How We Are Rosie Founder Created a Business Built on Inclusivity and Meaning

Oftentimes, entrepreneurs are focused on looking ahead to the future. But what makes Stephanie Nadi Olson so successful is that she never forgets her roots. She attributes the start of her journey to her father’s bravery in coming to the U.S. as a refugee in the 1970s. After putting herself through college, she spent the next 12 years at companies big (Microsoft, AOL) and small, which she says provided her with a first look at how the world works and how different types of people are treated. Fast forward to today, Stephanie is the Founder and CEO of We Are Rosie, a flexible talent platform she started three years ago that pairs F500 brands and their agencies with independent marketing talent. Her mission: treat these marketers with dignity and connect them to major opportunities so that they can have the life they deserve. Discover what Stephanie’s “light bulb” moment was that led her to start We Are Rosie, how she fosters and maintains the relationships she’s built throughout the years and why she's on a journey to see what she’s made of. How did you get to where you are today? After the birth of my second daughter, I took a moment to pause and re-evaluate everything I had been chasing my whole life: a sense of belonging, worthiness, success, and got real with myself about my personal responsibility in creating a life that was meaningful to me. I didn’t want to waste all my privilege as a cog in someone else’s wheel after everything my parents and grandparents had endured for me to have all of this opportunity. After a decade of panels about inclusion, I wasn’t seeing the change fast enough. I determined I wanted to dedicate my life to supporting people who are marginalized by the rigid systems of work. After a decade of panels about inclusion in marketing, I wasn’t seeing the change fast enough and my light bulb moment was realizing that we needed a net to catch and support the brilliant marketers who didn’t feel welcome in our industry. How do you foster strong professional relationships as you grow in your career? It’s been informal for the most part and the relationships have ebbed and flowed along with my changing life. For example, the people I leaned on for guidance when I was early in my career were different than those who supported me when I was a new mother. Since I’ve started We Are Rosie, the female CMO community has come out in full force. These are women I’ve long admired and to see them reach back and pull me up is a truly humbling experience. I do my best to speak with them regularly, or at a minimum, send them periodic updates of how the business is doing and where we are headed. I want them to stay included in this journey that they have helped shape. What’s one way you’ve invested in yourself that’s had the most impact over the course of your career? Hands down, a leadership coach has completely changed my outlook around leadership, building a business, and how to let myself actually be supported instead of shouldering the burden by myself, which was a big one for me. I’ve had to completely shift my mindset around just about everything–both in business and about the change I want to create in this world. How do you view work-life integration, especially now, and what advice can you share with others who may be struggling with it? DISCLAIMER: I love working. The way people love training for a marathon, or knitting, or traveling, I love building a business with every fiber of me. It is the fullest expression of me at this moment in my life. So, it’s really a matter of integrating the 2 things I care the most about in this world: my family and my work. What has helped is listening to myself instead of everyone else out there telling me what my work and personal life should or shouldn’t look like. Can you recall a situation where you've dealt with typecasting in the workplace? And what advice do you have for other women on how to overcome typecasting at work? It’s been a rollercoaster of typecasting I’d categorize in two ways. The first is the typecasting that comes from ignorance with no malice intended. This is the “we’ve always done it this way” typecasting. In these instances, sadly, we have to educate people. I often start with “Have you ever considered doing this a different way?” to figure out if progress can be made. If not, you may actually find that you are in the second typecasting scenario where people are knowingly, willingly standing between you and opportunity or respect. In that instance, just get out of there as fast as you can. What’s one tip you can share or something you’ve learned on how to handle salary negotiations or raises? The best advice I can give here is actually to parrot the advice of Cindy Gallop, a dear friend, We Are Rosie board member and absolute bad ass. “Ask for the most money you possibly can while keeping a straight face.” Ask for the most money you possibly can while keeping a straight face. Running a business where I get to see the compensation requests of around 7,000 people, I can tell you without a doubt that is what men do. I’m fortunate in that I’ve had an inclination to do this my entire career. Who has helped you in your journey and how did they help shape your career? I have industry mentors who help me consistently as I navigate the “everything is new!” territory of scaling a startup. The common thread with all of these mentors is that they have helped me see what I am capable of. They have pushed me to think bigger, to elevate myself, and to keep going when it would be significantly easier to give up. What’s the single best piece of advice you’ve ever received? The pain is the portal. This first came into focus for me as I prepared for natural childbirth with my first daughter. My doula said “Steph, it’s going to be intense. You can’t fight it. It has to be intense. You are bringing new life into this world and during birth, you have to embrace that it’s going to get more intense before it gets easier. Don’t fight it. That’s how you get your baby here the fastest.” And my god, if that mindset hasn’t served me well in entrepreneurship. As difficult as life can be, it’s all part of the process. Don’t fight it. Don’t be surprised by it. Don’t dwell on it. What does success mean for you? From a business perspective, I want We Are Rosie to be the de-facto source of flexible marketing talent for the biggest companies in the world. I want to be the example other businesses point to when they want to prove that taking care of people and building an inclusive organization is good for business. I want to make progress that will continue to snowball so that my daughters will be able to work in a way that makes sense for their lives. It’s a bit more fuzzy on the personal side. I am looking to my past and the experiences of my ancestors to really paint the picture of who I am and what got me here. For now, success personally looks like continuing this journey and to continue to push myself to do things that make me screamingly uncomfortable in an effort to really know what I am made of. The ‘Unaccounted’ MENA Summit Featuring Stephanie Nadi Olson and More Inspiring Leaders