As part of our series called “5 Things I Wish Someone Told Me Before I Became a C-Suite Executive” I had the pleasure of interviewing Emily Whittaker is EVP & President of Vistaprint North America, the expert design & marketing partner to millions of small businesses around the world. For more than 20 years, Vistaprint has empowered small business owners to live their dreams.
Over the last 11 years, Emily has held various roles at Vistaprint and its parent company, Cimpress, including product delivery, technology and customer experience. She also led the team that architected Vistaprint’s transformation effort and current organizational model. Her experience has given her unique insights into our small business customers from nearly all angles. In her current role, Emily leads thousands of team members across product, manufacturing, customer care, marketing and operations all striving towards the same goal: to deliver jaw-dropping customer value.
Prior to Vistaprint, Emily had a career in consulting with Accenture and The Palladium Group.
Thank you so much for joining us in this interview series. Before we dive into our discussion, our readers would love to “get to know you” a bit better. Can you share with us the backstory about what brought you to your specific career path?
My career path was heavily influenced by my mom. Growing up, and especially as I got older, I saw how much she got from working and having a technical career, especially. So she inspired me to go to James Madison University, which had an IT concentration as part of its business school, and that was the best of both worlds for me because it helped develop a systems thinking mindset and a way to think about problem solving in a business sense. From college, I worked in consulting, which ultimately led me to Vistaprint. Interestingly enough, two weeks before I had even heard about the opportunity at Vistaprint, my husband, who was starting his own small business at the time, discovered the company on his own. Seeing how excited and the wave of confidence he felt when he got his first set of Vistaprint business cards really made me want to be a part of what they were doing.
Can you share the most interesting story that happened to you since you started your career?
As I reflect on this question, I think it’s remarkable that the steepest upward trajectory (in terms of rate of promotion) has happened after I have had kids. I believe what that speaks to is that as a working mother, you have a unique perspective on what really matters, and you also build the skills to efficiently get things done. Some days are crazy hard, that is certain, but if you take a long term view, having balance has given me perspective and effectiveness as a leader.
Can you please give us your favorite “Life Lesson Quote”? Do you have a story about how that was relevant in your life?
One thing that resonates with me is “We can do hard things.” There have been so many times I have been on the leading edge of change and had the teams or people around me resist change because they can’t imagine what could be or felt that the path to get there would be too hard. The key is to put systems and processes in place to ensure everyone understands the vision and the journey to get there. When you break the hard things down into achievable parts, we can do amazing things. So when faced with a challenge, I often find myself taking a breath and repeating Glennon Doyle when she says, “Yes, we can do hard things!”
Is there a particular book that made a significant impact on your leadership style? Can you share a story or an example of that?
Lead From the Outside by Stacy Abrams has had a dramatic impact on me lately. I am just in awe of her impact in the world. In Lead for the Outside, she outlines how when you have passion, you harness your strengths, and dare to want more, you can drive impact. Her activism has impacted the foundations of our democracy, which is incredible, but her lessons are generally applicable. Making impact is about knowing yourself and what you stand for and turning that into action without free of failure.
What do you think makes your company stand out? Can you share a story?
I know this is cliché, but I truly believe Vistaprint is so special because it helps small business owners achieve their dreams. We make it easy to get professional marketing and design services. I am constantly inspired by the types of businesses our customers are creating, the range of services or products they provide exceeds my imagination. They provide their expertise, we provide expertise in marketing. And we know great marketing materials give validity to small business, and small businesses impact not just the individual, but the whole community. When you travel somewhere for the first time, do you notice the Applebee’s or the Target? No, it’s the small businesses that make a place unique.
As an example, my nine year old recently decided to start a dog walking business. She started by helping out our neighbors, then she started having her friends help, and they got together and designed posters and business cards to distribute around the neighborhood. Seeing her have that validation and confidence that came with having formal marketing materials was empowering to her and super meaningful to me.
The road to success is hard and requires tremendous dedication. This question is obviously a big one, but what advice would you give to a young person who aspires to follow in your footsteps and emulate your success?
My first piece of advice would be to not get in your own way. I spent a lot of time being afraid early in career — afraid that I wouldn’t know something, or didn’t have the skills — and that was such wasted energy. Because what was the worst-case scenario if was wrong? One bad day or meeting isn’t going to ruin everything. If you have something to say, say it. Be informed, have an open mind, but have a specific point of view.
Secondly, have an open mind and be open to opportunities that might look different than what you originally thought. If someone had told me I would be president of NA, I would have been afraid I didn’t have the skills. Look for signals and be mindful of how to be on a learning path and have an open mind of how you define success.
Finally, you are only as good as your team. You cannot do it all. Investing the time and energy to know and build your team is how you will grow as a leader, not to mention maintaining top talent.
Often leaders are asked to share the best advice they received. But let’s reverse the question. Can you share a story about advice you’ve received that you now wish you never followed?
A team member once told me I was taking too long to process information and make decisions, and encouraged me to make more “snap” decisions. I was always told to tune into my “gut.” But after working with them for a while, I noticed that their “gut decisions” often created a lot of churn internally. While a decision was made quickly, we often had to pivot or turn when the decision proved short sided. What I realized is that the gut decisions we were making were only solving part of the problem and what was being deemed as indecisiveness on my side was me spending time to analyze the problem. And that once I was confident, we understood the problem, the decision came quickly.
So, to me it is very important to me that we have a well-defined, well understood problem, then decide.
You are a successful business leader. Which three character traits do you think were most instrumental to your success? Can you please share a story or example for each?
- I am a systems thinker, meaning that I think about how a system is a product of the interaction of its parts, not just the sum of its parts. For example, I recently partnered with our CEO on how to organize Vistaprint to maximize value delivery on behalf of our customers. We knew it would be critical to balance team autonomy with a high quality, consistent customer experience that is best curated centrally. We architected a system that unlocks both — teams that can deliver at speed yet are rooted by high standards for execution and consistent platforms.
- Empathy: I can’t tell you how many times empathy has turned a tricky situation into a productive one. One example — when I was a project manager, a new senior leader joined a status update and they were getting increasingly frustrated because we wouldn’t agree to commit to a certain KPI. At one point, they were about to walk out the door and I said, “It’s so clear that you have a lot of passion for the project, I’d love to show you where we are so you can understand why we can’t commit to that KPI.” By recognizing where they were coming from, and sharing where we were, we were able to continue the project in a meaningful way together.
- Authenticity: I genuinely care about what I am doing, my team, and our customers. I bring who I am to the table and I ask the same of the people I work with. I encourage my team to challenge and debate me and have systems in place to provide a safe space for feedback loops. As a result, I have a high degree of loyalty on my team.
Ok, thank you for that. Let’s now jump to the primary focus of our interview. Most of our readers — in fact, most people — think they have a pretty good idea of what a C-Suite executive does. But in just a few words can you explain what a C-Level executive does that is different from the responsibilities of other leaders?
A c-suite leader’s job is to imagine what can be. You have to imagine a state beyond what is currently there and look to what’s next. When you’re making a strategic move, there likely is no precedent for what comes next, so it’s on you to imagine and champion the future.
What are the “myths” that you would like to dispel about being a CEO or executive? Can you explain what you mean?
That they have all the answers and always know what to do. When pushed we can always give answers, of course, but we need to lean on our teams to develop and execute our vision of the future. For example, we can agree on the north star strategy but we need our teams to help us get there.
What are the most common leadership mistakes you have seen C-Suite leaders make when they start leading a new team? What can be done to avoid those errors?
Pretending you are the expert and not building relationships with your team so they feel comfortable correcting and challenging you. My worst fear is saying something absolutely wrong and no one feels empowered to correct me. You absolutely have to build trust and foster an environment of communication with your team, because you can be so much more with them than on your own.
In your experience, which aspect of running a company tends to be most underestimated? Can you explain or give an example?
This goes back to my earlier points about the importance of building a team, but people management requires a significant amount of time and energy. Things like building relationships, developing career pathways and mentorship. You are only as good as your talent and developing talent takes time that often gets brushed to the side when we are also all busy executing to achieve a financial or a business outcome.
Ok super. Here is the main question of our interview. What are your “5 Things I Wish Someone Told Me Before I Began Leading From the C-Suite”? Please share a story or an example for each.
- Don’t be afraid to fail — We launched a more complex offering and it was a miss in terms of what customers were looking for. However, in that “failure” we were able to test, react and learn so we were ultimately able to build a better product. Your whole purpose is to fall fast and learn quickly, so they aren’t catastrophic failures.
- Have an open mind — When I first heard about the role at Vistaprint, I wasn’t even looking to make a career move. A friend of mine passed along the opportunity after hearing about it from a recruiter and thought of me. I never would have imagined myself here but I am so glad that this was the path I took.
- It’s all about your team — You’ll never be able to do everything yourself, so developing your team is always worth the effort.
- It’s fun — Working at Vistaprint offers a high level of strategic thinking, great customer opportunity and supporting small businesses. My to-do list is always long, but I love forming a perspective on what is most important and love the work I do. If it’s not fun, you might need a change.
- Take time to get the perspective you need — I build time for creative thinking, give myself space and time to gain perspective. In this go-go world, you have to build in time to get perspective to build your own perspective.
In your opinion, what are a few ways that executives can help to create a fantastic work culture? Can you share a story or an example?
Create relationships based on trust, whether with other leaders or direct reports. I make a point to say what I do, do what I say, and ask for feedback. Reward asking for help and giving feedback as much, if not more, than the wins.
For example, when someone comes to me asking for help, that’s how I know they will be a successful member of the team because it means they are confident enough in their skills to know when they need a different perspective. To me, that is gold!
You are a person of great influence. If you could start a movement that would bring the most amount of good to the most amount of people, what would that be? You never know what your idea can trigger. :-)
Eradicate the fear of failure and move the needle on confidence, not just for small businesses. So many people assume failing is not the worst that could happen, again, this sounds cliché but to me the worst thing is not trying.
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