As eCommerce reshapes the retail world, Harley-Davidson—a brand steeped in tradition and heritage—is exploring new ways to innovate and connect with customers. Kim Jackson, the Director of eCommerce at Harley-Davidson, recently joined the Happy At Work podcast to discuss the brand’s eCommerce strategy and how authenticity plays a crucial role in building trust with customers and within her own team.

The Happy at Work podcast explores the intersection of organizational culture, positive psychology, and employee branding to create thriving workplaces.

Dive into our conversation on Harley-Davidson’s eCommerce Evolution!

A Career Built on a Passion for Retail

Jackson’s journey to becoming the Director of eCommerce at Harley-Davidson is one marked by extensive experience in retail, from merchandise buying at Talbots to leading eCommerce efforts at Puma, Alex and Ani, and J. Jill. “I’ve always been obsessed with watching people shop and understanding what they do,” Jackson explained. This curiosity has driven her across multiple leadership roles, giving her a breadth of experience that she now brings to Harley-Davidson. Today, she is leading the company’s new initiative—HD Collections, an apparel concept that aims to reach beyond Harley’s traditional motorcycle enthusiasts.

Her time at brands like Puma and J. Jill helped Jackson understand the nuances of blending online and offline retail experiences. “When I moved to Puma, eCommerce was just starting to bud, and it was an incredible opportunity to explore how to engage consumers through new online channels,” she noted. At J. Jill, Jackson transitioned from creating assortments to focusing entirely on selling them online, which opened her eyes to the power of data and digital storytelling. “It was a whole new data set for me, a different way of looking at how we tell stories to our customers,” she added.

The Importance of Culture and Authenticity

Jackson’s experiences have made her a strong advocate for finding the right company culture—one where authenticity is valued. “For me, authenticity is key. Anytime I’ve tried to adjust how I lead or how I work with others to fit into a culture that wasn’t aligned with who I am, it has been a fail,” Jackson explained candidly. Finding a company culture that aligns with personal values is a cornerstone of Jackson’s professional success and is advice she regularly imparts to younger professionals.

Jackson described how important it is for companies to create an environment where team members feel empowered to make decisions. “If a person isn’t making a move because they are afraid their manager won’t like it, that’s when creativity is squashed,” she said. Her management philosophy is based on empowerment: “If there’s not a distinct risk to the business, I go with my team’s ideas 99.9% of the time because now they’re invested in the outcome.” This belief in empowering team members, allowing them to take risks, and supporting them even when things don’t go as planned is central to how Jackson builds trust within her team.

Navigating Harley-Davidson’s eCommerce Evolution

Harley-Davidson, a company that is synonymous with freedom, adventure, and the open road, has always had an incredibly loyal customer base. As Jackson pointed out, it is one of the most tattooed logos in the world. “Even if you don’t ride, there is something about the spirit of Harley-Davidson that resonates,” Jackson noted. This brand loyalty is a huge asset as the company expands its focus beyond motorcycles to include high-quality apparel that appeals to a broader audience.

Jackson is currently leading the charge on HD Collections, a new eCommerce initiative that launches in March. “This is all about extending Harley-Davidson’s brand affinity beyond just motorcycles,” she said. The project consists of three distinct apparel lines:

• High Fashion: Launched during Fashion Week, this collection takes the high-quality leather Harley is known for and reimagines it as lifestyle fashion.
• Originals: This line modernizes traditional Harley logos and styles, using contemporary fabrics and designs to appeal to today’s consumers.
• Authorized Vintage: Featuring curated pre-loved products, Authorized Vintage offers a nostalgic nod to Harley’s storied past, combining authenticity with exclusivity.

“It’s a high-touch, high-storytelling initiative, and it’s designed to include more people who may not own a bike but really love the spirit of what Harley-Davidson has to offer,” Jackson explained. The initiative includes collaborations with influencers and designers to further expand the brand’s reach.

Building Trust and Empowering Teams

Jackson emphasized the role that culture and support play in achieving success. She shared an anecdote from her early days at Harley-Davidson that underscored the collaborative nature of the company’s culture. “I was barely two weeks in when I had to present the HD Collections line to the CEO,” Jackson recalled. “I didn’t even know the people I was working with very well, but my chief digital officer assured me: ‘This presentation will be built for you. People will walk you through their parts, and we got you.’ That level of support made me feel like I was part of the team from day one.”

The company’s remote-first policy has also helped level the playing field, according to Jackson. “We’re all on the same playing field now, and that sense of equality has fostered a new level of collaboration and transparency,” she said. With the decision to go 100% remote, Harley-Davidson has not only embraced the future of work but is reimagining its physical spaces in Milwaukee to give back to the community, creating new opportunities for engagement.

Embracing Agility Over Perfection

One of the key cultural tenets Jackson and her team embrace is the notion of “done is better than perfect.” In a retail environment that is constantly changing, agility is critical. “We move fast, and getting something done is more important than getting it perfect the first time,” Jackson said. This mindset has allowed Harley-Davidson’s eCommerce team to remain nimble and responsive to new challenges, whether it’s launching new collections or addressing customer needs.

Advice for the Next Generation

As a mentor to young professionals, Jackson is passionate about sharing the lessons she has learned along the way. Her key piece of advice is to understand that career growth is rarely linear and that resilience is key. “I’ve been laid off, I’ve been let go, I’ve made mistakes,” Jackson said. “But I learned from every one of those experiences. You have to look at yourself in the mirror every day and like what you see. When you mess up, that’s your chance to fix it.” She also encourages people to be proactive in their learning and development. “You are responsible for your own growth,” she said, emphasizing the importance of seeking out opportunities and not waiting for them to come to you.

Jackson’s journey—from an assistant buyer to the Director of eCommerce at one of the most iconic brands in the world—serves as an inspiring reminder of the importance of staying true to yourself, continuously seeking opportunities, and fostering a culture of collaboration and trust. As Harley-Davidson continues to expand into the digital space, it is clear that the company’s focus on authenticity and empowerment will remain central to its strategy, both in how it serves its customers and in how it supports its employees.