The Digital Stronghold
Stephen Henderson is an accomplished executive with extensive experience in digital commerce and marketing. Currently serving as Chief Executive Officer at The Digital Stronghold since May 2023 and Operating Partner at Digital Fuel Capital since November 2022, Stephen has a proven track record in leadership roles across various prominent companies. Previous positions include Chief Digital Officer at Cole Haan, SVP of Marketing & eCommerce at Caleres, Inc., and VP Direct to Consumer at Coty. Stephen's career also features significant roles in eCommerce and digital strategy at Payless ShoeSource, Arc, and The Sak. Academically, Stephen holds a Master of Science in Strategic Design and Management from Parsons School of Design and a Bachelor of Business Administration from Golden Gate University.
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The Digital Stronghold
The Digital Stronghold is a multi-brand platform supporting leading digitally native men’s apparel, accessories and grooming brands in accelerating their growth. Our brands include Taylor Stitch, The Tie Bar, and Boston Scally. We exist to create an environment for men’s interest brands to thrive together. At the heart of our belief is that when you have shared learnings, shared services and shared centers of excellence you are able to create something that propels both growth and profitability. In short, we are better together. We exist to be a support system for the brands so they can focus on the things they are best at and love the most. We have seen first hand what adding amazing shared services around finance/accounting, digital marketing, digital product, operations and logistics can do to make a brand breakthrough to grow faster and become more profitable. We believe each brand and the products within those brands are unique and should stay that way. We don’t want to control the brand, messaging or product. We want to exist quietly in the background helping our brands build the best experience possible for their customers to strengthen the genuine bond between a community of customers and the brand. We believe in sustainable and responsible growth. Brands who try to grow too fast generally lose a connection with their customers and lose focus on the importance of building great product. Of course we love to see growth but we don’t want to see that at the expense of brand and product integrity. If you’re an amazing brand, we’d love to have you join us. If you’re a customer, we’d love to hear from you.