Meet Chaula Gupta


As the Vice President of The Fund, Chaula Gupta helps drive the organization’s strategic programming and initiatives and directly oversees its external engagement, operations and talent management work. Under her leadership, The Fund scaled its programs from serving twenty principals to nearly 300 over five years and leveraged its investments to grow several educator-serving startup organizations. In this role, she also helped launch The Chicago Principal Partnership and co-chaired a citywide education funders group focused on principal quality.

Why is The Fund’s mission important?

I think the quality of an endeavor depends on the people who lead it. If we want better education, better schools, better careers and outcomes for all students, then making an investment in the educators, in particular the leaders of the schools, is non-negotiable. The Fund’s mission is to remind people that education, in the end, is about the people. It is not about finding a silver bullet or a magic key that’s going to make it work for every student. The only way they can do that is making sure they have principals and teachers who know their communities, solicit input from everyone they serve, make decisions grounded in what’s best for students and bring along everyone with them. 

How have you “redefined leadership” in your own life?

As I’ve grown older and gained more professional experience my leadership lens has changed from just “making it up as I go along” to recognizing when I need to first pause and learn from work that others have already done. It has also become more important for me to not attach an ego to anything I do, to step back and evaluate my own work and say “that’s not good enough any more.” Even ideas that made sense when they were first designed might need to be scrapped and redone. And that’s fine. 

Was there an educator in your life who inspired you?

My high school math teacher would come early to school to make sure that we were getting additional support. She had high expectations and told me she expected me to be ranked on the citywide top 100 merit list for the 10th grade examination. I told her that there were other students who were smart enough to do that. She didn’t take no for an answer and I was so scared of disappointing her that I just put my head down and studied. And yes, I did place on the merit list. Bonus fact – in 2014, my teacher was honored with the Indian President’s Award for Excellence in Teaching. 

What’s one thing about your role at The Fund that might surprise people?

People come in thinking that we are a traditional philanthropy or investment organization and then find out that we are neither. We like to roll up our sleeves and work alongside all the organizations that we support. You learn by actually doing the work and by investing alongside the partners that you are investing in. You learn from the people that you are trying to support. This is an environment that doesn’t let you get comfortable in your role, ever. Your role changes, the context changes, every year is different.