Much about Stephanie Nadi Olson’s beginnings feel serendipitous. Her parents met in a car accident in Atlanta at the corner of Briarcliff and Clairmont. The collision brought two vastly different worlds together. Stephanie’s father grew up in a refugee camp and emigrated to the United States from Palestine with less than an elementary school education. Her mother is white, a descendent of German immigrants. Both sides of the family are big, loud, boisterous, and to Stephanie’s eyes, nothing short of beautiful. The mixed races, different languages, and backgrounds are all an incredible gift—from a young age Stephanie came to know intimately the power of diversity.
While she grew up oceans away from refugee camps, her decidedly unwealthy childhood in the wealthy Atlanta suburb of Dunwoody introduced her early and often to inequities in the world. Stephanie grew up hearing stories of resistance and resilience that awoke a desire within her to never be without.
“I remember when I was young hearing these stories about my father’s family. My grandfather was a wealthy farmer and had his farm taken away from him at gunpoint,“ Stephanie recounted. “He was put in jail for going back and trying to fight for his land. There was a fire that was lit in me when I was really young just thinking about the injustice of that and how my dad luckily made it to the states. He was really kind of rebuilding our family name. He had so much dignity taken from him when he was in Palestine. From a very young age, I didn’t know exactly what I wanted to be, but I knew I wanted to go into business, and I knew that I wanted to make a long-lasting financial impact on my family.”
That fire drove Stephanie to begin working at age 14 for spending money. It took her from what is now Georgia State University’s Perimeter College to the Georgia Tech Scheller College of Business, where she majored in Business Management with a certificate in Marketing. While she went to school, she also worked several odd jobs close to campus— at a refrigeration company, as a server at Rocky Mountain Pizza, and as an account manager at an Atlanta smooth jazz radio station.
She didn’t realize it at the time, but she was laying the groundwork for the opportunity of a lifetime when she graduated from Scheller in 2006.
The Proving Ground at Microsoft
When Stephanie dropped her resume off at Microsoft’s table at a Georgia Tech job fair, she was certain they were really looking for engineers. She knew about Microsoft’s high standards; they never hired anyone into their advertising division without at least five years of experience. She didn’t know that Microsoft was specifically looking for undergrads young enough to intuitively understand the new landscape of social media advertising. Stephanie was hired a few months later as an account manager, becoming the first person in the country brought into Microsoft’s college hire program. It wasn’t easy. She felt she had something to prove every day going into work.
“It was overall such an incredible time to be dropped into one of the most admired and thoughtful companies in the world and to be able to help them reconsider some assumptions they had made about how work happened,” Stephanie said. “All of my colleagues were significantly older than me. I felt that tension for sure. ‘Who is this kid? Is she getting paid what I’m getting paid?’ I definitely felt the pressure to prove my value early on.”
Stephanie felt confident in the knowledge she’d gained about consumer behavior at Scheller. “I was dropped into this huge behemoth, global company that was saying, ‘We’re struggling with consumer behavior right now,’” she said. “I was able to consider everything that I had learned in school at Tech with my own lived experiences. It wasn’t long after I started that I gave the whole Atlanta Microsoft office a presentation on how Facebook works, because they didn’t know. At that time, it hadn’t been that long that you could even get on Facebook without a college email address. So, I felt emboldened to share my perspective, and I understood the context of why it was important to them because of what I had learned at school.”
Working at Microsoft put Stephanie in daily contact with some of the smartest people she’d ever met, and she thrived as she learned the fundamental building blocks of online advertising and how ad agencies functioned as intermediaries between marketers and big brands and the people selling ads. Learning what it took to be successful—How do you sell a product? How does it actually make money? Why do people buy it? What is the competitive landscape of online advertising look like? How are buying decisions made? —made up a rapid-fire course in business savvy and was like drinking from a fire hose. Stephanie loved every minute of it.
Sales and Acquisitions at AOL
Stephanie had come to know ad agencies at Microsoft and knew that she wanted a sales job. “I ended up leaving Microsoft because they wouldn’t promote me fast enough. I am super ambitious,” she laughed. “Type A. I was like, ‘How do I make more money?’ I quickly realized that the sales people were the ones ringing in the register. I wanted a sales job. It was really difficult to get into that position at Microsoft, so I left and took a sales job at AOL, which was a competitor.”
At AOL, Stephanie was again the youngest person on the team and felt the pressure to prove herself, a pressure she came to feed off of and use to advance her from someone who had never directly worked as a salesperson to an account director juggling newly acquired startups at a rapid pace.
“I joined AOL at this really cool time, because they were having this identity crisis. It was 2008. They were trying to shake the old dial-up, CDs, AOL image that they had to a forward thinking, modern group of web properties. At the time, Tim Armstrong had come over to lead AOL as the CEO, and he came from Google. He was certainly hired to bring that certain Googleliness and forward-thinking image to AOL, and he was doing that through acquiring startups.”
AOL acquired startups so fast and furious that Stephanie had a hard time keeping up with all the emails about acquisitions. But the whirlwind also brought an exciting energy to the company as Stephanie saw the old guard resisting change and the newly acquired employees feeling inspired by what AOL could become. Stephanie said, “These new employees were so excited about the company that they had built that got acquired by AOL. And I just found myself like a moth to the flame, so attracted to that startup energy. They had set out to build a company and to sell it, and they did it and the teams were so galvanized by their mission.”
At 26 years old, Stephanie became the youngest person to win the salesperson of the year award. At AOL, Stephanie learned that she could bet on herself. “I knew how to make money, because I was in a sales role. The other really impactful thing was my eyes were starting to open to this startup world. I just found that that energy resonated with me.”
Learning to be Present and Profitable
Stephanie knew what it was like to work 80 hours a week. She’d been doing it since she graduated from college. She was reaping the rewards and had found financial stability, and beyond that, success. In 2010, Stephanie got married and when she started thinking about starting a family, she knew the 80-hour work week was not sustainable. It was hard for her to leave AOL at the top of her game and go to a smaller company that not many had heard of, but she did it because she felt like she had to.
“I felt like I had to change the way that I was working to fit the kind of life I wanted to have outside of work,” she said. “That was a big moment for me. I had my first daughter in 2013 and my second daughter in 2015. At Tribal, I was able to make the money I wanted to make. I was able to work less hours. I was able to be successful continuing to build relationships with marketers. I was able to be present for my kids. That was a huge learning experience for me.”
In that process, Stephanie learned when it comes to women balancing families alongside their careers, you have to ask for what you want. “I think I’ve seen a lot of women who are suffering and struggling but are unwilling or nervous to say, ‘You know what, I can’t spend four days a week in New York any more. I want to have a baby and that’s not going to work for me. What can we do?’”
Stephanie left AOL because she felt like she couldn’t have that conversation with her employer. In retrospect, she wishes she would have been bold enough to ask for what she needed at that time. “No, you’re not always going to get the answer you want,” she conceded, “but man, I think a lot of times you might be surprised at what a good boss and a good company is willing to do to keep great talent.”
Company Culture Inspires a Better Way
Between the birth of her two daughters, Stephanie went to work at a venture-backed startup out of San Francisco called Flurry. She worked remotely from Atlanta and was there less than a year, but was struck by the palpable energy she felt on a team of less than 25 employees. They were smart people working together to solve a problem they cared about. That’s when amazing things happened.
Flurry was eventually sold to Yahoo, and Stephanie fell in love with the passion encompassed in the early-stage startup experience. During her time there, Stephanie took note of the company culture and the diversity of the team. Flurry was open and intentional about their mission and unafraid of growing from their mistakes. Stephanie said, “The company was transparent about challenges, and they included people in solving growth challenges. It wasn’t just isolated to a bunch of people behind a locked door; you really felt like you could influence the trajectory of the company even as a new employee or as a salesperson sitting in Atlanta.”
Making Her Own Magic at We Are Rosie
Stephanie began finding success working at some of the biggest companies in the world. Over time, she noticed a pattern. She worked for smaller and smaller and smaller companies. It’s all been part of the process of finding what really energizes and excites her.
Today, she is building something of her own that is dynamic and sure to change the way we work. In 2017, Stephanie founded We Are Rosie, a hiring platform that matches brilliant independent marketers looking for flexibility with companies like IBM, Meta, IHG, and Bumble. We Are Rosie is built on the premise that life happens, but unemployment doesn't have to. She works with a handpicked team, many of whom she first met in the halls of AOL as leaders of newly acquired startups. At We Are Rosie, Stephanie has felt the magic of locking arms with people she knows and trusts to build something incredible.
“It’s going to be hard,” she said. “It’s going to be messy. Hopefully, we’re going to have a ton of fun while we do it. We’re just going to stay committed to building something that’s bigger than what any of us could do on our own. I think that’s the magic that has to exist in any startup.” And that’s the magic Stephanie is intent on continuing to create at We Are Rosie as she pours all of her experience into a company meant to disrupt how work happens.
Stephanie has had numerous beginnings, each a rebirth of purpose and direction, so that her most recent project as founder of We Are Rosie feels like a culmination built on the backs of all the others. Stephanie’s resume is impressive, and in review, one can see how each job opportunity arose well-timed and well-suited for her current skills and her drive for continued growth. Stephanie all but collided with some of the biggest names in advertising and tech as they sought to change in innovative, meaningful ways. Yes, there’s a bit of serendipity at play. But mostly, Stephanie exercised a certain tenacity to get where she is today.