todd Snyder, a retail designer, grew up in Ames, Iowa, with a background in business. Despite his unconventional path, his passion for clothes and fashion ultimately led him to pursue a career in design.2.    Early Fashion Influences: During his high school years, Todd admired designers such as Calvin Klein, Ralph Lauren, and Armani. However, as he transitioned into college and began working in retail (particularly selling Ralph Lauren's Polo clothing), his admiration for Ralph Lauren's work grew, solidifying his aspiration to become a designer.3.    Early Retail Experience: Todd gained valuable experience in the retail industry, working at various stores in Iowa, including Yonkers and The Buckle. He also worked in a store called Bedowers, where he not only sold menswear but also worked in the tailor shop, sparking his interest in the process of creating clothing.4.    Internship at Ralph Lauren: Todd's first significant step into the fashion industry was through an internship at Ralph Lauren. As an intern, he took on various tasks, ranging from fetching coffee to organizing the closet. This experience allowed him to make a positive impression and eventually led to freelance opportunities with the company.5.    Transition to J.Crew: In 1993, Todd transitioned to J.Crew, a pivotal time for the company's growth. While at J.Crew, he contributed to the development and expansion of the business.6.    Challenges of Running a Business Solo: Todd shares the difficulties he faced while self-funding his business, highlighting the limitations of personal credit and the need for external investment. He reflects on the pivotal moment when American Eagle approached him, providing an opportunity for growth.7.    Transition from Wholesale to Direct-to-Consumer: Todd discusses the evolution of his business model, emphasizing the shift from primarily wholesaling to being almost entirely direct-to-consumer. He explains the challenges he faced with wholesale, such as differing seasonal schedules and SEO competition, and the benefits of focusing on direct customer engagement.8.    Diverse Product Assortment and Customer Segmentation: Todd emphasizes his commitment to offering a wide range of products, from sweatshirts to tuxedos, to create a one-stop shopping experience for men. He also shares insights on customer segmentation and the importance of effectively managing a growing customer base.9.    Marketing Strategies: Todd discusses the various marketing channels he utilizes, including influencer collaborations, affiliate partnerships, and social media advertising. He highlights the shift towards mobile-focused advertising and the challenges posed by recent iOS changes10. Embracing Technology for Customer Engagement: Todd reveals his interest in implementing AI-driven tools to enhance customer experience. He expresses the importance of using technology, like CRM systems and AI, to predict and cater to customer preferences, providing a personalized shopping experience.Hosted by Ausha. See ausha.co/privacy-policy for more information.

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. Hosted by Ausha. See ausha.co/privacy-policy for more information.

Alex and Mike Faherty discuss their journey from passion to brand, revealing the importance of authenticity in retail. They share insights on building a positive work culture and the thrill of making personal connections with customers. The brothers highlight their innovative sourcing practices and plans for strategic growth in women's apparel. With a focus on embracing technology, they delve into evolving social media strategies and the role of AI in enhancing customer experiences. Their story reflects a blend of creativity, collaboration, and commitment to ethical fashion.

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.Hosted by Ausha. See ausha.co/privacy-policy for more information.

Nate Checketts, Co-founder and CEO of Rhone, discusses his journey in creating a men's athleisure brand that blends style with comfort. He shares insights on navigating retail dynamics and the importance of strategic partnerships. The conversation also highlights the mental health challenges men face and how Rhone fosters community support. Checketts dives into innovative fabric technology that combats odors and reflects on the significance of quality and storytelling in marketing. A light-hearted rapid-fire segment provides fun personal anecdotes.

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.Hosted by Ausha. See ausha.co/privacy-policy for more information.

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!Hosted by Ausha. See ausha.co/privacy-policy for more information.

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!Hosted by Ausha. See ausha.co/privacy-policy for more information.

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!Hosted by Ausha. See ausha.co/privacy-policy for more information.

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. Hosted by Ausha. See ausha.co/privacy-policy for more information.