Career Profile: Stephanie Nadi Olson, We Are Rosie CEO

After years of building her career in the digital marketing space, Stephanie Nadi Olson became increasingly frustrated with the way the industry overcomplicated work — so, she decided to do something about it. In 2018, the mom-of-two decided to launch her own company, We Are Rosie, to bring expert marketing talent to the masses, and today, Stephanie’s business includes four full-time employees and a network of 1,800 independent contractors.

You are the Founder and CEO of the company, We Are Rosie — tell us about your business and how you got to this point in your career!

When I graduated from college in 2006, I was very fortunate to land directly into the digital marketing space. I got a job with Microsoft as they were reimagining the way work happens. I was actually the first person they hired directly out of college to work in their advertising and sales division — it was part of a larger program they were rolling out. I went from digital marketing at Microsoft to AOL, which was a competitor for Microsoft Advertising at the time and was very fortunate to be at AOL through a bunch of acquisitions and to see the company evolve. Then, I worked at a startup that was sold to Yahoo!. I have this interesting experience of working at some of the largest companies in the world and also working at startups that were growing at a rapid pace and being able to see the differences between both.

My entire career has been in the advertising industry. I’ve had the opportunity to work with big brands like Disney, Coke, Home Depot, and Bank of America, and I’ve also worked with their advertising agencies. I started We Are Rosie about a year-and-a-half ago because I had a baby and a toddler at home. One day, I realized the way that work is happening in this industry is no longer working for me. All of these wonderful people that I’ve been able to work with throughout my career who have also grown up in this industry were experiencing similar feelings too. Feelings like, “I don’t want to give a 70-hour workweek. I don’t want to travel all the time. I want to do the work, I love my career, and I love this industry, but I need to work in a different way.” It was frustrating to me that I didn’t feel there was an opportunity for these people to work in a way that would give them harmony in their lives or the career they wanted, so I decided to build it myself. That’s why I started We Are Rosie.

Was it difficult to start your own company with two little ones at home?

When I started the company, my little one, Margot Rosie, was a baby. It was really scary to kind of walk off of this cliff and start the business. I knew there would be times where I was pushed to my limits. I wanted the name of the company to be something that was personal to me because I need that constant reminder of what and who I am doing this for. I think through our mission and the vision of the company, we’re able to change the way that work happens for people in the marketing space, but ultimately, we’re creating more opportunity for the next generation, including my daughters. The name is really personal for me.

I think that, overall, I was just personally frustrated with people overcomplicating the way work happens. There have traditionally been a lot of excuses as to why we can’t have diverse teams, why we can’t have remote teams, why we can’t have job shares, why we can’t give people harmony in their lives, and why we can’t view people as whole humans when they come to work. The revelation for me was that “no one is going to save us” and that “no one’s going to fix this for us,” so we have to build it anew. I think it’s never been easier to work independently, start your own business, or be connected with opportunity.

How much has your company grown since you launched a year-and-a-half ago?

The company is made up of four core full-time employees. I was the only full-time employee for the first year, so it was really exciting to get to grow the team at the beginning of 2019 and to add three more full-time employees to help assure the mission forward. We support a team of 1,800 independent contractors who make up the Rosie community, so these are people that range from the former Chief Marketing Officers of Fortune 500 companies to people that will run your social media to copywriters to PR experts and everything in between. When we think about our team, we think about our core team of the four (soon to be five) of us as well as the 1,800 independent workers who are a really critical part of our company. Our goal is to build a community for them so that they can feel a sense of belonging while working in an independent way.

We’re very fortunate to have gained a lot of traction really quickly. There are six large advertising agency holding companies, and we work with agencies within five of them. We also work with brands directly ranging from two Fortune 10 companies, about 12 Fortune 500 companies, and mid-late stage startups in the rapid growth phase.

What’s in store for We Are Rosie over the next five to ten years?

My goal is for We Are Rosie to be the de facto talent place for marketing. Every time people need specific, highly-skilled talent to handle anything across the marketing spectrum, [we hope] that they’ll come to us because we have the talent to do these things and we can deliver it in a “just in time” fashion. There isn’t any waste or bloat from unnecessary overhead. It’s just a really efficient way to access the exact talent you need when you need it.

Can you walk us through your daily routine?

I wake up around 6am with a little person in bed with me. I sneak out quietly so that I can get some work done before the day starts. I find that when I have that quiet solitude in the morning from 6am to 7am, I get a lot done. I’ll get organized for the day and answer any emails that came through overnight. This way, I’m not stressed out when I’m spending time with my family in the morning before they go about their days.

The kids wake up around 7am, and we typically eat breakfast together as a family. I joke and say that my husband is a short-order cook providing pancakes, eggs, French Toast, and bacon for us as a family. We eat, and then I get ready for work very quickly. I’ve condensed my morning prep and routine to about 10 minutes.

I head into the office around 7:45am, and my husband gets the girls off to school. It’s usually a long workday. I try to leave the office between 5 and 6pm. The girls are so small that they go to bed at 7:30pm, so it’s really important for me to get some quality time with them before they go to bed. I’ll come home, and we do dinner and bedtime as a family. We’ll read and get them to bed, and then I’m back to work until 10pm. Then, I shut it off and get ready for the next day. We’ve got a lot to do to run the business, but I joke with my husband that if I have any moment of free time, I’d rather do work than go to the spa. This business feels like my soul purpose in life, so I’m always very excited to jump back in — it doesn’t feel like work to me.

My husband has a long career as an engineer working at companies like CNN and Turner. When I started We Are Rosie, he actually joined the gig economy. I didn’t anticipate both of us to be working in this space, but to me, it’s a testament of how normal this is becoming. Now, he works as an independent engineer working for Google.

How do you and your husband divide parenting roles?

My husband and I had a conversation when I was preparing to launch the company and we were in agreement. We didn’t have any false ideas or romantic notions of what it’s like to start a business. We both know I don’t like to do anything half-ass, so we knew that it was going to be pedal to the metal as soon as I started the company. We made a decision as a family that he would be the primary caregiver for our kids for the next two to three years as I built the business. Anything extra that comes up in our day-to-day, like swim lessons, we try to split up.

What do you and your husband use for childcare for your girls? How did you decide that setup was best for your family?

Ingrid is in kindergarten, and Margot Rosie is in preschool. They are now at the same school which is delightful for us because we’re dropping off and picking up at the same place. Drop-off to school is 8:30am, and my husband tackles that, as I’m already at work. We are incredibly thankful and privileged to have a full-time nanny that works with us during the week to manage the household and to collect the girls from school at 3pm and take care of them afterward. If something comes up on my husband’s end in the morning, the nanny may take them to school as well.

We have a full village of others that help. My husband and I are both from Atlanta, so we have both sets of parents nearby. Every other week, my mother-in-law comes and stays in the house for two nights to spend time with the girls. She’s actually a retired kindergarten teacher, so she’ll actually go to school with Ingrid and stay with the class all day as a teacher’s helper. She’ll help out with the girls for two days which frees up our nanny to focus on household management.

We spend time with my parents almost every weekend. I’ll take the girls to my parents’ house, and we’ll spend time together as a family. I try to set aside two hours on Saturday and Sunday to keep up with work and to do the strategic planning that may have not happened during the week. We’ll either have my parents, my brother, or my sister to help watch the girls during that time. My brother and sister both have kids, so it’s fun for our girls to see their cousins. We’ve also got amazing teens in the neighborhood that will help from time to time as well. We truly have a village to support our family to give our kids lots of love.

How do you maintain self-care while being dedicated to work?

We’re really lucky to live by a nature preserve that is two blocks from our house. A few days a week, I’ll take our rescue dog on a walk through the woods. I’ll let him run off the leash while I listen to a podcast and let my mind wander a bit. Spending time in nature helps me to find balance. I also work with a business coach who is absolutely incredible. She’s a former Chief Marketing Officer of a Fortune 500 company who left corporate America to follow her sole purpose of being a Reiki Master and a coach for female executives. I work with her for one hour once a week. We spend about 20 minutes in guided mediation during that time. I don’t know what I would do without those sessions. Those 20 minutes of guided meditation of quieting my mind are so helpful in allowing me to think about the business in a strategic way, to think about my life from a macro standpoint, and be centered.

I’ve tried to incorporate working out in my day-to-day, but I feel like I don’t have the space for it. It’s not a priority right now for me at the moment. If it’s a beautiful day in Atlanta, I try to walk outside while on calls during the workday to get some activity and fresh air.

How does maternity leave work with your career, and how was it different after both of your pregnancies?

When Ingrid was born, I had a really incredible male manager that I’ve actually worked for three different times in my carer. I was struggling after she was born. I had undiagnosed postpartum anxiety and depression. I couldn’t name it at the time, but I was able to explain to my boss that I needed more time off. He said, “Steph, take all of the time you need. Work from home as long as you want. Keep the baby at home with you.” I went back to working after eight weeks and then full-blown after three months, but I did have the flexibility of staying home. I was fortunate enough to have had an in-house nanny during that time to help, and I was able to nurse, not pump, during the day. I was able to be close to Ingrid. I had a lot of anxiety surrounding the idea of letting someone else care for her. Being able to be in the house and knowing that she was in good hands helped me to keep that anxiety under control. With Ingrid, I had a nine-month quasi-maternity leave. I’ll never forget being able to be honest with my manager and to feel supported. Honestly, I still hit all of my sales numbers for the year and was able to work in a way that made sense for my life. That’s something I’ll always be grateful for.

It took being pregnant with Margot to realize I had postpartum depression and anxiety when Ingrid was born. When I was pregnant with Margot, I had this crippling fear of becoming a new mother again. I remember saying to my husband that I wanted another child, but I didn’t want another baby. Ingrid’s first year was the worst year of my life, and I didn’t want to do it again. We got therapy and help for me. My husband and I worked with a licensed clinical social worker who specialized in postpartum care. We addressed all of the things that I had gone through when Ingrid was a baby, and we were really able to get the help that I needed finally. We were able to put a name to what we had gone through as a family when Ingrid was born. I was much better set up for a happy, successful new mother experience when Margot was born.

When Margot arrived, I had a pretty traditional three-month leave. I went back to working from home after eight weeks because I like working. Overall, I just had a very different experience the second time around. I didn’t have the postpartum challenges that I did when Ingrid was born.

Your girls both experienced tongue ties and lip ties — can you tell us more about that challenge and how it contributed to your postpartum depression?

When Ingrid was born, I was very committed to breastfeeding. I breastfed both for two years, which was part of the “mom guilt” thing. I was like, “OK, I might not be around as much as I’d like, but I’m going to breastfeed these kids.” At two weeks, Ingrid had her tongue tie and lip tie clipped at a pediatric ENT office. I was like, “Great, it’s fixed! It’s not going to be painful to nurse my baby anymore.” But her ties grew back. That was really part of the helplessness that I felt during my postpartum experience. The doctors told me it was fixed, so it should be fixed. I knew something was off, but I didn’t trust myself because I was a new mother. I was really confused and disappointed that my body was letting me down. I felt like I didn’t have any support.

I had natural birth for both of my daughters, and for me, nursing was more painful than natural childbirth — without a doubt. I think it’s something we need to be able to talk about more freely. There are a lot of children who have challenges because of undiagnosed lip and tongue ties. It took me a whole year to come out of the haze and to take Ingrid to a pediatric dentist in Raleigh, North Carolina for a second opinion. At that time, she had the ties revised. Margot was a planned home birth, and at this point, I had done enough research to take one look in her mouth and say, “OK, she’s got ties.” Twenty-four hours postpartum, we drove to Raleigh to see the pediatric dentist to get her tongue and lip ties clipped. I attribute the fact that we got Margot’s tongue and lip ties successfully revised much earlier to me feeling much more confident in feeding and being a mother the second time around. I learned a lot about advocating for my kids and for my body through that process. It’s a lesson that’s served me through all areas of life.

How has motherhood changed you personally and professionally?

I tell people all the time that I grew up in a loving household, and I always assumed that “I love my parents so much, and they love me the same.” When I gave birth, I realized that you don’t love your parents the same that they love you… your parents love you so much more than you could ever imagine. That was a revelation to me. All of the crazy things that my parents did when I was growing up were justified. I get where they were coming from because now, I have this little person I don’t even know in my hands, and I would step in front of a train for them! It changes your perspective. You realize there’s more to the world then just the little bubble you’ve existed in to date. It certainly changes your priorities.

For me, I think it also made me a much more empathetic person — I’m not super emotional, I don’t love talking about feelings, I’m fairly straightforward. Motherhood, for me in particular, brought out this really empathetic, thoughtful side of my personality that, frankly, didn’t really exist before. I’ll also say that when you become a mother, a switch goes off. You’re more efficient than you ever could have imagined. I remember people mentioning that to me before I had kids and I would think, “There’s no way I can be more efficient than I am right now. I’ve maximized every moment of my life.” Being a mother, there’s just something that allows you to clearly be able to cut through the bullsh-t. You know how to triage any given situation like no other. So, I can look at a day where it is impossible to get everything done and I immediately know where to focus my energy and what pieces of that day are worth my time and effort and are going to give me the most return whether it be time with my family, getting a work project done, or spending time with my husband. I can now think of things on a macro level and know exactly where to focus my energy because energy is our most precious resource as people, family members, community members, and employees.

What are the greatest rewards and challenges of being a working mom?

I think the most rewarding part is really the opportunity to give them everything they need to become whole human beings who will one day be off in the world doing things on their own. Our girls are so different from each other. Ingrid is really emotional and loves talking about feelings, and Margot is a little bruiser who is a little bit more impulsive. It’s really cool to be able to care for each of them and to give them the love and confidence that they need to be their own person and to watch them blossom.

I think that the most challenging part is that I’m exhausted — all of the time. There’s also a lot of guilt. There are times where I think I should be doing more for them. I should be around more, I should be spending more time at home. It’s an impossible mental battle to win. You just try your best every day, and you have no idea if you’re making the right decision at any given moment. I have kind of thrown out this notion of “work-life balance.” I personally just don’t think it’s possible. I’m coming to terms with that.

When it comes to being a mom, what are you most insecure about? What are you most confident about?

I think I’m pretty confident that we can figure it out. I’m fairly confident that most parents also don’t know what they’re doing and that we’re making it up as we go and doing the best we can. I’m OK with that. I’ve come to terms with that piece of it. We’re just going to do our best and that will set them up for success.

On the flip side, there are still times where I want my mom! Like in the middle of the night at 2am, if my kid throws up down my shirt and the other one wakes up — in that moment, I look around the room, and I’m like, “I am a grown woman with two children and I feel overwhelmed. I don’t feel prepared for this. I should have it down by now.” I think there are little moments like that where you just don’t know what to do. But you stay in motion, use your judgment, and figure it out.

Dry Shampoo
Rent the Runway subscription
Iced coffee
Sobriety — I stopped drinking because it was slowing me down the next day.

Stephanie Nadi Olson is The Everymom…

Favorite family tradition? We go to family camp in Vermont on Lake Champlain at the start of each summer. It’s stunningly beautiful and an amazing way to get time to unwind while also getting lots of family time.

Easy go-to family meal to prepare? Uhh, take out?

Your dream vacation? A summer spent in Iceland with the family!

Last home item you splurged on? We’re adding a mudroom and screened porch onto our house at the moment. Quite the splurge financially and emotionally. Living through construction is a challenge, to say the least, but we can’t wait to get our laundry room out of the basement of our 100-year-old home.

Guilty pleasure? Extra cheese!

Most embarrassing mom moment? I once had a client walk up to my car window to say hello to me while I was pumping milk for my baby in the parking lot outside their office.

Proudest career achievement? Quitting a job that wasn’t serving me well to start this business.

Favorite date night activity? Dinner and a movie on the couch at home.

Best mom advice you’ve been given? It’s OK to say no to birthday party invites.

This CEO and Mom-of-2 Threw Out the Notion of Work-Life Balance—Here’s Why