VistaPrint EVP Emily Whittaker on Leadership, Innovation and Why Small Business Owners are Happy!

0:00You are listening to and watching Builders, where I interview CEOs, authors, authors, authors, and leaders about building businesses and careers. and today I speak with Emily Whitaker. She is the Executive Vice President and CMO at Vistaprint. You already know them if you're a small business. They do marketing, design, printing services, and more to help you grow. We talk about Emily's new research on small business, what she's learned about fostering innovation culture internally at Vistaprint, and a very, very cool articulation of how she transformed into an executive role. Thanks for listening.

0:37Hi, Emily. How are you? Good to see you. I'm well, John. I'm doing really well. Happy Friday. We talked offline about busy weeks. I know you're just back from overseas. I'm excited to talk to you about maybe things you've learned over there. But for the audience members who might not be familiar with Vistaprint, could you describe the business and your role there? Absolutely. Vistaprint seeks to serve millions of small businesses as their marketing and design partner. We really want to make it possible for these small business owners to bring their brands to life and any number of products to help them do their marketing, print marketing in particular.

1:12But we're not limited to that. We can also help you do digital, whether that be website hosting through a partnership with Wix or create digital content, and as well as express your creativity in any way that you can see fit. We'd also love to be your print operator of choice. So as small businesses have product experiences that require packaging or anything along those lines, we really want to be there for you so that these small businesses can be there for their customers. So it's really any different way that we can support small businesses. And then you have a big role there. Maybe describe the audience what you do on a day-to-day basis.

1:52So I get the unique and distinct pleasure of leading North America, which comprises of our two largest markets, the U.S. and Canada, as well as taking care of central marketing. And so effectively, I'm the CMO and the leader of North America. And those are two very different roles, but both very, very exciting. In North America, I'm making sure that we're looking after, do we have the right assortment? Are they at the right price point? How are we connecting with our customers from a go-to-market perspective? Making sure that we deliver, that we produce the highest quality product and that we deliver it to you as per your expectations, if not exceeding those expectations.

2:30And that's really the all-encompassing North America role. And on the global marketing side, I take after the brand. Who is it? How is it that we're trying to position ourselves? How can we be most salient and resonant with our small business customers? What is our calm strategy? As well as how does that calm strategy come to life across all of our channels? What is the channel excellence? How can we lean into new and emerging channels and channel technologies in order to make sure that we're present and our customers are aware of what we can do for them? Part of your role being CMO and you've got to know your customer, your customer being a small business, small business being a massive part of the US economy.

3:09And we also know this year there's been a lot of uncertainty, macro uncertainty in the economy that might be impacting small business. I'm really interested in some of the research that you recently released. You released a study on small business happiness, probably in the spirit of trying to get to know your customers. What did it reveal? And maybe answering the headline, are small businesses happy or not right now? Absolutely. And you're exactly right. What started as a survey a bit ago was to understand what truly drives small business owners. What is unique about them? What drives? Are they happy?

3:44And really trying to get under the hood of what that entrepreneurial spirit, untapping into what that entrepreneurial spirit is. And when we saw the results and we compared with what was going on with the macro environment, we decided we had to run the study again because we said, wait, is what we see here true even in this moment? And so we worked with YouGov. we ran the study once and then we repulsed a similar audience and we found consistent results that in fact, despite these circumstances, small businesses are happier than not. And what we really look into is the fact, and the data was very, very compelling.

4:2381 % of those surveyed said that they are happy or somewhat, either very happy to somewhat happy. If we dig into what's behind that. The drivers are that what seems to be true is that small businesses are happier working for themselves than for someone else. And 53 % are much happier now that they're out on their own. And we think that's because the happiness is driven by the things that they can control. They're willing to trade off stability for their independent freedom. They're being able to align their personal goals with their passions and bring those passions to life. And that that is in essence what makes them happier, despite the challenging environment that's around us, all of us.

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5:46Check it out at business.com slash plus that's business.com slash P L U S. Maybe I'm being a little cheesy here, but it's almost like the pursuit of the American dream is inherently fulfilling. Whether you call it the American dream or something else, but we have the power, I can't think of a better word, to make our own way with our own businesses is very fulfilling, it sounds like. I think you're right, John. I mean, I think truly, you know, if you think about the American, your own pursuit of happiness and that I think what we're seeing here is that the ability to pursue their passions and find a path to success there is what is uniquely satisfying to them, despite the challenges or obstacles that they may face and that they perceive their fate being in their own hands, as you describe that, as being very rewarding, even though there may be challenges along that route.

6:41You know, I wonder if one of the challenges or, you know, uncertainties out there is about disruptive technology. And I think like in 2025, I'd be fired as a business podcast host if I didn't ask about AI. I don't know if you addressed this in your survey, but how do you feel like SMBs, small businesses are adapting to embracing or fearing AI and tools like that? John, you're absolutely right. I think in today's world, we'd be 100 % remiss if we didn't bring up the topic of AI. And we did ask about it. You're right. It's such an important topic. I think it's something that we're all addressing both from a personal front as well as professionally.

7:22And small business owners are no different. And I think what was really interesting is that where we are in this moment, small business owners are using this to increase their own personal productivity. Slightly more obvious tasks of how can I boost. We know small business owners are out doing a tremendous amount of things. They're likely their own marketers. They're likely their own operators, their own customer support team. And so how they can maximize their impact in any given hour is absolutely important to them. And we see that come through. But what is really interesting is that in the way that where AI is now, that small business owners do still prefer and favor human contact as it relates to how the strategy behind their customer communications, behind their marketing, behind their product strategies, they're leaning in on their human element.

8:14In particular, nearly half or 48 % of small business owners say that they prefer a human touch for strategy for their planning and that 43 % still lean on people for their actual campaign execution. And so we see that it hasn't gotten into how they're developing their product strategies or how they're communicating to their customers yet. But where they really are leaning into it is for their own personal productivity. Is there anything else from the survey that surprised you or maybe confirmed your understanding of what's going on? Are there any other highlights to share? I think so. I mean, I think what's also incredibly powerful about the small business owner mindset, at least that emerged through our data, is that their continued willingness to learn and how they're needing to understand that their environment around them may be changing and their willingness to dig deep and learn and expose themselves to new things.

9:1273 % say that continued learning is one of the things that they enjoy the most about being a small business owner. Interesting. The fact that they're out there wearing many hats or they may need to learn different disciplines in order to survive, they find that incredibly motivating. And I think that's a really interesting dovetail to even the AI question that says we are on the brink of something big. I think we can all feel it, that the world is going to change around us as powered by these tools and technology that are emerging rapidly. And small business owners are going to have to lean into that just like the rest of us.

9:46But what's really encouraging is that they value that continued learning dimension. They find that as a source of personal fulfillment, which is driving their overall happiness. I came into this interview thinking very much a North American mindset. I'm going to ask you about American small businesses. But given your global role, it makes me wonder, at the highest level, are there differences that you see between the needs, the wants, the desires of the American market versus other markets that you serve? What we've discovered is that there is something universal about that entrepreneurial mindset and those small business owners and that Vistaprint as a whole, despite the fact that we'll do research across many of our countries, more likely than not, the results are common than different.

10:34There might be slightly different use cases in terms of the industries or the applications of small businesses or the way that they specifically want to communicate to their customers. It could be that, as an example, lawn signs is a big marketing tool for many of our small businesses. They're prevalent all over the United States, as I'm sure anyone who drives around might see one. Europe just doesn't have lawns. It's the same application that wouldn't apply there. They just don't have the same use case. And so signage as a marketing tool may manifest across a different product suite. But the need to get your brand out there, the creative tooling that they need in order to bring that brand to life is universal.

11:17And also that entrepreneurial spirit of what we did not run this survey, to be clear, this is US data. But I have a strong hypothesis based on my 15 years at Vistaprint that there's a large degree of commonality in what motivates entrepreneurs. You bring up being at Vista for 15 years. I'm curious. I want to ask a little bit later how the company's changed, but how do you feel like SMBs are different now fundamentally than maybe when you started? How have they evolved? I mean, it could be, are they happier? Are they not happier? I mean, how are they engaging with Vista differently, or maybe how do they operate differently?

12:00Yeah. I mean, I think what is fascinating for us to observe is just the number of different places that small businesses can and reach their audiences and how they do. And the evolution from it used to be that the instantiation of your business was with one of our flagship products, the business card. Now it's likely with your social handle and it could be with your logo and your social identity. And that is that moment where your business is established and is potentially real. But there's that universal moment of when that idea turns to something much more real. And so that's the same. It's just where that moment or how that moment is coming to life is happening in a different way.

12:44And this is where Vistaprint has emerged what we're able to offer really around logo services. We even have naming services that help you, hey, how do you take your idea and turn it into something that is tangible and possible? We can start first in that digital sense. We can bring you to life with your digital moment in terms of the website. I think that's the new natural starting place for a business. Whereas historically, when I joined, it was that business card. You could create instant credibility and legitimacy as a business because you just created that business card and you had something you could hand to someone that says, this is my business here.

13:23It exists. Now it's a little bit more digital first and it's a little bit more brand, a little bit more design oriented in the beginning. I think that's been a true trend that we've seen very different. I'm smiling because I remember when Vistaprint was a new company and I'm pretty sure it was, my recollection anyway, is it was disruptive in the business card space. You could just go online, create your business card and it'd be sent to you. And I think I did it for a consulting thing I was incubating at some point. some point in the past. This print now, though, is a few decades old. We just had our 25th birthday.

14:03I'm sorry to interrupt you. Oh, no, that's awesome. But we did. We just celebrated. Congratulations on that. And I have previously worked at companies that were 15, 20 years old. I was at Amazon. My current company is 15 years old. And you may have started the company with an extremely innovative idea. And then you become really good at operating that idea and innovation can become challenging. I'm curious about you specifically, if you agree with that, but then also specifically with your team, what's the process for continuing to foster innovation at a company that really can't be called a startup anymore?

14:46That's true. That's true. I don't think we can at all. I have a really interesting corollary to answer here. One of our missions at Vistaprint is to, one thing that we talk about is to help small feel big. This was centered in a lot of our campaigns that how do you make a small business owner that might be a sole entrepreneur or have a team size of 10 or even have a team size of 50 show up and compete against these really big businesses. And so this concept of how do we make small feel big is something that we talk about in the way that we can bring your brand to life and look legitimate and credible even against a much more bigger scaled competitor.

15:26But the inverse of that is true as well. And so at Vistaprint, how do you make big feel small so that you can tap into that entrepreneurial spirit and not let that innovation stymie? And you're 100 % right. We got our start disrupting business cards, but we did not let that. We did not rest on our laurels. And we have extended our product catalog tremendously using the mass customization disruption, where we can, we're able to produce many small, you know, small things. That's what we did with business cards. And we've been able to replicate that with signage, with promotional gifts and apparel categories, with our, just expanding our range of, uh, range of marketing material and just, you know, keep going in terms of these product launches because we understand and that's driven by what do our customers need?

16:17What do they need to be successful? And how do we make sure that we can keep offering those things that as those businesses grow, we're there for them? How do we understand what? And so it's rooted in this customer obsession, our deep and rich understanding and empathy for what small business owners need to in order to survive and thrive? And then how do we make sure that we have our teams broken into smaller entrepreneurial spirit where we can really go into these new areas and not just stay in place? And so it's interesting. I think our mission is to understand small businesses and how they can show up in a big way and make a big impact that they need in the world.

17:02And in order for us to do that, we need to make sure that this big company actually feels really small. And so we have cross-functional teams that have the resources that they need in order to deliver against clear defined opportunities as measured by the needs of the customer. And then they're given and empowered to execute against what those solutions might look like in order to best serve those needs. It's really cool about almost operating as a small business to serve small businesses, even though you're a larger company. I wonder if there are any ways, any leadership hacks or process or methods that you would share, and you shared one about having smaller teams, to have people live and breathe innovation or entrepreneurial spirit, even though they're working for a bigger company.

17:56I mean, I don't know if it's a hack, but I'll tell you that I think one of the most important things that I observe across VistaPrint is something that we call our Vista behaviors. And these are core drivers of how we evaluate leadership, leadership potential, as well as just how we speak culturally about how we want to be as team members. And two of those behaviors, I think, enforce what you're asking about. One, I spoke about it, is customer obsession. It is on us all to understand our customers, to be rooted in data, to be rooted in intuition and empathy for who it is that we're serving. In any meeting, the customer is at the table.

18:36And that's a really important perspective for us to bring just and ground us into every conversation that we're having. What problems are we solving on behalf of that customer? We know our small business owners. I'm married to one. They have no time for things like marketing. as much as we can do to break it down and make it easy. Because when my husband is actually doing marketing is likely from 1130 to 1215 at night. That's just the reality. It's after he's done his day. It's after he's done, he's a builder, a contractor. It's after he's done his day. It's after he's gotten his invoices out and his new quotes, you know, in terms of advancing his business development, that's when he turns to marketing.

19:17I will tell you the energy level that he has to do anything complex or difficult is not high. And so again, just going back to those, and that's a common theme that we, across all small business industries, I know, we know time is tight. So how can we make it even easier for you to be successful? That is something, it's that customer obsession and making sure that's core to who we are and how we're talking about what our opportunities are and really what problems are we solving on behalf of our customers. That's just number one. The second is how do you act like an owner? And that is everyone feels accountable to what it is and how we're trying to do.

19:57No job is, it's not, it doesn't fall outside of your job description. Anyone can take it up and pick it up. And if you were the owner of Vistaprint, which if you were the owner, what would you do in this moment? And how do you think about the right constraints in the right way, whether that be on the expense, on the cost containment side, but also in terms of thinking about what the opportunity is and how we can shape that opportunity and how we can execute to move into that opportunity. We have others relentlessly learn and improve is another great one. But I think the hack that we have is that we reinforce those.

20:35It's regular for us to go back to those. I celebrate those at the end of a meeting. Hey, hey, I really saw a customer obsession on display here. It was really awesome when you did this. And make those a part of your culture of how you speak about one another, about how you recognize one another, about how you talk about the success. And to me, that's really important in terms of driving that entrepreneurial nature, because it means that there's no closed door. You can walk through any of these things. All of us are acting like owners. All of us are serving the best interest of our customers. And that to me is just, I think, one of the hacks that we can do.

21:13It's hard to achieve. It requires constant watering, tender love and care in terms of making it grow. But it is, to me, I think it's one of the most important things that's been a driver innovation of innovation across this print. I think that's such a great articulation of how to make company principles successful, because we all on the wall are in frames, the principles of the company. But when they're part of the review process, when leaders use those phrases over email, when they're subjects of company meetings, and then you have all those other things too, it really makes a difference and is essential if you're trying to scale.

21:56I mean, Amazon, I mentioned I was there before, They're so good at that, at a company that's growing like crazy in terms of employees. How do people get assimilated and march in the same direction when a leader can't talk to everybody every day? So hats off to you guys. I couldn't agree more. We are influenced. I think customer obsession comes and even the way that our behavior is articulated might actually be taken from with love from Amazon's. Inspired by. Inspired by. Why not take something that's really working? And that adoption has been paramount for us. It's been really important. So I'm curious, I want to ask you some questions about your career.

22:35So you've been at Vista Print a while. When you started, what was your role? And did you have your sights set at that time on an executive role? And then it was yes or no, but I'm also curious, kind of like what was either a big break or a big aha moment when you knew that you were ready to lead a huge part of the company? I came from a consulting background and I started at Vistaprint in, I'm aging myself, but in what was a project management discipline. So this is before the Silicon Valley definition of product development was introduced. And so, you know, software development lifecycle and the product management aspect around that was something that I was brought in to do.

23:15And it was in our manufacturing. What are the algorithms that control our proprietary manufacturing systems in terms of making sure that we're producing what we need to produce such that it meets customers' expectations, but in the most efficient way possible. So taking inputs in terms of labor availability or material availability, as well as shipping costs and other costs, and helping to make sure that we're making the best decisions in terms of what we're going to produce is what we need to do in order to maximize what we can do with our resources and still meet or exceed customers' expectations.

23:51So I was working on algorithms that ran their manufacturing system. I'm not sure I was thinking at the time of leading all of what was North America. So over time, I got increased exposure to, I went from working within the manufacturing facility, and I wasn't in the facility, but working on the systems that run our manufacturing facilities, to then thinking of the entire vertical integration, I was working on new product introductions. So how do we expand those product categories that we're able to offer? How do we bring those to life through merchandising? At the time, and this was 2012, 2015-ish, I don't know, we were solving how do we compete against the local print shop where customers can feel the substrates, can see the effect of a glossy paper or a polymer finish and see what that looks like as it refracts light.

24:48We needed to do that digitally. So we were solving problems of how do we bring this to life through great merchandising all the way to how do we actually create new production processes that scale? That was just an incredible opportunity to see the top of the house all the way down to how do we bring this to life to meet customers' expectations from a production perspective. And that just, I kept building and building from there. And soon I realized that I had not, there was not a part of the company that I hadn't been a part of through that experience. And at one point, our founder CEO, Robert, asked me to go on a walk.

25:29And he said, listen, we have a leadership opportunity on the executive team. I'd like you to consider it. It's to lead North America. and I was surprised. I was just like, really? And for a minute, there was a back of my mind, a small voice that says, do you think you can do this? And then I said, absolutely. There was this confidence that I'd really grown up inside of Vistaprint professionally. And I'd been curious about every part of the company. I'd supported things in marketing. I'd supported things in product. I'd supported manufacturing. I'd been in merchandising. There has just been, And through that curiosity and the opportunity to jump from various roles, I realized that I knew this company inside and out.

26:14And importantly, I really understood what our customers needed just because I've been exposed to the space for so long that I was, I'll admit, a little nervous stepping into some really big shoes, but confident that I was going to be able to walk in them and eventually run. And that's been the case, thankfully. That's an amazing story. That's great. And also just reinforces the importance of internal rotation at an organization and being diligent about understanding all parts of business. I know that like Microsoft, Amazon, many, many bigger companies, rotation is such an important part of having huge leadership roles because they feel like you understand a 360 scope of the company.

26:59You mentioned that little voice when you were going on a walk with your CEO founder. On the flip side, when you sort of look back, it could be at FistPrinter prior in your consulting career. Is there anything that you feel like has held you back that you would tell your former self or maybe someone that you mentor at FistPrinter outside the company to really focus on to achieve what you've achieved? I think you hit on it when I mentioned that small voice. That small voice was a big voice for a while. And it was active work to make that big voice saying, do you think you can do this? Do you really think you can do this?

27:36You don't have enough experience to do this. That was much louder earlier in my career than it is now. And because I've learned one fundamental lesson, you don't always know all the answers. How quickly you can learn and how quickly you can come to trust and bring in team members who can help you find those answers fast is actually the skill. not being the person who has all the answers. And it took me a while to learn that. I thought, you know, there's this be good versus get better mindset. And the be good relies on being that expert, is afraid to make the move until they actually understand and have all of the knowledge in order to truly be recognized as that expert.