There are many ways to lead and many paths to leadership. Whether it be along common routes mapped out by traditional and historically male-led institutions, or via more organic, values-driven approaches, the path to the C Suite can vary. To celebrate Women’s History Month we talked with one of our executives, Karen Stroup, Chief Digital Officer at WEX, about her career trajectory, the challenges and opportunities she has experienced, and how her own natural curiosity impacts her career.
Not all paths to the C Suite take a straight and narrow path
Karen’s evolution as a business leader didn't come from a desire to succeed for success's sake. Her ambition stemmed from a more intuitive interest in the world, and a desire to make an impact. “People ask me how I got to where I am and it certainly wasn't a straight line and it wasn't intentional. I never said I wanted to be a C-Suite executive. I've been driven by curiosity, problem solving, and the desire to make a difference. That culminated in larger roles, bigger opportunities and supportive mentors. It was as much good luck as hard work and ambition.”
In a business class as an undergraduate at Notre Dame, Karen was introduced to Boston Consulting Group (BCG). BCG's areas of focus were highly interesting to her. “I loved the idea of strategy and solving problems, and the curiosity of, ‘How do you grow? How do you solve customer needs? How do you differentiate yourself?’”
Graduating Summa Cum Laude with a BA in Finance and Business Economics, Karen started work in consulting, experiencing a period of growth. She focused on the customer experience, which fascinated her. “I worked in consumer packaged goods and retail where there's a focus on the customer. We followed the customer to the restaurant, we followed them home - with a goal of understanding their needs and their experience. By watching and talking with customers, how customer needs intersect with business strategy became clear. Where they're connected, where they're disconnected, what influences a customer’s decisions to buy a product, and why they’d most likely recommend it to others.” Karen’s early interest in the customer experience continues to guide her career.
Abstract lessons about leadership can come in surprising ways
Karen also discovered the value of getting comfortable with ambiguity, and developing her own curiosity about data in her earliest work experiences. Both were essential for success in consulting. “These projects were three or four months long, so as a 22-year-old, I had to jump in and immediately figure out how to distill a lot of information, identify the key questions to answer, create hypotheses, get comfortable with being wrong, and use data to drive decisions.” These learnings created the groundwork for a rich and dynamic career.
Immersion in the business of technology can reap major rewards
Earning an MBA at Dartmouth’s Tuck School of Business, Karen’s BCG job then took her to San Francisco where she further developed her skills and expanded her experience.The abundance of tech companies in the Bay Area pushed Karen into new areas, leading her to learn about technology and its impact on customers' experiences. “I fell in love with that intersection of customer and technology - deeply understanding the customer problem and using technology to reimagine new ways of doing things. Long-standing inefficiencies, things that waste our time or are frustrating – technology opened up better ways to create solutions to customer problems.”
Choosing an opportunity should be about growth, not title or pay
Instead of continuing in a space that was comfortable to her at BCG where she had built cachet and cultivated relationships, Karen expanded her knowledge and extended her expertise to other areas of business. “I left consulting because I wanted to move beyond strategy and learn how to execute and drive change in an organization.”
When exploring new opportunities, Karen said, “Throughout my career, I have never focused on the title or the money. It hasn't been about the number of people I manage. I’ve focused on finding growth opportunities that include great mentors.” She engaged in thoughtful leadership development processes, observing and studying great leaders, and focusing on her own skills and where self-improvement opportunities might exist. “What are the gaps in my own skills where I can improve? How will this opportunity help me build on that experience? Where can I gain more confidence in situations that are a little bit uncomfortable for me?” Leaving BCG, Karen looked for a company that would challenge her, had a strong culture, and was fun and supportive. This led her to Intuit and product management, both of which were new challenges for her.
Define what matters to you
The CEO at Intuit challenged every leader to define their own leadership philosophy. After much reflection about the strengths of various leaders she worked with, Karen identified key lessons she learned over the years and formed the core foundation of her leadership philosophy. This foundation has endured over the years.
Have a learning mindset
Karen has always been curious which she attributes in part to growing up in a household where curiosity was celebrated and cultivated. Her mother, who retired from teaching when Karen was born, spent her time encouraging Karen to learn about the world and ask questions. This curiosity developed into a consistent theme throughout Karen’s career.
Karen’s mentors throughout her career encouraged curiosity. Intuit’s CEO encouraged asking “Why” in a variety of situations. “He taught us to ask ‘Why’ repeatedly to get to the root cause.” Intuit also embraced customer-driven innovation, celebrating learning, not fearing failure, and translating those insights into successes.
It’s your responsibility to have a point of view and speak up
Sometimes it’s the obstacles we face that build the person we become, and for Karen the biggest obstacle in her early career was her lack of confidence. Coaching early on encouraged her to find her voice, speak up, and impact the conversation. She shed her misperception that because there were more senior people in the room, her perspective wasn’t important. “I got great coaching that while I might not be the senior person in the room, I was closer to the problem and data so my insights were valuable.” The biggest shift in thinking came with understanding that it was her responsibility to weigh in. It wasn’t just important for her own growth and development, it was important to the work at hand. Speaking up if there were inaccuracies in the discussion was difficult, but essential to making an impact.
Authenticity and leaning into your strengths leads to success
Karen was fortunate to work for many inspiring leaders with unique strengths and styles, often different from her own. For years, Karen felt that to be successful, she needed to emulate the styles of the people she worked for.
Karen was sharing her admiration for one particular colleague with a co-worker at a business dinner and experienced a paradigm shift in her thinking. “I tend to be an introverted thinker and I'll pre-read the deck and be thoughtful about my takeaways. At dinner, my colleague said, ‘You know, his [extroverted] way isn't always the best way.’” Karen learned in this conversation that while learning from others’ leadership is valuable, it’s also important to value your own strengths and lead from a place of authenticity. “That conversation was the impetus for a more intentional approach to what styles I want to emulate and which parts of my own individual style I want to embrace.”
At this turning point, Karen contemplated what style qualities she wanted to lead with. What rose to the top were four tenets: environments that encourage discussion, a desire for authenticity, an open door where all voices matter, and a friendly and collaborative team setting. She also believes in the importance of clarity about expectations, and if intentional about leadership, she can provide this cultural framework for her team.
Actively seek mentorship and feedback
Beyond her experiences at Intuit, Karen has worked for great managers who have mentored her, investing in her coaching and development. This wasn’t by accident, though; Karen intentionally chose roles with people she respected and from whom she could learn. These mentorships were successful when celebrating Karen’s wins while also not hiding the truth when things weren’t going as well. “They gave me tough love and at the same time supported me along the way.”
While giving and receiving feedback can be difficult, it’s necessary for growth. “People think that giving tough feedback isn't nice. I think it's the opposite. It’s not nice not to give feedback. If I don't know what I'm doing wrong, I can't improve.”
Being a female leader and a mother requires prioritizing
Karen’s dad was a printing salesman who grew up in a household that sometimes struggled to make ends meet. “For him, a measure of success was earning enough to provide for his family. He wanted us to have comfort, and also some small luxuries – not big luxuries – but small luxuries he didn't have growing up. To achieve that he worked long hours – sometimes 18 hours a day – and I remember as a kid holding onto his leg as he walked out the door dragging me behind him, and me saying, ‘Please don’t go!’”
Karen’s dad prioritized his professional success for his family’s financial security. Karen was determined to build on the security he'd given her, and do things differently. “I enjoy working and making an impact, but I want to be there for my kids as well.” To achieve that balance she is thoughtful in the choices she makes. “To be a mother and a business leader, you have to prioritize and you have to accept that you're not going to be there for everything.” A friend gave her a metaphor for working moms involving crystal balls and rubber balls. “You have to know which moments are crystal and if you drop them, you never get them back.” What’s required is determining which are the crystal moments and which are the rubber ones for you, because for each of us they’ll be different. “Is it going to a performance your child is in? Is it being there at night? Be really clear about what those moments are, realizing that some are rubber. If you drop them, they bounce.” Karen’s approach to those choices has involved staying clear on what matters most.
A lifetime of learning and curiosity positions you to drive a growing company to the next level
WEX has set ambitious - and achievable - long-term financial targets and Karen is helping - along with Kristy Kinney, Chief Transformation Officer - and others to lead this next phase of growth for the company. “WEX has declared who we want to be going forward, not just from a financial perspective, but also in our mission. Our mission is to simplify the business of doing business, which will benefit our customers and our employees. In delivering on this mission, we will also deliver great financial results. But, at its core, the next phase in the company’s development is about increasing our agility, creating a nimble company with an innovative mindset, and allowing reinvention as the world continues to evolve.”
With her team, with collaboration across the executive leadership team, Karen’s leading WEX in new and different ways. “We're investing more in our technology, operational excellence, data & AI, and innovation. We're also investing in more agile ways of working and increased innovation using small, empowered teams.” Clarity on roles and responsibilities is part of the formula allowing for faster employee decision-making. “The focus is also on more empowerment, more customer centricity, more experimentation, and on developing better data to help shape decisions. We're invested in building the foundation to provide employees with the ability to move faster with decisions across the organization. More innovation happens in this type of environment.”
To drive transformation and organizational change, clarity of purpose is essential, and a strong change management plan. “Does everyone know where we're going? I think we're getting increasingly clear about our priorities as a company. Are we winning the hearts of employees and customers along the way? Are we focused on telling success stories? Are we open to learning from failures? We're celebrating our successes, creating that comfort with failure, a learning mindset, and building confidence along the way.”
As an example, in partnership across functions, WEX teams are actively mapping end-to-end experiences, both customer and employee paths. Goals include understanding what happens each step of the way and seeing the journey through customers' eyes. “What we’re looking at from the customer perspective is how they discover our products, buy a product, onboard, and get support when needed.” They also look at the related employee experience - do employees have the data and tools they need? “Looking at that journey through the customer's eyes whether it be an internal or external customer, those three things – clarity of vision, change management, and the end-to-end customer experience – are crucial when driving transformation.” All of Karen’s experiences to date, mentors, coaching, an innate curiosity, and a focus on learning, empower her to lead WEX through transformation and growth.
Know your strengths and build a diverse team to complement them
There are myriad tools to help determine your strengths – Myers-Briggs is one of the oldest examples and newer ones include tests like Gallup’s Strengths Finder. When asked about how she feels about these kinds of tools, Karen pulls out her laminated strengths sheet she keeps by her side. “It’s important to be clear on your strengths, lean into them, and be aware of your opportunities.” The laminated sheet includes a diagram of her strengths and a diagram for leading people who are similar to you and people who are different from you. Karen’s strengths include being strategic, empathetic, and driving results. “I lean into those things. I embrace my empathic side and create cultures and environments that are embracing and open.”
She uses strength-finder tools to hire diverse teams. “It's fine if we overlap in some areas, but a high-performing team will include people with different strengths.” Creating an environment where different strengths and different voices can be heard comes next.
Karen prefers teams of individuals with strong traits, as opposed to those with more mild personalities, “I'd rather develop people who spike in some areas than those who hit the average for everything across the board.” She leverages her team’s strengths and helps them compensate or create support networks around them to enhance ‘opportunities.’ “If you are not as strong at project management, it's still important to be able to say, ‘Here's what's coming. Here's the status. Here are the risks.’ I need to know you’re going to deliver on time and if you're not going to do it yourself, totally fine, you just need to have a channel for that to be communicated. I lean into my strengths and build a team and coach people based on their strengths.”
WEX’s transformation and growth provide opportunities for the company and a great opportunity for Karen to execute on all she’s learned throughout her career. Karen has an innovative, open leadership style, and a customer-focused and change management skill set that position her perfectly to lead WEX through its next phase of growth and development. WEX is fortunate to have her helping drive that strategy.
If you’re interested in working for a growing and global organization that puts employees first and has a Chief Digital Officer like Karen Stroup, please visit WEX’s career page.