Maggie Olson’s journey is one of innovation and resilience. Raised with strong female role models, she discovered her knack for leadership early on. At T-Mobile, she led initiatives for over 26,000 employees and created the Chief of Staff model from scratch. While pregnant, she took the leap into entrepreneurship, launching Nova Chief of Staff to train and certify the next generation of leaders. In less than a year, she grew the program to over 600 students across 20 countries, working with students from the biggest companies across the globe. Through Nova Chief of Staff, Maggie continues to shape the future of business leadership, providing the tools and resources necessary for Chiefs of Staff to excel in their roles and drive company success.
Remove the barriers for “how it should be” and imagine “what it could be.” – Maggie Olson
Takeaway:
Through Nova Chief of Staff, Maggie is leveling the playing field for women in leadership, providing the tools and training needed to succeed in C-suite roles. She is redefining how businesses approach the Chief of Staff position, creating resources and opportunities to help leaders succeed in high-level strategic roles.
Can you start by introducing yourself and sharing your inspiring story?
I’m Maggie Olson, the CEO and Founder of Nova Chief of Staff, a first-of-its-kind company dedicated to Chief of Staff education, certification, and development. My career spans two decades across industries including retail, tech, and food & beverage. I’ve always thrived in stepping into new roles, transforming teams, and driving results from the ground up.
My journey began at Nordstrom in the Buying Offices, where I honed skills in customer experience and project management. After earning my MBA at the University of Washington, I was recruited into T-Mobile’s Executive Development Program. Here, I eventually became the first Chief of Staff to the President of the T-Mobile Business Group. I built their Chief of Staff model from scratch, hired 7 people on my Chief of Staff team, and implemented processes, tools, and systems that are still in place years later.
Recognizing the lack of structured training for Chiefs of Staff, I launched Nova Chief of Staff in 2023. Our certification program has already supported over 600 students across 20 countries, including professionals from Amazon, Microsoft, and Salesforce. My mission is to redefine the Chief of Staff role, empowering leaders to leverage this position for strategic growth.
Outside of work, I love spending time outdoors with my husband, our pets, and our two-year-old, Max.
What made you decide to go into business for yourself?
Throughout my MBA program, I was drawn to entrepreneurship. But without a company, idea, or product yet…it just wasn’t time. However, what I learned was critical: “start thinking like an entrepreneur: problems to solve, efficiencies to create, white space to identify”…and I did just that. After finishing my Chief of Staff role at T-Mobile, where I felt resources & networks were dry throughout the role – I realized that Chief of Staff training was it, the white space I was not only passionate about but well-suited to solve.
How did you market your business when it was brand new?
The most important thing I did when I launched my company was reach out to every single thought leader in the space or in adjacent spaces. I didn’t expect calls back or any partnerships at all, but you know what? Nearly every single person I met wanted to work together. I knew it was a testament to our product and leadership, but even cooler it was a testament to the space I was in: a collaborative, friendly, helpful community full of people like me that really want to empower folks who haven’t felt resourced before.
What is a typical day like for you?
I launched my company right around the same time that I had my son, Max. As a brand new mom and new entrepreneur… It hasn’t been easy. But I wouldn’t trade it for anything. One of the many reasons I was attracted to entrepreneurship was being in full control of my schedule. As a mom to a toddler, I can’t love that enough.
A day for me is always different, but usually I work from about 11-5, and trade off between meeting days and flow-state (non-meeting days). My hands are in everything with Nova, and I work on everything including marketing, partnerships, growth, personal branding, and more.
If you had one piece of advice for someone just starting out, what would it be?
My advice: just start! And it doesn’t have to look the same as everyone else. Some need a fully established website, product offer, and email list before they ever sell a product. And others work contractually before they even have an LLC. It doesn’t matter how you do it… just start.
How do you prioritize self-care and well-being while managing the demands of your business?
I create “meeting days” and “flow days”. I suggest M/W/F as flow state days, and T/TH as meeting days. Don’t let meetings run your life. As a corporate employee turned business owner, I now take 95% of my meetings on Tuesday and Thursday afternoons only. This allows deep flow and strategy time that makes my team more successful, too. Remove the barriers for “how it should be” and imagine “what it could be.”
Meetings exist because forums are necessary to drive alignment and build culture across teams. But what also must exist is a dedication to the oversight of how you and your employees are spending their time, and a bias for action to make changes quickly, as necessary. Meetings can spiral out of control for many reasons: a new product launch, new leader, re-org, and more. While keeping in mind that change at work is a constant, as a leader you must ensure employee time, and your own, is prioritized above all else. Also, with AI’s assistance, meetings are becoming more and more manageable, for those who’ve adopted AI meeting productivity bots like Ambient, Fathom, and Parrot. These tools take project management and follow-up off your plate and can truly make meetings much more productive.
Some of us grow up with strong female leadership role models telling us to raise our hand, negotiate, and pull up to the table. And others don’t grow up learning these things. My goal is to level the playing field and provide hands-on practice that builds confidence, showing women (and men) that they can absolutely succeed in high-level, strategic, c-suite leadership roles like Chief of Staff. – Maggie Olson
What advice would you give to a new business owner? Or to your younger self?
I would tell my younger self (and any other young woman out there who found themselves landing a dream job) that even in great jobs with amazing teams and supportive leaders, burnout will take the fun out of work. Leading to an emotionally and physically draining environment. The best way to prioritize a healthy relationship with work is through reflection and awareness. For some this may be a mediative, spiritual, or physical practice. During your moments of calm and reflection, ask yourself:
Am I fulfilled at work?
What do I enjoy most/least about my job?
Does anything keep me up at night?
How am I showing up for my team?
Do I need to slow down or speed up on certain projects?
What support do I need from my leader & family to help me be successful at work?
Reflection leads to awareness. And when we prioritize awareness, we can spot early signs of distress or burnout much quicker.
Burnout can show up in many ways, here are several: Overtired, Unhappy/grumpy with loved ones, Chaotic and disorganized, Quick and rushed projects, Sunday scaries (dreading Monday mornings), and The inability to function well outside of work. It’s hard to truly know what a job entails until you’re deep in it. As an outsider, I thought being a Buyer at Nordstrom was all glitz, glamour, and samples, but when I actually got into the role I learned it was much more excel, purchase orders, and process. From an emotional perspective, this can elicit grief, disappointment, and confusion, all which are warranted. If you realize that your dream role isn’t all it’s cracked up to be that’s OK! You’re not alone here, it happens all the time.
What social media platform is the best for business growth and why?
In my industry, consistently writing about the Chief of Staff role on LinkedIn has been a game-changer. This approach has sparked dozens of partnerships that began with simple LinkedIn connections. I’ve embraced reaching out with a friendly message, sharing my goals, and inviting potential collaborators to connect. These LinkedIn partnerships have resulted in newsletter collaborations, podcast appearances, features, and many other valuable opportunities for Nova.
All of these and more are part of our interview series spotlighting successful women in business.
Melissa Stewart is the founder of SheOwnsIt.com. She is a Purveyor of Possibility, Entrepreneur Advocate and Coffee Addict. She believes that behind every successful woman is her story. What’s your story?
