Welcome to Beyond the Build. A new series from Shopify, where we share stories behind the Shopify ecosystem, a platform where founders, developers and innovators come to build for more than 1.7 million merchants worldwide.
Today on the show we have Karen Baker, the founder and CEO of ShipperHQ.
ShipperHQ is a Shopify shipping app that helps you take control of your online shipping experiences at checkout. Baker is infamous for doing things differently, questioning the norms and processes and she instills this type of challenge or mindset within her team.
In this interview, Baker shares her leap into entrepreneurship, the drive to build, and how ShipperHQ grew up alongside Shopify to become a global shipping powerhouse.
Watch the interview below, or read on for the full transcript.
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Trading foreign exchange for entrepreneurship
Fatima: We're so grateful and excited to have you. Share with us a little bit about the origin story of ShipperHQ and you yourself as a founder.
Karen: Yeah, absolutely. Thanks. I try not to tell this anymore because I feel like everybody probably knows it by now. I have a computer science degree by background and so I'm on the nerdy side of tech. I used to work in foreign exchange up in London, in Canary Wharf. This was back in 2008 and my husband was looking after the children.
I was the main wage earner and so that's how we decided to cut it and they were one and three and I've got to say he was not enjoying the one and three years.
One day I said to him as you do in relationships, "We'll sort it. I'll go into work and just ask for a year off." Thinking that they would never give me a year off but that was just when the whole diversity thing was kicking in. They said, "Yeah. Take a year off."
So there I was with two children and a husband at home and he was selling on eBay and basically the children were great but I'm definitely a worker and I needed something to do. I said, "I'll launch an ecommerce site."
I built an ecommerce site and solved the shipping problems in England. A lot of people started reaching out to me because I put it on some forums and they basically said, "Well, can you solve my problem? Can you solve their problem?"
Everything went crazy from there and we're in 2021 now—I moved to America in 2013.
ShipperHQ launched in 2015 and Shopify was one of the platforms that we first went on with ShipperHQ. It's been a crazy ride and really interesting to watch you guys growing up at the same time that we've been grown up.
Fatima: Take me back to that first moment. You kind of skipped over it, but it must've been a really hard decision for you to be the primary breadwinner and deciding to take a year off with kids and also start experimenting with entrepreneurship all at the same time.
Karen: Yeah. I don't think I really knew what I was walking into. Honestly taking the year off wasn't too bad at the time. I had a good job and we could afford to do that. We were definitely living. It was like making stews and let's live cheaply kind of year, but we managed through it.
The big thing was I've always been interested in stuff and doing stuff. I love my children, but I'm a better parent when I'm working. I realized that in that time that I had off. The jump into leaving my job, because I went back after nine months, I actually rang up my manager and was like, "I've had enough. I need to come back to work. Please, can you ring me and make it look like you need me back?" And he was like, "Yeah, come back."
I went back. And my husband was like, "I've got to go back." They needed me kind of thing, but really I wanted to get back to work. I've always been a worker, but after that, everyone just kept contacting me. I had the children, the husband, the job and people contacted me.
One day I was on the tube and I was like, "Something's got to give. I can't do all of these things." I never wanted to start my own company. I never thought of myself as an entrepreneur. Even now, I don't think of myself as an entrepreneur. I just decided and got off the tube, rang my husband and said, "Hey, I'm packing my job in." He was like, "Oh my God."
And that's what I did. Within two days I had a three-month notice period, but I managed to scam around that a little bit. Within two days I was out and I needed to earn £100 a day, which is what I worked out that I needed. I had just put my kid in private school.
Everyone thought I was crazy but I believed in ecommerce, I loved working with customers. When you work in trade in systems, you're not really working with customers. I really enjoyed the interaction and how ecommerce was. I felt that I could make a difference as well.
When risk tolerance changes: Seeking greater security
Fatima: You and I chatted a little bit about this when we talked last week, but it's funny because I think people sometimes associate technology entrepreneurs with a certain demographic. You're coming into this industry as a second career and what has that experience been like?
Karen: It's pretty interesting. We were talking about it because you've signed yourself around the company in your 20s. I never would have imagined that. When I was in my early 20s, my mother died and I had to leave university, go back home, and I went to work. I just wanted security at that point in my life. I felt very alone. I'm working for somebody else and them paying me money was just to me, [it was] just the greatest thing ever.
For many years, I was extremely happy working for somebody else. The fact that they would send me on a plane, I was like, "This is amazing."
But I reached a point where with that security side, I’d also look at my children and my husband and I wanted to spend more time with the kids. [To] be there and not be up in London.
He used to say, "Can you come back later after I've put them to bed because you're disturbing their bedtime," because I was so chaotic. I'd come in and be, "Let's all wake up." Like the dad does.
I'd be like that and he was like, "No, you can't do that." I was like, "Well, what is this?" That was one of the real things that drove me to do things differently and, strangely, to seek greater risk.
I've tried to also seek greater security for my family because I know that that's all they've got is me. People would ask, "What is your drive and motivation?" when I used to talk to mentors.
I'd say, "Security." It's not climbing Everest. It's not to be the biggest company in the world. It's not fame or power or money. It's just security. That drives a lot of my decisions honestly.
Fatima: How do you think that's trickled into the business decisions too? Starting ShipperHQ were you like, "I want to make this a profitable business for me and my family." Or, "I want to scale this into a big venture." I know you recently raised some money as well.
Karen: No. We haven't raised any money. A lot of people think we raise money, but that was actually Shippo. A lot of people have been congratulating me for raising money, but there is another female CEO in the shipping space.
It does shape your decisions. When you're younger, you can take much more risk because you don't necessarily have the mortgage. Some people are staying at home with their parents, they don't have children to look after. The whole risk factor changes.
I like to have cash in the bank and I like to be able to sleep at night, and I don't necessarily need to drive a Ferrari but I want to be able to pay my mortgage. I can take a certain amount of risk, but at a certain point it stops.
It has driven how we've grown. It's also driven the decisions around taking on investment, because you have to decide in risk who you trust, what you trust, and whether or not you trust other people more than you trust yourself and your mission.
"I don't have imposter syndrome and I do trust myself."
For me fundamentally, I don't have imposter syndrome and I do trust myself. I know that sounds a little arrogant, but it's not arrogance. It's just, I analyze things on a maths level and go, "Can you do a better job than me? Can you bring something to the table?"
I add it all up. So far, I haven't been able to say that somebody else could come in and do that. I think it's more of a risk than a reward for me right now. But that may well change and we often talk to investors and the numbers change and things change.
Defining success and turning away business with 70,000 users
Fatima: So take me a little bit through the ShipperHQ journey itself. You mentioned earlier that it started out your husband having an online store and you were building something for his ecommerce business. So at what point did that transition into, we want to make this a product and we want to scale it out and distribute it to hundreds of thousands [of people].
Karen: Yeah. The first employees were hired in 2010. I packed in work in 2009 full time. Then we were doing it as one-off downloads. So as an open source platform. This was before we went on Shopify, but quite early on, I realized that SaaS was the way to go. I was watching the Shopify story and other SaaS businesses in the space and I was like, "We are missing a trick." Because we were selling these kinds of zip files effectively as one-off.
We had over 70,000 merchants using our software: 25,000-30,000 paying customers on that solution. It was like, "How do you build this SaaS solution and build it via investment?"
What I used to say to my accountants was, "How little do I need to learn in order for me to concentrate on what is now ShipperHQ?" They thought I was absolutely insane.
They were like, "Karen, you're literally turning away business."
I was like, "Yes. Because time is more important."
"I'm a developer and an engineer and an architect, and you roll up your sleeves."
I'm a developer and an engineer and an architect, and you roll up your sleeves. We rolled up our sleeves hard in 2013-2015, and even today we do. I don't code so much anymore, but I still dabble. It's like yoga. I can't quite give it up.
Fatima: I love it. You were saying at some point you were turning away customers. What was that inflection point where you started to really see that scale?
Karen: Well, sometimes you have to know when to say no and you have to look at your long-term vision. We threw away our old brand WebShopApps and we knew we needed to go multi-platform.
We were watching the numbers on Shopify and we were crunching the numbers on what our app could do. We were looking at the science of that and we knew that we needed to get over there. When we hit the market, it was interesting for us coming from a different community into Shopify and really learning how the Shopify ecosystem works and the needs of Shopify merchants, because it is different. Shopify does think differently, but there's a magic in that as well.
You say, "When is success?" Well, I don't know. We're still walking the walk. I don't know if there's a real inflection point.
There's a point where you go, "I can afford to buy a bottle of champagne now." Maybe that’s success. I don't know. I remember once actually being at a conference and not buying a bottle of champagne and we'd done some crazy stuff. And then I thought, "Why am I not buying that bottle of champagne? Now let's just buy and expense it." But I haven't got that mindset.
Fatima: That's fair. Success can look a whole lot of different ways. It's just figuring out what it means to you, which is the most important thing.
Karen: Success, for me, is about time and enjoying the journey. It's not about being in the news or being the best at something. I will say this, I want to be the best for my customers and that matters. So I want to be able to look my customers, my partners, and my staff in the face and have integrity. Success is about having good morals and I just want to be able to sleep at night. It comes back to that.
Failing forward and embracing a whole new leadership role
Fatima: In your journey with ShipperHQ, were there any hard “fail forward” learning moments that you'd want to share with listeners who are trying to learn from your experience?
Karen: Yeah. I think transitioning from being a developer into being a CEO is a hard journey that is a continual journey of discovery and realizing what you're good at and what you're not good at. And then being able to push away stuff that maybe you’re not so smart at. It's a big transition. I know there's probably a lot of people that are going to be listening that are developers that are also single owners or have a couple of people.
"Me giving up engineering was a big challenge because that is my happy place. But you can't steer a ship and be down rowing underneath."
I'll say that you've got to give away the things you're best at, which is kind of weird as well. Me giving up engineering was a big challenge because that is my happy place. But you can't steer a ship and be down rowing underneath. There's a certain point regarding staff where you have to accept that you can't always stand next to them all the time, because you've got to set out a strategy.
There's been times of failure, where I've not managed to do that. I've not known, "Should I code downstairs or should I go upstairs?"
I struggle with that even today but I'd say that to everyone.
Fatima: How do you scale yourself and give the space to your team to do what they do?
Karen: You've got to let go. You've got to enable your team, let go, and you've got to trust them. You've also got to keep your eye on the fact that we have a team now, we're like 55, 60 people and caring like crazy. I have to care about the whole company and everybody's mortgage. I think about that.
You can't always think about individuals as much as they would necessarily want, because you have to always consider the whole and there’s a lot of variables in that. I never realized that you'd need that amount of emotional intelligence. I don't think I entered this with any of that at all.
Fatima: How do you think you went about acquiring it? Is it just trial and error of learning or are there any intentional tips and tricks you want to share?
Karen: It's a lot of failures. A lot of it's about hiring the right people around me that can support me, like my fellow colleague Quentin [Montalto]—who's our COO—is just a really happy, vibrant person. I'm a little bit more on the miserable side. We bounce off of each other and he's much more of a people nurturer than me.
I'm much more of a person that drives people up mountains. You need that kind of balance. I have that with my CTO, [Genevieve Eddison] as well. She's very placid and whereas I'm a bit aggressive. That's been the biggest thing, finding these key people in the company that can balance you.
"Until you really understand who you are, it's hard to understand what you need."
Until you really understand who you are, it's hard to understand what you need. There's a lot of introspection and with that comes—I say I don't have imposter syndrome—but when you introspect stuff like that, it's very easy to beat yourself up. You have to be careful not to do that because you are what you are and you can't change it.
Fatima: I agree that you need to know yourself well enough to understand your strengths and weaknesses and what you need around you to amplify impact. Part of building the right team—that's better than you in all the ways that they should be—you have to also understand what you're naturally good at and where to double down and what weaknesses you have too. There's just so much consistent learning, growth mindset is so important.
Karen: And I think everyone is like children and a huge muscle yourself or your peers. Everybody grows at different stages and does different things at different stages of their life. And I don't think you could say, "Well, gosh. She should know. She's like mid 40s. Surely you got to understand who the hell you are."
No, I'm just the same as you. I make lots of mistakes all the time and really big ones. I don't think that 20-year-olds can have it sussed completely and 50- [or] 60-year-olds don't. Some of us don't. It doesn't matter your age, it depends what you're doing there's still leverage you're going to do it.
Thriving on change in the Shopify ecosystem
Fatima: Totally. And there's always more to learn. There's never an end point of learning. Which is good.
Karen: That's the nice thing about technology and the wonderful thing about Shopify. I'm a person that loves change and loves new tech. The Shopify ecosystem is fantastic for that. And sitting there on some of it like the gaming sign. I wish I had more time to help my kids with all that and talk to me about it. The fact Shopify is getting into these different areas and exploring, they're just willing to think differently and all that. That's a great place to be because you are going to keep on learning, but you need to want to do it.
"I'm a person that loves change and loves new tech. The Shopify ecosystem is fantastic for that."
Fatima: Shifting gears a little bit, tell me. What are you most excited about for the future, both in the shipping industry itself and for ShipperHQ specifically?
Karen: It's been interesting with COVID-19 and how that's accelerated commerce online. I really think that shift's here to stay. I really like the way it is now. Before people would get in a room and it was a little bit stuffy and we would think a lot about decisions. There was a lot of red tape. Now, it feels like everything's just going faster.
People were just like, "We've got to do this now." That’s the single biggest thing that's really great. Now you can get on conversations with people at all levels and have proper chats.
In terms of shipping itself, the experience in the checkout has never been more important. As consumers we need to know when that parcel is going to arrive, otherwise we're not going to purchase it. It's as simple as that.
"As consumers we need to know when that parcel is going to arrive, otherwise we're not going to purchase it. It's as simple as that."
At this point, the world needs to get out there to get this solved. Amazon is an interesting space to watch, particularly around the fulfillment side as well. A lot of this hinges around shipping and how that works and how quickly we can get it there, whether we need to get it there quickly, etc.
I'm really excited to see what Shopify does, especially around marketplaces and into the fulfillment space as we walk forwards—and then how ShipperHQ can enable that for our merchants in the best possible way.
Fatima: That's awesome. I totally agree. The key is we want every single independent brand to be able to have and deliver on that delivery experience that customers are expecting more and more. What’s the next frontier you’re most excited to conquer with ShipperHQ?
Karen: We're working a lot around headless technology. I think that that's going to be a big thing in where you want to shop. SDKs and components move into that kind of architecture. We've been doing a lot of work there, so I'm pretty excited. The actual data analysis and—I hate the word “machine learning” because I just think it's programming—but it's that whole data analysis and then how you react to it.
With merchants, we see so many stories that are the same. We have enough data now to be able to say to merchants, "This is what we think you want to do," rather than us asking them what they want to do or saying, "This is a system you can configure in."
We can actually predict what they want to do and put options in front of them. For me, that's probably the final frontier that I'll take with ShipperHQ, but I'm excited for that one.
Everyone needs to shop and everyone needs to ship
Fatima: What are the primary markets you serve? I know you yourself, you were in London, the UK and now you're in Austin, Texas. Was that move for the business?
Karen: It was very much driven by the family. We were doing half of the business in America and come 6 PM the UK team used to switch off and I was left holding the baby and literally all of them,including the work. We moved to the US back in 2013. We serve all over the world. We sell in 80 countries or something like that.
In the dominant markets we have, of course, the US, Canada, UK, etc. But Europe is pretty big for us. And we sell out into Asia as well. Everyone needs to shop and everyone needs to ship.
"Everyone needs to shop and everyone needs to ship."
It's pretty interesting when you get down to [different markets and their needs]. I've had instances in Africa where we had to do shipping and we’d literally put the parcels on top of a bus and move them from stop to stop.
Somebody came in and said, "Can you solve that?" Sometimes these challenges, you sit back and you go, "Oh my God, that's crazy." But then you see the cultural differences.
[Another example is,] you see in New York where people are going around on bikes and the challenges around that. There's so many different things going on in different countries and you think that some places will be less advanced and actually they're more advanced. Especially out in Asia, their ecommerce is crazy out there. It's a whole different world. It's interesting because you can take the lessons and apply them back here.
Climb the next mountain or enjoy the view?
Fatima: Karen, for folks that are listening that are potentially starting their own businesses, maybe building commerce apps on Shopify or building in the shipping space, what advice do you have?
Karen: It's a difficult one. You've really got to want to do it. Make sure that you really want it, because you need a lot of perseverance to jump into this space. You also need to trust yourself. If it's something that's burning away, that you need to do, then do it. Nobody else is going to change the course of your life. That's under your control. You need to take control of it. I sat for many years frustrated in a job and didn't take that jump. I would say, if you feel too many days frustrated and you think you have a road out, then take it.
"If it's something that's burning away, that you need to do, then do it. Nobody else is going to change the course of your life. That's under your control. You need to take control of it."
When you're in a business, keep your head down and stay away from the lights and shiny Just try and stay who you are as much as you can. Be humble and respect other people. Sometimes people let their egos get in the way of the business and that's never good for the business.
Lastly my advice is, find your happy place because it's very easy. I feel this pressure sometimes, especially with investment, it’s very easy to feel like you should be doing what everybody else is doing. This is your life and your journey and what makes you happy doesn't necessarily make the next person happy.
There's too much pressure nowadays to just keep climbing the next mountain. Sometimes the mountain's got a great view. Maybe you should stay there. We are figuring that out. I am a person that keeps looking to the next mountain, so I should preach this to myself. I will say I have a good reason to do that, because it's disruptive. Keep climbing. You have to find where's good because otherwise you're never happy. I see that with a lot of entrepreneurs where they're never truly happy.
"There's too much pressure nowadays to just keep climbing the next mountain. Sometimes the mountain's got a great view. Maybe you should stay there."
No boundaries: Building a life within ShipperHQ
Fatima: In Shopify lately, we've been talking a lot about infinite and finite games. You need to know what your infinite game is and the horizon that you're working towards that doesn't really have an end. But then you also need to know, what are the mountains you're climbing? What are the finite games you're trying to win? Because putting that into perspective helps you balance what you're actually working towards and the greater mission of your own life.
Karen: You've got to live your life within what you're doing. I've spent time where I've not done that. And I do regret it. There have been times when I've missed seeing my kids doing something for the first time, but I've learned from that. I still probably make mistakes. But, I think about it a lot. That's a really good description that you've got of it. That's exactly it.
Fatima: So Karen, what is the thing that gets you out of bed every day about ShipperHQ? What's that thing that you realized is a really strong guiding light for yourself?
Karen: There's no boundaries and that's the thing about Shopify as well. There's no leashes on me, and I can get up and we can go. I love that about the company and I hope the staff feel that as well.
I'm sure you feel that where you are working. It's the greatest feeling ever of getting up and caring about the customers. A lot of the customers are my friends and you build a personal connection with them—I feel a responsibility to them. If I'm not excited to jump up the mountain, then it's a responsibility to the customers that gets me moving in the morning as well.