Making a Career Leap to Education Leadership: What Public Schools Gain from Innovative Leaders from Other Sectors

Currently, in our public school system, career advancement is almost entirely dependent on years on the job rather than track record and performance. This means school leadership positions are out of reach for professionals with a wealth of expertise who want to redirect their skills toward education. It’s a missed opportunity. Leaders from industries outside of education have invaluable experiences and perspectives that can significantly contribute to innovation and improvement in a field that needs new ideas. 

As someone whose own career went through several twists and turns before arriving at my current role as a public charter school educator and CEO, I am particularly aware of how expertise in other fields can contribute to reimagining public schooling. My years as an academic and college professor inform how I think about the rigor of our curriculum and the skills and knowledge our scholars need to thrive in higher education. What I learned as a New York City councilmember shapes how I lead and influence my staff members, as well as our approach to empowering Success Academy parents as advocates for their children and school choice.

With these lessons in mind, two years ago, Success Academy launched a new leadership accelerator program, the Robertson Leadership Fellows program, designed specifically to leverage the expertise of professionals beyond education. The Fellowship brings in early-to-mid-career leaders from non-education fields and puts them on an accelerated path to school leadership so that our kids and our enterprise can benefit from their insights.

Fellows in our inaugural class came from fields as wide-ranging as digital media, tech, retail, management consulting, and law. Ethan Kessinger, for example, spent several years as a product manager at a tech start-up. He had recently completed an MBA from NYU’s Stern School of Business and was weighing offers from several tech companies when he learned about the Robertson Leadership Fellowship. 

From his perspective, the opportunity to swiftly advance to a leadership position managing a staff of 40 or more while working on behalf of a vital, life-changing mission was immensely appealing. From our perspective, his experience working in a fast-moving, ever-changing start-up environment was an asset. Success Academy schools are fast-paced and highly innovative — we always look for better ways to do things. When we find them, we make changes immediately — the next day, or even the next class! 

Flexibility in problem-solving and the capacity to pivot in the moment to meet the needs of customers (our kids and families!) are vital qualities for successful school leadership at Success Academy. While Ethan — like all our Robertson Fellows — had to learn about the ins and outs of education, the Fellowship is arming him with that expertise. Married with the strengths he has brought from his prior career, Ethan is quickly growing into an outstanding school leader.

Another Fellow, Tempest Whyte, came to Success Academy after serving as an associate general counsel for a real estate firm. To succeed in a highly competitive legal career, she needed drive, determination, confidence, and ownership over her growth — all vital to school leadership. When she worked side by side with teachers in her first year of the fellowship, she learned that keeping purpose front and center is even more important in schooling, when challenges and setbacks can feel highly personal and emotional. This insight is the springboard for her leadership as an assistant principal this year, as she cultivates grit, drive, and a motivating sense of purpose in her team of teachers.

Similarly, Tamanna Hassan had held a number of management positions at a large retail chain when she decided to pursue her passion for education as a Robertson Leadership Fellow. In her retail management roles, she was responsible for ensuring her teams had the training, support, and motivation they needed to meet revenue goals. She brought the strategies, skills, and tactics she learned when she came to Success Academy. 

This expertise gave Tamanna a strong foundation from which to grow her leadership in the context of schooling, where the goal is not maximizing revenue but rather, kids’ potential. “I have come to understand that leadership is not just about rallying and empowering your team,” Tamanna reflects. “It’s also about discerning the full scope of opportunity in any given situation and thinking outside the box when developing approaches to obstacles that come up.” 

Our Robertson Leadership Fellows bring vital expertise to their schools and to Success Academy — but they also embrace their role as learners. No matter how much experience and knowledge one brings from different fields, education leadership is highly specialized and much can only be learned by doing (I still am learning 15 years into this endeavor!). What makes the leap worth it, the Fellows report, is the unique combination of fast professional growth and unmatched positive and palpable impact. It’s accelerated leadership for a larger purpose — and the purpose of expanding educational opportunity and equity resonates to the very core of our ideals as a country. 

We are so grateful to our Fellows, and are excited to welcome more leaders who are ready to redirect their knowledge and expertise toward this project of reimagining American public education!

Interested in learning more about Success Academy’s Robertson Leadership Fellows Program? Visit our website!