Mother of all role models
This conversation with Kristen Miller was originally published on October 16, 2018. Since that time, Kristen gave birth to her son, Malachi. As Kristen explains, “I had him on Thursday and was back in meetings on Monday, working from home. It was seamless without a maternity leave. Business as usual from Children’s Hospital.”
Malachi had heart surgery at two months old. The idiom, “sleep when your baby sleeps,” doesn’t apply to CEOs of babies and startups. In the first two months of Malachi’s life, Kristen and family were in and out of the hospital. He’s now nine months old and, “the happiest little guy. He’s truly a joy.”
Meanwhile, alongside her team at Stylyze, Kristen is focused on delivering against her original vision and product roadmap. Multiple top-tier retail partnerships have allowed the company to focus on execution instead of fundraising, and they’re hitting their milestones.
To enable the work, the team has gone to a remote organizational structure. “I can’t spare the time to commute,” says Kristen. “I’m so protective of my time blocks.”
Read more about Kristen below, and on GeekWire here and here.
Kristen Miller leads a tech company that uses machine learning to help major retailers offer personalized digital shopping experiences to their customers. Kristen has raised over $3.5 million in two rounds. Her customers are some of the biggest names in retail.
On December 23 of 2018, exactly one year to the date that she miscarried a baby in 2017, Kristen is due to give birth to a son with Down syndrome and a serious heart condition. He will require major surgery within the early days of his life.
As she moves into her third trimester of pregnancy, Kristen’s focus is on fundraising and preparing the Stylyze team for her maternity leave.
I wanted to capture Kristen’s story at this specific point because it’s uncommon to read stories of pregnant CEOs and how they’re managing that change on top of running a business.
The circumstances of Kristen’s pregnancy journey are not uncommon. Women miscarry. Women at the top work their asses off and delay having children.
What is stunning about Kristen is her willingness to share the tough parts that most of us would rather bury. Kristen has recast her heartbreak into fierce courage and a will to rally other women to live life fully as women and leaders.
In this conversation we talk about:
Being true to your needs as well as the business’ needs
Maternity leave as a forced growth mechanism for highly operational CEOs
Fundraising while pregnant
The importance of a supportive board of directors
This conversation was edited for length and clarity.
Underwire: What have you done to move through a growth period in the business, while also growing a baby, without depleting your energy?
Kristen: There’s a point to make in the set up to that answer. I’m a person who’s very attuned to my own internal balance and there are just things that I know that I need for myself to function regardless of if I’m pregnant or not pregnant.
For example, even in college I never once pulled an all-nighter because I knew that I would perform better if I actually took care of myself and got my sleep. So I’m very aware that there are a few things that I really need to stay healthy.
For me, sleep is number one. It’s huge. Diet’s huge. There are things that I know if I eat, it just tanks my energy and I’m in trouble and I get sick. Exercise is also important. Pregnancy changes the definition of what that means. Then, there’s time with my family and people that I love and enjoy to recharge me.
I think one of the things that has been a challenge through this season of pregnancy is that there have been a lot of really exciting opportunities and growth in the business, but also a huge number of demands on me.
It’s really hard to make time for life outside of the immediate stuff — my business is a baby and then I’m growing this baby. I also have a seven-year-old son at home and a husband and a family. So that aspect has been challenging.
But what I have made sure that I haven’t lost are those foundational things like sleep and diet and exercise that I know that I need.
In addition to that, one of the things that this pregnancy has given me is a shift in perspective. Sometimes I get so on the hamster wheel that I lose sight of what’s important and what I have to be grateful for.
So leading up to this pregnancy, we had a miscarriage right around Christmas last year (2017). It was a miscarriage where everything went wrong medically and otherwise. It was traumatic for me and it was traumatic for my whole family. For my son, who’s seven, he was so excited, that was devastating.
So that was a shift in perspective. Then three months later we found out we were pregnant again, which was actually a surprise because medically I wasn’t even sure that was going to be possible. And then fairly early in the pregnancy we learned that our son has Down syndrome and a very severe heart defect that will need open heart surgery. Hopefully he can make it three to four months after birth.
“Miscarriage…a baby with Down syndrome who will also need surgery…it’s that confluence of experiences, layered on top of everything else that has been a reset for me. There’s a different sense of what a good day or a bad day is. There’s a different sense of what’s important and there’s also a different sense of fearlessness.”
As the CEO, how do you prioritize what’s important when everything is on the line as an early stage company?
I struggle with that. I really do because the company is in a growth phase and I’m highly operational. My hand is in everything, which is super unhealthy, but it’s been necessary, just because we haven’t raised a huge amount of capital to where we can hire all the headcount that we need. So often I’m doing everything from the admin work, the bookkeeping, taking out the trash, raising the money, selling customers, onboarding new customers and managing the quality of the product and developing the product, it just goes on and on. That for me is the ongoing challenge.
When you layer on top of that this lens of, wow, I am going to have a baby. That’s another amazing thing. We lost our last baby on December 23rd of 2017. Lo and behold, that is the due date of this baby, exactly one year later to the date.
It feels like this miracle in and of itself. But come December not only are there all these responsibilities with work, but I’m having a baby. And not only am I having a baby, but I’m having a baby with serious health issues and this is very uncharted territory for my husband and my whole extended family.
“For the business, I look at it almost like the parent/child relationship. What do I need to do for this baby to position her so that there’s time and space to go through that other experience? What needs to happen? That is my priority as a CEO and really leaning into the fact that one of my number one jobs is raising capital.”
Frankly I’ve been pulled in so many different directions that fundraising just hasn’t been a focus, but it’s necessary. I don’t want to be in a situation where I have this baby and oh, two weeks later we’re out of money, and I’m dealing with that. That’s not the ideal, so prioritizing for fundraising, and helping empower my team by saying, “Look, I need to put my focus on these activities as opposed to these 30 things I was doing because we need to create some stability for ourselves for the long term. And so therefore, it’s going to shift everyone else’s workflow.” Having the discipline to have those conversations and then maintain those types of workflows, that’s been really helpful.
Letting go. And really staying out of it?
Yeah, which for me, has always been a challenge. I just jump back in too easily, so this has been a forced, in a good way, a forced growth experience with both of those things.
Then your focus leading up to the baby is fundraising?
It’s a couple of things. It’s fundraising and customer acquisition. We’re in the process of negotiating exciting contracts and just making sure that the revenue piece of the equation lines up as it needs to. And that the implementations that we have going live are successful so that the revenue follows. It’s really those foundational pieces around managing capital that come through investment, capital that comes through revenue, and managing expenses.
Given that you’re trying to balance two very different activities, fundraising and customer acquisition, how do you approach your time management?
Frankly, it’s not as scientific as it could be or should be, other than to say, I’ve prioritized certain client meetings for example. If it’s with either specific clients or certain members of those teams, like the C level or the VP level, then I’ll participate in those types of conversations. If they’re implementer conversations, then I won’t because my team can do that. Previously I might have been in all the conversations, now I’m a lot more strategic about which ones I’m participating in.
“Also, from an investment perspective, it used to be that I’d take any introduction, I’ll meet with anyone, I’ll talk to anyone. Now it’s a matter of being more focused and saying, well is this a genuinely a happy fit? Because if not I can’t network for the sake of networking right now. It has to be very purposeful and focused, with an outcome in mind. So I’m more careful with that process as well.”
What would you say to women who might doubt if they could run a venture-funded company and have a child?
Life is really short. As women, we push ourselves so hard and we sometimes make a lot of sacrifices, some that we should, but some that we shouldn’t. I put this off, a second child. I thought, “Oh I gotta wait till I’m done raising money or I gotta do this or I gotta that.”
It’s just taking the plunge, knowing that you don’t have it all worked out because you’re not going to have it all worked out. The reality is that things change and sometimes they change in ways that we can’t anticipate.
“We’re pregnant for nine months for a reason. It does give us some time to plan and adapt and I think if any of us are being really honest with ourselves, we might have an idea where we want our business to be in nine months, but none of us know for sure what’s going to happen and how things might be different than they are today.”
And so if having a child is something that is in your heart or is a priority, then I think you just go for it and know that it will be hard, but you’re going to work it out and the only way you’re going to work it out is by being in that situation, in that moment and being able to kind of reframe and reshape to what’s in front of you.
Is there anything else about maternity and running a business that you think needs to come to light?
There are a few things that, as women, we don’t talk about a lot. And I think one of them is just the subject of courage. I think that as women, we carry a lot with us and having the permission to share our stories and share our journeys with each other.
I recently connected with a female entrepreneur in Australia who had gone through a miscarriage. She was feeling so unsupported and didn’t know how to handle it or how to talk to her team about it. She also didn’t know what to tell investors and all these other things. So I think it’s important to open up a channel for a dialogue about some of these things that we face as women.
The second is, there is all kind of talk as we know in press and media about being a woman and raising money and what that means. Well, it’s an interesting journey to try to do that while you’re pregnant. Let me tell you, and I think there’s an elephant in the room and I’ll admit it, right, I’m starting to look like an elephant. But there’s this other elephant in the room when I walk into these boardrooms with investors [the abysmal percentage of venture funding for women-led companies]. I’m of the mindset that the only way we’re going change the numbers of women at the top is to go and kick ass.
“I’m encouraging myself and other women who find themselves in this situation, to not be afraid, to just go and do it. Who cares, I’m going be waddling into some boardroom nine months pregnant, trying to close capital. Is it ideal? No, but at the end of the day, it’s going to get done and then there’s a great story of encouragement to share with other people, that look, this is doable, you can do it. You can help change those statistics.”
Damn straight, if Kristen can do it in her third trimester with all the other stuff on her mind, get your non-pregnant ass in there, ladies!
One last thing that’s a positive add is that my board and our investor team have been extremely supportive of this situation. I probably have a unique situation. I’m very close to my board. They knew about all of it. They knew about the miscarriage and in fact, encouraged me after that experience, don’t give up on this. You should keep trying.
So the other side of this equation is that they’re really amazing people that are out there who will put their arms around us as women. They will support us through these decisions and through the hard things that we go through and so truly, my board has been so supportive and such a huge advocate of all of this. There are people out there who encourage us as women and entrepreneurs to bring our full selves to what we’re doing.