Sara Ittelson ’03 has found success in a multitude of professional realms. Currently, she is focused on early-stage consumer, enterprise, and AI companies, as well as co-hosting the podcast, Spotlight On.
[Editor’s note: this interview has been edited for length and clarity.]
Q: Since you were at Stevenson, you have done some interesting work in several professional realms and have been very successful at it. Recently, you launched Spotlight On, and this season has been highlighting AI. Tell us a little about the podcast, your work, and where you are finding delight in your professional path.
Sara Ittelson: I feel very fortunate that careers are long. It gives time and space to do a lot of things. I did a stint in consulting, then government, then grad school, and eventually moved to startups. Most recently, after a decade operating in startups, I’ve moved into early-stage venture capital. I had experienced the messiness of hypergrowth at places like Uber and Faire, and felt I could now add value to a founder’s journey. It’s exciting to spend my days meeting passionate founders and horribly difficult to choose when to write a large check and join the journey. That said, when you do fall in love in those moments and join the team, it’s incredibly rewarding to play a small role in their growth stories. The relationship with my CEOs and being someone who believes in them early is what gives me the greatest professional joy.
The podcast has been a really fun experience. From a business perspective, it’s been a way to project our viewpoint to future founders, and a platform to highlight companies we’re excited about. I am a podcast junkie myself and so may have daydreamed of another path as a podcast host and didn’t expect it to come through venture investing. Being a host on KSPB was a treasured Stevenson experience so I felt such nostalgia when we launched Spotlight On. I wish I had the data to compare “Sunny Side Up” with Spotlight On, I’m not sure which had a bigger reach :)
Q: Looking back on your Stevenson career, were there any experiences or moments that stand out as influential in preparing you for your chosen career path?
S.I.: Stevenson was an amazing environment to explore taking on leadership roles and different interests. I consider myself generally enthusiastic with lots of interests and passions. Stevenson was a place where that type of person could thrive. It gave me the confidence to pursue leadership roles while at college that later were truly foundational to the trajectory of my professional career, but the dominos started falling at Stevenson.
Q: You have probably learned quite a bit about AI, which is a very hot topic these days. How do you see it playing a role in learning and schools moving forward?
S.I.: I hope and believe it will elevate the things that are already critically important – deep understanding, creativity, and collaboration among real people to solve hard problems in the real world. It will allow for learning to be more individualized both in terms of filling gaps, but also using interests and passions as a vehicle for deeper learning. It will reduce crud and regurgitative ‘learning’ because that type of understanding will be even more commoditized by AI. It will make lifelong learning more practical and pervasive as enterprises adopt ai-enabled skills building not as a perk but as a critical means of staying competitively ahead. Changing rapidly so subject to change!
Q: As an alumna, you have always been very supportive, especially giving your time to serve on the Robert U. Ricklefs Alumni Committee, which helps choose the Ricklefs Scholar Award recipient each year. Do you have any favorite memories from being a part of that annual process? Any favorite moments with the candidates?
S.I.:Serving on the award committee has always been an energizing and humbling experience. The passion and enthusiasm of the students is contagious. You can’t help but walk away inspired by these young people who are wildly intelligent and ambitious. I enjoy reviewing the materials, but nothing compares to the interview process and hearing their stories directly. I leave with a deepened sense of gratitude and a bit of reflection that high school Sara would think I’ve done some cool things and so I should give myself a break on whatever I am judging myself harshly about that week.
Q: And, lastly, you shared with me something you did yesterday that you were nervous about, but very happy you did it. Will you please share a little about that recent experience?
S.I.: Oh boy! I did my first ever live TV segment and I was honestly quite terrified. The segment was on Bloomberg News and I was interviewed in their enormous NYC studio. I feared a public faceplant. It was a great reminder that if we aren’t doing scary things we’re doing something wrong and won’t have the thrill or reward on the other side. Every time I joined a startup or took on a new role it was scary and I, like most, suffer from classic imposter syndrome. But, then on the other side, you feel the satisfaction of achievement that only comes if you haven’t played it safe.
