As the Director of Talent Acquisition, Jesse Sherman plays a vital role in making recruitment season and Fellowship events effective, efficient, and, most importantly, unforgettable. He manages the entire early-career talent pipeline and applicant process, coordinates recruitment communications, travels to universities, and fosters excitement among current Fellows as they recruit the upcoming cohort of Fellows annually. All while project managing events that correspond with every stage of this process!
With a knack for connecting with people and fostering authentic relationships, he plays a key role in making recruitment season an exciting time for both candidates and Fellows alike. Now, let’s learn a little bit more about Jesse, from the man himself!
Take us on your career journey — what led you to this role?
I graduated from Indiana University with a degree in speech and hearing science, but at the time, I wasn’t sure what I wanted to do with my career. A connection with Bill Oesterle, one of the founders of Orr Fellowship, introduced me to two opportunities: Teach for America (TFA) and Orr Fellowship. After some thought, I decided to go the TFA route, which led me to an incredible 4.5-year journey in education at Victory College Prep.
During my time there, I wore many hats, including teaching 3rd-5th grade math, mentoring teachers, managing talent as the Director of Talent Management, and being part of a leadership cohort. Without a doubt, the most meaningful part of my time at VCP was the chance to teach alongside my wife during my last two years in the classroom. Sharing that experience with her was unforgettable and something we both cherish.
As my time in education came to a close, I started looking for my next step and naturally thought of Orr Fellowship. The role there seemed like a perfect fit, aligning with the skills and experiences I’d developed in education and through my non-profit work. It’s been an incredible journey, and I’m grateful for the opportunities I’ve had to make a meaningful impact while growing both personally and professionally.
What does your role entail? What are you most excited to work on?
In my role, I focus on connecting young professionals with meaningful opportunities that align with their passions and talents. There is no recruitment process like what we have here at Orr Fellowship and it has been so fun organizing it this past year. I’m particularly excited about mentoring new Fellows that I have been recruiting since August. I inherited two great classes with our current fellows, but it will be fun to see a class go through our program from start to finish.
What excites you about the future of Orr Fellowship and its impact on young talent across Indianapolis?
I think we have a lot of room to expand our impact. We got a nice test run of this with our Evansville chapter, and that went about as well as we could have imagined. There is a need for young talent across the state and country and I believe Orr fellowship has the secret sauce on how to access and develop that talent.
How do you spend your time away from work? What is one thing you wish people knew about you?
Faith and family are the most important parts of my life. Outside of work, I stay really involved in my church, Redeemer Bible Church, which has been a great place for community and spiritual growth. I also love spending time with my family, especially with my son. Being a dad has been such an awesome experience, and I’m soaking up all the little moments with my baby right now.
I’m also someone who likes to stay active. I love being outside, whether it’s working out, playing sports, or just hanging out in nature. Sports have always been a big part of my life—it’s something I really enjoy both playing and watching.
If there’s one thing I’d want people to know about me, it’s how much my faith influences everything I do. It’s the foundation of my values and the reason I approach life the way I do. My faith and my family are what keep me grounded and motivated every day.
In what ways do you get to engage with Fellows to support them during their professional and personal growth?
Orr Fellowship is special because it brings together so many different personalities and backgrounds. For me, my unique background and what might seem like random experiences have actually been my biggest strengths in connecting with and supporting Fellows. My resume might look a bit all over the place, but I’ve learned how to connect the dots and turn my journey into an asset.
Orr Fellows are so involved and motivated, which is amazing, but it can also make it tough to decide where to go next or how to tie your past experiences into your future goals. I love being a resource for people, helping them figure out how to market themselves and confidently navigate their careers. It’s incredibly rewarding to see Fellows embrace their unique paths and make them work to their advantage.
If you could describe your experience working for Orr Fellowship so far in just a couple words, what would you say?
Completely different from what I expected in all of the best ways.
What is a hobby or interest that you have that may surprise people?
I’ll give you a few with very little explanation: I love Nintendo, I am in an album club, and I enjoy playing all sports.
Final Question: What advice would you offer to young professionals who are just beginning their careers?
You don’t need to have it all figured out right now. We’re often taught to believe in the importance of a clear “career path,” and it can feel uncomfortable to step away from that idea. But the truth is, for most people, the career path they imagine at 22 ends up being very different from reality.
That doesn’t mean you shouldn’t have goals or jobs you’re aiming for in the future. It just means you should keep every door open and not say no to opportunities simply because they don’t fit into your 10-year plan. The best opportunities often come from places you didn’t expect, and being open to them can make all the difference.
