How to Show up as the Leader Your Business Needs

0:00Hey, business besties. Welcome back to the Female Founder World Podcast. I'm Jasmine. I'm the host of the show and the person behind all things Female Founder World. Today, I'm chatting with Emily Whittaker. She's the Executive Vice President of North America and Global Marketing at Vistaprint. Welcome to the show, Emily. You are now entering Female Founder World with your host, Jasmine Garnsworthy. Hello. Thank you so much for having me. Can you give us a little bit of an introduction? What is it that you do at Vistaprint? What's your job? Absolutely. Yes. Well, I have the amazing opportunity to look after North America as a market, which is inclusive of both the United States and Canada, which are our two largest markets.

0:38And I also take after global marketing, which is our brand, our brand communications, our creative, as well as our channel, our channel strategy and our channel execution. So it's a really broad role. It's a really exciting role. But I basically get to understand the needs of our largest market, the US and Canada, and then build a brand and a communication strategy that ensures that our products are positioned so that we can meet those needs. That is a really big job. It's awesome. That's amazing. You've been at Vistaprint for how many years? Long time. 15 years. Just about. Yeah, it'll be 15 years in about two weeks time.

1:16Awesome. So we're going to talk about a few things in the show. We're going to talk about, you know, you're working really closely with small businesses and we're going to go through some of your advice, your learnings, things that can help small business owners as they're building their dreams and building their business. And we're also going to chat about your story and how you have up-leveled as a leader, built your team. All of these lessons that I think all of us who are building our own businesses, building our own teams can really learn from you. I want to kind of start in the evolution and the growth of your career and how you kind of moved into this leadership role and acquired the skills, the expertise to be able to manage and lead a big team.

1:56How many people are on your team now? Over 1 ,900. Whoa. That includes the amazing team members that make and produce and ship our products, and as well as our creative teams that make the amazing creative that is used and distributed across the world. Incredible. Okay. How did you move into this role? Let me know a little bit more about your career. Absolutely. I would say that I started my career in problem solving. I started with a big consulting firm coming right out of an undergraduate, and I was tasked with showing up at a client and having an answer to their problems. And that was a really daunting experience for me because I had very little real world experience coming out of just an undergraduate degree.

2:38But I was given the opportunity to learn as I went and apply these learnings to come up with an actual solution. And I realized I was okay at that. I was better than okay. I was actually pretty good. And I think what I was leaning in on was, I think I was born, my mom always said I was a born manager. And I've asked her again and again, what does that mean? And she says, Emily, you listen. And I think I had an uncanny ability to listen to what my clients were saying, to what the process owners of any various part of the process that we were looking to problem solve against were saying. And I could intuit where the gaps were, and then I could solve for those gaps.

3:20That became a pattern that I just applied again and again and again. And I went from consulting, which was a very travel intensive, road intensive, and I realized that the balance of my life between work and personal life was askew, weighted too much towards being the road warrior that I was. I was loving my job. I was loving the fact that I kept solving different problems. I loved the variability that that brought. I loved the diversity of use cases that I got to be exposed to. I loved the dynamicness of the teams and the diversity of the teams that I was working with, but I was ready to settle down.

3:56And so I looked for a company that had roots in my area, which was Boston, and I discovered Vistaprint. Strangely enough, I discovered Vistaprint two weeks after my husband, who is a small business owner, did. He discovered it through the customer route. He's a builder contractor. He was looking for business cards quickly fell into our, if you like business cards, you will also like algorithm. He got magnets, he got pens, he got key chains. And it was really amazing to see his business identity come to life. And he felt confident and real and established as a business. And it was really great to see what Vistaprint was able to do for him.

4:35And I said, that's funny. A recruiter just reached out. And so I was brought on into what was called the capabilities organization. And what we did was we solved problems internally. So it was very similar to what the consulting organization was doing, except my client was always Vistaprint. And I got to see the ins and outs of what Vistaprint was and how we operated. I worked to solve problems at our manufacturing centers. I worked to solve problems with the whole, how do we launch products and make sure our customers understand what these products can do and the merchandising needs of those products all the way down to, can we produce them in a way and can we get them to the customer in a way that meets our quality needs?

5:17And I've not left. That was about 15 years ago that I joined and it's been a journey ever since. Wow. What advice do you have for anyone who is listening to this conversation? They are in this position, you know, this is what I feel as well in my own business, where I'm in this position where the business has outgrown anything I've done in my career. And now I have to really like bridge this gap of showing up as a leader and a manager and these roles that I haven't fulfilled before. How did you develop those skills and really hone in? You said listening is something that comes really naturally to you, but what advice do you have for someone who needs to supercharge that leadership skill now?

5:56I think that there's, with any job that you're doing, I think that there's generally two dimensions to it. One, there's the functional expertise. And absolutely, that's an applied skill that you might've gone to school for, or you might have practiced in the function that you're actually an expert in. But then there's something more general, and that is leadership. And you can compensate by not having the functional expertise with leadership skills. And I will be completely honest with you. In my title, I told you I lead North America. I've had plenty of years of experience leading a P &L and driving the results within a regional capacity.

6:31But I have, within the last 18 months, just taken on the role of marketing. And if you look at my career history, I actually have, I dare say, no business leading marketing in that I don't have years of functional experience leading marketing. However, I have leadership skills. I go back to honing in and having the confidence that you can solve problems or that you can surround yourself by the experts who can solve problems and you can draw the best out of your team. and that is something that I've had to learn myself and I've learned that at various points in my career. It's okay to say that you don't know.

7:11It's okay to not be the functional expert. That can be leadership. It often is leadership. Knowing your limitations and being able to ask for help, to me, it's what I sell my team members. It's one of the greatest ways to build trust with me because that is in fact leadership and you can surround yourself with folks who have complementary skills. And that seems to be a great benefit to them because then that gives them an opportunity to rise to the occasion. And in the end, we all win from that. And so I'd say that there's a couple of dimensions. You can absolutely hone your skill and your craft, and that is extremely important.

7:52And that's a really fun journey to go on as you're growing in your career. But don't discount growing your ability to listen, growing your ability to communicate and alter your message, growing your ability to be able to bring people along and create a sense of passion and care for the journey that you're on. That's leadership, in my opinion. And that I think has been a large part of my success. And I think the biggest thing is that I can understand the mission that we're on. I can explain it to people in a way that fosters passion within themselves so that we are all on one journey together. And when you've got that behind you, you're absolutely going to reach obstacles, no doubt.

8:39But you've got to, between yourself and your team, you're well positioned to meet those obstacles. That's such great advice. I think for a lot of us who are in this position as small business zone is where we are, maybe you've created a product where you've solved a specific problem for yourself, but to bring it to scale, that requires hiring people who can do things that you have no idea how to do. And that's actually, you have to really set your ego aside to be able to do that and build trust with people to be able to do that, that you can empower them to let them do their thing. That's absolutely true.

9:09I realize this is a podcast about female founders and that is something I'm extremely passionate about. But what you just said resonates with me and my experience with my husband. He is a builder contractor. His passion is finished carpentry. And the output that he produces on any given day is outstanding. It's beautiful. However, he is not necessarily a marketer or a business development expert. So he has to lean in on sometimes, and it's exactly as you say, you know, a cut to his ego. He'll have to lean in to me. even that says, no, actually, let me help you. And as much as sometimes we don't want to have to ask for help, it's perceived internally by ourselves.

9:49We are our own harshest critics. It could be something that we think is a weakness. I think owning it is an absolute strength. I want to keep talking about this. I'm finding this conversation so interesting. And I want to kind of get into team building a little bit. We spoke about all of these people that you're leading, and I want to understand how you think about who to hire, how to hire, and how to keep people on your team. Yeah. Well, I think the first step is reflection. What is it that you're trying to achieve? What is the mission in front of you? We all don't have crystal balls, so we don't know exactly what those are, but give our best guess at what is it that we are trying to achieve.

10:27And then reflect on yourself. What are the strengths that I bring to the table? What do I, what do I, what can I do? And what are the, where will I be focusing my time and my efforts? And then ask the opposite question that says, and where will I not? And what can I not do? And that's where that look at honesty of yourself and your strengths and what your capabilities are and say, okay, well, given that gap, how do I fill that gap? And then you seek either the expertise or the skills around you to fill those gaps. But then that's that functional side. But I also think you need to look for the type of person that you're going to work really well with.

11:05And sometimes that's the direct opposite of the type of person that I am. I think it's really important to have diversity of thought and to have diversity of voices of who's around you at the table. I need someone who's going to share. And they can be an introvert but still be willing to share their perspective and have a position. because the worst case scenario I always tell my team is that you do exactly as I say, even though even one of you thinks that that's not the right way to go. I'd love to hear your position because let's arrive at what the next step is or what we're trying to achieve together.

11:38And so going back, I would compensate with whatever functional skill you need based on the mission that you're on. And then the second is what are the types of people that are going to draw out your best and what are those complementary skills? and then make sure that the dynamic that you foster with your team is one where people will share and speak up. And that can be in whatever form they want. Not, excuse me, not everyone is going to be the person who's going to assertively state their position, but maybe in a side conversation, they will share with you their thoughts and opinions because that's so important to make sure that you're challenged, you're tested, and that you're arriving at whatever the best outcome is for what it is that you're trying to achieve.

12:21Okay, business besties, I want to just pause for a second. I've got Natalie here on the Female Founder World team and I want to ask, Nat, are you ready for the holidays? Honestly, no. And I feel like it's coming up so quickly. It's coming up so quickly. And that's why I wanted to take a second to chat about this season's presenting sponsor, Vistaprint. It's honestly the best place to start holiday shopping. And right now, Vistaprint is giving all female founder board listeners an early holiday gift, up to 50 % off holiday cards, wall calendars, and more. Oh, wow. 50 % is a pretty good deal. How do you even have time though for all this holiday shopping?

13:01I know, honestly, like I'm usually pretty disorganized, but I've been quite on it this year. And we've also been sending out these really cute thank you packs to different founders who have been on the podcast, speakers who have been at the events. We've printed really cute like little fleece blankets. We have embroidered caps and also stuff for my family as well because you know everyone's going to be wearing the Female Founder World merch. Oh, of course. You got to bring the family into it. And I personally love a branded tote bag, but I also didn't know that they did embroidery. That's pretty cool.

13:31The embroidered caps are particularly cute. Oh, I love that. Highly recommend. So everyone go and get your holiday shopping buttoned up with up to 50 % off custom holiday cards, wall calendars and more at vistaprint.com. Use the code HOLIDAY50 at checkout. Okay, let's get back into the show. I can just picture everyone who's listening to this taking notes on their phone while you're talking. This is such good, helpful, tactical advice, which is exactly what we're all about on the show. So thanks for bringing that. I first started using Vistaprint when I was, I want to say, 19. And this is, you know, we've been partnering with Vistaprint in a really big way bringing merch and resources and programming to our community of small business owners.

14:13And when we first started the conversations, I was kind of, I had the story and I was like, I need to tell them the story at some point. I don't know if I've told you yet, but I was 19. I always wanted to be a business owner. This is, you know, the only path for me and one of those people. And I was still at university, but I started getting a few PR clients. I was studying marketing and PR and I went to Vistaprint. I printed my business cards. I printed a magnet for my car. I printed, I think I printed like a cap and a bag and it was like Jasmine Gansady publicity or something like that in the beginning.

14:47And I got real clients. I was 19 years old. I got real clients. I got them real press. And now to come full circle with this partnership, I'm just like, this is so incredible because genuinely Vistaprint has been part of my story since the very beginning. And I'm really excited to see how other small businesses are going to work with Vistaprint to bring their own visions to life in a really tangible way. And I know that you have small business stories that you want to share as well. So I'd love to learn a little bit more about how different brands are using the platform. I'm literally beaming at your story.

15:24I need to find photos of my car. Oh my gosh, I would love to see. And I'm impressed. You've been a customer for four years longer than I have. So thank you very much. That's incredible. And so I know you're asking about small business stories, but it's just, it's funny because I just shared my husband had the exact same, the exact same journey that you did with Vistaprint and it, and it has played a role in his, in any business that he's had since. And it's just, I completely relate to that. And that's just incredible to see. And I'll tell you, hearing your story and observing his, what I'm hearing come through, and this is what I so often hear when I talk to VistaPrint customers who have gone through journeys like yours, is this emergence of confidence that there's something about the instantiation of your business, of your idea that is now printed in real life on a physical, tactical thing in the world that says, this is me and this is what I can do.

16:23And the boost that that delivers is just, it gives me goosebumps every time I hear it. So thank you for sharing. Also, you know, if you're someone who's like lacking a little motivation at the moment, we're coming to the end of the year, things have been, you know, it's been a big year. Go and get yourself a branded cap. Genuinely. Nothing gives you a dose of inspiration, like slapping it on your forehead and being like, I am doing this. This is my business. Just the impact, just the impact that it can have just if three other people or two, you know, whoever else might see that. Yes, You're right.

16:53The message gets out there. Just in my town, there are these two sisters who I love so much. They're serial entrepreneurs. And it's so fun because I can walk down and I always accuse them. They have completely capitalized the allowance market in my suburb outside of Boston. And it is an ice cream store and a store for tweens. So between, you know, I'd say the customer base is between the ages of 10 and 14 years old. And hearing these two sisters' stories is just awesome. One started as a food truck. She had a passion for baking cookies and then learned that when you turn them into ice cream cookie sandwiches, everyone goes nuts.

17:39Yeah, give me some of those. Exactly. And so she started her business as a food truck and now she's actually got brick and mortar stores. and she inspired and her journey inspired her sister and more importantly, her sister's daughter who was 13 to start a business because she couldn't find a selection of products that she was looking for that was appropriate to her age. And what I love about this story is that it's obviously entrepreneurship was a family characteristic that seems to exist within this family. But the fact that they were solving for problems that were their passions, she loved baking cookies.

18:20It was an outlet for her of stress. And she turned that into a business that has then flourished and brought joy to all of her customers, including my two children, I should say. And then that story of that inspired her niece and her sister to start another business to solve a need in that community. And so Frozen Hoagies in Winchester and this Jewels, which is a shop where you can find things. They're Vistaprint. You can find stickers. You can find cups. You can find drinkware. But you can find things that appeal to that tween audience. It's just so incredible. And through our partnerships that we've had with other, say, the Celtics, the inspiration that small business does for me is just incredible.

19:07working with Rock City Pizza, who does Detroit style pizza in Boston. And the impact that he's made, he's used Vistaprint, and he's now gone from one store to multiple stores across Boston. It's just incredible. But then to hear some of the smaller stories where people, this is what to me is so exciting about entrepreneurship. There is no end to the level of creativity of what people and what people start their businesses to do. And the ways that we have helped are ways that I could never have imagined. And it could be something as simple as repurposing a business card to become a jewelry backing because someone is passionate about a particular type of jewel and they've turned it into something and then started at a farmer's market and then have gone from there.

19:58It's just there's no end to the creativity that entrepreneurs use and more importantly to me, the problems that they're solving and how relevant they are to their communities. Something that I've seen different brands in the community talk about using the platform for is to create their PR and influencer boxes, which I think is so clever. Creating these branded boxes, adding their own merch in there, making something that stands out, particularly if you're someone who maybe is launching with a couple of products, being able to add more of that experience in there, I think is such a clever way of using it.

20:29Absolutely. I mean, we've seen that again and again. And the type of the type of contents that folks are putting in and the way the credibility that having that box be branded, have your marks on it, look and feel like you and be filled with messages that are completely authentic to you is really powerful. And that's what's so amazing about what Vistaprint does is we're not just a stocked, you know, inventory. anything that comes through our platform is custom it's a unit of one and we love the minimum order quantities I'm so we need a low minimum order quantity to get started so I really appreciate that as well you're listening to you talk like your passion for small business owners it's just it's really coming across like I can really feel it and that's something that I think you know you've developed throughout your career do you have any advice for small business owners who are, they're on this journey.

21:25You're someone who is speaking with different business owners all the time. You're very much embedded in this space. What advice do you have for those of us out there who are on this journey? Yeah, well, I mean, I'm inspired by small business owners every day. And I mean, so I think I go back to that general leadership advice that I was giving earlier. One is know your strengths and please lean in. I go back to the creativity of what small businesses are solving for and the relevancy to their communities, please, if you have an idea, it's likely that others around you also need that. Yes. But it's important to know your market and to know who is it that you're trying to serve, who are your potential customers, and know where they are and how you can best reach them.

22:11And I think it's really interesting too that small, in the case of my husband or in the case of, you may be an exception given that you're probably an expert marketer, but so many of the small business owners that I interact with on a daily basis know their craft and they know their skills so well. They know their passion for what the product is that they're delivering. It's okay to ask for help when it comes to marketing. Not everyone. It's amazing. We did some research recently and over 70 % of the small business owners are also marketers. And that's a really tough job to take on. You described it in the beginning.

22:44A small business owner is not only likely delivering the product themselves and all that that entails, which I know is exhausting and a lot in and of itself. But then to be the person who's out there being the voice of the business, doing the branding for the business, making sure that the word of mouth is spreading in an appropriate way, driving those sales, that's a lot to take on. And marketing is really difficult. I know because it's a changing landscape. A company the size of Vistaprint always is needing to be evolving in our marketing strategies and tactics. And so I think it's really important to be able to ask for help and build a community around you because it is what I've noticed is that there's a lot of commonality in the types of struggles that small businesses have.

23:28And just by saying, hey, how did you solve this? You get so much inspiration. 100%. You need to ask other business owners. And I think there's something that comes as well from, I think, the vulnerability of sharing what you're having problems with that other people seem to want to like step in and help and also share what they're having their issues with. And it just normalizes, I think, and makes you feel a little bit more confident in yourself. A hundred percent. And I always learn something in that. And I agree with you. I think it's really the sense of pride that people feel to share when they've actually learned something is really great.

24:00And then, yes, just that relief of I'm not the only one who's going through that. I'm not alone here. Yeah. Emily, the last thing I want to ask you is for resource recommendations. If you have anything, it could be something that's been helping you as you've been leveling up in your career and as a leader, or something that you want to recommend to small business owners that they should check out on their founder journey. The thing that I reread every year, it's a book recommendation. We love a book recommendation. I'll put the link in the show notes. You probably already have it, but it's Atomic Habits by James Clear.

24:31Such a good one. I, this, the, the quote that stands out to me just consistently is you don't rise to the level of your goals, but you fall to the quality of your systems. And I think the daily habit is such an important tool that is often overlooked that the ability to make incremental progress just by building the right habits and that a little bit every day adds up in such an incredible way. And so just bring that level of intentionality. It's something, it's a reflection that I do every year. Hey, is what am I doing the right thing to do in order to help me achieve my goals? Because I can't just state the goal.

25:12I need to build the system that's going to help me get to that goal. And I don't know if that's helpful for folks, but for me, it's an activity that, it's a book that really resonated with me. And that particular mental note is something that I stick with and practice discipline or intentionality with what am I doing and what are my habits? Because those are the things that are going to help me get to where I'm really trying to go. I have a coach that I work with and I was saying to her, I don't have a nighttime routine. I don't have a morning routine. I just feel like it's just like such a mess and I need this to anchor my day.

25:45And she was like, you have a routine. Like you definitely have habits that you're doing in the evening. You just don't like them. Like write down what it is that you do every night because you're doing the same thing. Like you have habits. Right. You just don't like them. You just have to actually intentionally change them. Yes. And it's something that simple, but it's something it's often hard to do. Yeah. But once you do it and once you bring that level of focus to it, it really can make a difference. I love that. What a perfect note to end on. Emily, thank you so much for coming on Female Founder World.