For Andrew Benka, his role of Chief of Staff to the CEO and VP of Product Management at Harley-Davidson, is not just a job but a way to channel his lifelong attachment to the brand. He talks to Al Clarke, Chairman of the Ennis & Co Advisory Group, about leadership and living the dream.
You’ve built your career at Harley-Davidson across a variety of functions – operations, marketing, developing international markets, and now as Chief of Staff and VP of Product Management. What drew you to Harley-Davidson, and what has kept you committed to the brand?
My connection to Harley-Davidson goes right back to my childhood. Both my grandfathers were linked to the brand. On my father’s side, my grandfather was a Milwaukee County sheriff’s officer who rode a Harley. My grandfather on my mother’s side was an entrepreneur whose company eventually became Harley’s biggest chrome plater. As cheesy as it sounds, I feel like it was my destiny to end up at Harley.
I grew up in Chicago, studied in Milwaukee and worked at KPMG in audit, mostly with manufacturing clients. This in itself meant that Harley was always on my radar. When a recruiter then reached out about a finance position with the brand, everything seemed to come together and align perfectly in that single moment.
I’ve been riding since I was 16, and my grandfather’s network helped foster that. I’m approaching 31 years at Harley and, for me, it’s more than a job. It’s a personal, emotional bond with the brand.
Can having such a close connection with the brand be a risk as well as a strength? Does it ever make you blind to business realities?
That’s an interesting point. I hope not. I think my business acumen and judgment shine through those moments, even when I’m deeply connected. Harley hasn’t had a completely smooth journey over the past 10 to 15 years, which has made me even more curious and determined. If anything, this bond makes me more acutely aware of challenges and opportunities rather than blind to them because I’m so invested in seeing things succeed.
Tell me about your journey from finance to Harley. Was it the specific role that most attracted you or the brand?
Joining Harley-Davidson was really about the brand. I was aware of the emotional connection even then, thought it was latent. I’ve always been both left and right-brained, and I started in corporate accounting knowing I had more to give. I never had a five-year plan. I just focused on doing my best in each role, trusting that would take care of itself.
A major milestone came in the early 2000s when I moved to the UK to help establish the financial planning department. That experience opened my eyes to the diversity of Harley’s markets while still seeing the consistency of the brand globally.
After returning to Milwaukee, I transitioned into strategic planning, and then took a leap into a very unconventional role: I ran a snowboard, skateboard, BMX and motocross shop for four years to test a potential business model. In reality, it was an ethnographic research assignment – understanding young people’s openness to risk and their potential connection to Harley motorcycles. The COO at the time warned me that this move would end my finance career, but I knew I had more to give than finance alone.
It turned out to be a pivotal experience, and I learned an incredible amount about people, operations and market dynamics. Before this, we were fifth in market share with young people. Afterwards, we made product and marketing moves that helped us reach number one. From there, I moved into consumer insights, marketing and back into strategy, eventually taking on highly accountable regional leadership roles in EMEA and AMEA.
These experiences were breakthrough moments, moving me from back-office finance into front-line, high-impact leadership. Each step built on the previous one, combining analytical skills, creativity and a deep understanding of the brand and its customers.
Did you map out your career direction early on, or have you tended to follow where intuition and opportunity have led?
For me, many decisions have been guided by intuition. My strengths don’t sit purely in finance or purely in creative. I’m somewhere in the middle, and I thrive in roles that allow me to bridge the two. I like bringing creative ideas to life in a business-oriented way, and that flexibility has been a real advantage.
I’ve also relied on trusted advisors. My sister, a highly successful executive director of a nonprofit, has been an incredible sounding board. Within Harley, I’ve had different voices guiding me. The COO once said a particular move was the worst decision of my life, while the VP of Strategy was a voice of good in that moment. They supported it and encouraged me to exercise my full capabilities.
Ultimately, the key is understanding what makes you great and maintaining a strong point of view. That internal conviction becomes your guiding light. If you’re not confident in yourself and your decisions, things rarely go well.
As one of the most senior leaders at Harley-Davidson, working closely with the CEO, how has your leadership style evolved over your career? What does your leadership look like today, and what skills are required to work closely with the CEO and manage stakeholders?
Early in my career, my leadership style was driven by sheer positive energy. I was perhaps a bit naive at time, and I wasn’t as focused on accountability. I tended to play more of a supportive role.
Taking on the EMEA role was a defining moment. It allowed me to combine the best parts of being a collaborative, positive leader with a sharp focus on results and accountability. At the time, it was the company’s second-largest region, and I inherited a challenging situation.
I quickly realised there’s no hiding when you lead a region. The problems are very visible. The advice I received from our Chief HR Officer was invaluable: ‘When you take a big regional role, you have one shot to build your team. Don’t rely on someone else’s. Build your own.’ I took that to heart, made significant changes and the first six months were turbulent. Once I navigated that period, we were able to get back on a path of growth. Building my own team and being accountable for results became central to my leadership style.
Moving from the mothership in the US to regional roles, was that a gamble for your career? How did you weigh the risk?
In a significant way, yes it was a gamble. My wife is a British citizen, so there were personal motivations that made the move seem natural, and ultimately it was worth the risk. Looking back, I’ve made a number of risky career choices but I tend to follow my instincts. If you keep delivering and ‘putting your nose to the grindstone’, as my father would say, opportunities for greater scope and responsibility tend to follow. My approach has often been to just take the leap. It may not be conventional, but sometimes you have to jump.
Do you think leadership styles changes as you rise higher in an organisation?
Yes, absolutely. Having served as Chief of Staff under three CEOs, I’ve learned to think like a CEO. It’s almost a yin-yang relationship. The best chiefs of staff complement the CEO rather than mirror them, which helps influence the organisation and drive the CEO’s strategic agenda.
Collaboration becomes a critical leadership attribute. As COS, you often operate as a lone wolf, so influence is key. Command-and-control approaches don’t work well in this role, and highly collaborative and influential leadership is far more effective. My history within Harley-Davidson has also made influencing easier, giving me the credibility to move the organisation forward while supporting the CEO’s agenda.
Does having experience across multiple functions and regions within Harley-Davidson give you more credibility and influence as Chief of Staff compared to someone coming in from outside?
Absolutely, My experience across regions, product and finance uniquely qualifies me and gives me the credibility to influence at peer level. There are different ways to approach the role – as an executive assistant to the CEO, as a programme integrator or as the CEO’s voice within the organisation. I’ve naturally gravitated toward the latter. That ability comes from the trust and understanding I’ve built over three decades at Harley-Davidson.
Having worked through both boom times and more challenging periods, I’ve learned to stay relentlessly positive and curious about what’s possible. Even after 31 years, I focus on solutions and the future rather than reasons things might not work, which I think helps the wider leadership team navigate change with optimism and confidence.
The Harley-Davidson mission is, ‘More than building machines, we stand for the timeless pursuit of adventure. Freedom for the soul.’ How do you embed that mission into the way the business operates internally throughout the layers of the business?
That mission statement is a lot more than just words on a wall. It’s about selling a dream, not just a product. Other mission statements we’ve had over the years have been equally emotive, like ‘fulfilling dreams of personal freedom’. To bring it to life as a leader and in recruiting future leaders, Harley-Davidson mandates high emotional intelligence. This isn’t a standard automotive company. We’re not just putting four wheels on a box. We’re selling someone a dream and the fulfilment of a lifetime’s hard work.
Leaders here need both high IQ and functional capability, but also depth of emotional capability – the ability to sell that dream authentically. I’ve received messages from people who say Harley has changed their lives, helped them rediscover who they really are. If you can’t resonate with that as a business leader, you won’t succeed at Harley, whether you’re in accounts payable or brand creative. Understanding the emotional texture of what we do is essential. Bill Davidson would say, ‘We’re not selling widgets, we’re selling dreams.’ If you’re not on board with that, you should probably go sell widgets somewhere else.
You’ve seen Harley-Davidson evolve over the years with initiatives like LiveWire, H-D Membership, and ‘The Hardwire’ strategic plan. How have these changes impacted you, your role and your leadership style?
Working for Harley-Davidson is iconic. We’ve long been seen as a leadership brand. Historically, though, the company hasn’t been known for taking risks or being comfortable with failure. That’s exactly where you have to be to grow. Harley is incredibly strong, and sometimes our greatest strengths can also be our greatest liabilities. Being so strongly defined can feel limiting.
If you dig deeper into the brand’s values, however, there’s real elasticity. Harley can, and should, stretch into new growth spaces. You have to be comfortable with losing, which isn’t in our traditional track record. Historically, we’ve been winners. My focus as a leader has been helping teams see Harley as an underdog story. For over 100 years, we’ve consistently fought uphill – through the Great Depression, economic downturns, world wars and even near-mismanagement under its AMF ownership.
Framing it this way – as a modern underdog story – allows us to maintain optimism during uncertainty and transformation. We’ve done new things before, and there isn’t a single formula for success. Embracing the brand’s elasticity, and creating optimism from our heritage, helps leaders navigate change while staying true to Harley’s identity.
Looking back on your career, what advice would you give to leaders stepping into senior roles today? What skills are most important for them?
Great question. We’re currently navigating a shift as employees return from remote work to the office, which has promoted reflection on what it truly means to be a Harley-Davidson employee. The word that consistently comes up in these conversations is family. You’re a part of the extended Harley-Davidson family, and that still holds true today.
I couldn’t imagine having a 31-year career at another company, but at Harley it’s possible. The culture allows you to bring your true self to work and be rewarded for it. Vulnerability is key. As a leader, showing who you really are – what drives you, where you seek perfection and where you don’t – builds trust, enhances performance and fosters longevity. It’s a reflection of our bikes too. Just as people customise them to show their personality, our employees bring their individuality to the business, creating a unique culture and sense of magic.
As for leadership style, it develops more naturally here. We’ve faced challenges over the past 15 years, particularly in creating continuous demand for a highly discretionary product sold on a dream. This has forced us to seek leaders with new capabilities in demand creation, creativity and brand cultivation while balancing passion with professional capability. Harley benefits from both: people with inherent passion for the brand and the functional skills to make an impact. The challenge is finding that balance. Enthusiasm alone isn’t enough but, combined with capability, it drives the organisation forward.
Because our challenges are cultural as well as industry-specific, we often look beyond the motorcycle sector for leadership talent. For example, our new CEO comes from the golf industry. My role is to help leaders from outside the industry understand the brand, its challenges and its culture, allowing fresh perspectives to thrive while respecting Harley’s heritage.
Do you think you could you ever work for another company? Could you bring that same passion?
It is a fascinating question. I would like to think I could but it would have to be place that is equally special. I couldn’t work for an ‘insert badge here’ type of automotive company, but if it was a company that heritage, brand, elasticity and momentum, then yes I could get wrapped up in the emotion of it. It couldn’t just be generic opportunity but would need to have texture. Brands should be like Velcro, with multiple attachment points. If a company offered that, I’d be all in.
Who have been your most influential mentors or leaders, and what made them so impactful?
A former Chief Commercial Officer played a pivotal role in my development, taking a gamble on me when I moved from a support role to operational leadership in EMEA. She was a highly accountable leader with a clear perspective on what it meant to lead a team, and I’ve carried much of her philosophy forward.
One of the biggest lessons she taught me was the concept of first team leadership – the idea that your primary team isn’t your direct reports but your peers. When leaders are fully invested in each other’s success, the whole organisation benefits. That mindset, coupled with her focus on accountability and talent, marked a breakthrough in my own leadership, transforming me from ‘Andy the creative guy’ into a regional leader capable of driving real performance.
Our relationship was a blend of mentoring, structured dialogue and formal training, and her discipline was extraordinary. Before I took on the role, she spent two hours setting expectations. She instilled a culture of accountability and collaboration rooted in principles drawn from the US military. At the time, her approach felt intense and demanding but, looking back, it created a lasting gear shift in how I lead and develop others.
Is there a price to pay for being a successful leader?
If you’re blessed enough to be in a highly functioning relationship alongside your career, you’ll know that stress is inevitable. It’s impossible to do all aspects of life effortlessly – to be fully committed to your career, maintain a relationship and have a family without feeling strain somewhere along the way. Something always has to give.
I’ve been incredibly fortunate to have a partner who’s been a real hero in my journey. She previously worked at Harley-Davidson and understood the brand’s emotional and lifestyle dimensions, which made her support all the more meaningful. But that doesn’t mean it’s been easy.
My advice, and something I often share with those looking to break through into a senior leadership role, is that you have to be prepared to go all in. Perhaps it’s a slightly dated perspective, but I believe it still holds true. The idea that you can ‘have it all’, the perfect Instagram life, isn’t real. There are real sacrifices that come with pursuing success at a high level, and both you and the people around you need to be open to that reality.
