Q&A with Insight – Ajit Jain

Our Q&A with the Insight team continues this week with Ajit Jain, the Co-owner and Co-CEO of Insight Education! Celebrating our 18th Anniversary, Ajit looks back on his fondest memories. 

Where did you go to college?

I attended the University of Toronto in Toronto, Canada where I grew up. I studied Civil Engineering with a focus on structural engineering and construction management.

What is your favorite memory from your college days?

My engineering program was quite brutal so the happy memories are few and far between in all honesty. But I do remember an all-nighter in my second year for an environmental engineering class. We had to write code for the processes related to a water treatment facility and there was a bug we couldn’t find. Our group of four was going nuts trying to crack the problem and finally my friend, who is still my friend today, figured it out. We were filled with emotions that I had never before felt for schoolwork. It was likely a combination of relief, joy, and exhaustion all rolled into one and it drove us to dance around the computer lab like lunatics.

What inspired you to become a college admissions counselor?

My path to Insight wasn’t an obvious one. Purvi Mody and I met at the Stanford Graduate School of Business, pursuing our MBAs. Her lifelong focus had been education and I was looking for a change career-wise. After spending my summer at McKinsey & Co on two separate strategy consulting projects, influenced by the entrepreneurial spirit at the Stanford GSB, I was inspired to think of going out on my own after graduation. Although I interviewed and got offers from traditional corporations for full-time post-MBA work, nothing really got me excited. Serendipitously, while in Boston for an interview, an education company in Cupertino posted about selling their client list. Since I had no background whatsoever in education or college admissions, other than applying for undergrad and grad schools, Purvi Mody and I teamed up to make a bid for the client list and start Insight Education. Early on, I was motivated more by the entrepreneurial opportunity that Insight presented but as I slid into the counseling role I realized how valuable a role we play in the lives of each individual student and their families. And that continues to motivate me today.

What is the best thing about being a college admissions counselor?

There are two things that I enjoy most. The first is the moment, as a counselor, when you realize that an essay has finally made it to the finish line. There is no scientific method that tells us when an essay is final. Rather, it is a feeling you get that crescendos as you read the essay and ends with fireworks. The second is results season. As kids hear back from the colleges they’ve applied to and get their offers of admission, our office is filled with both nervous tension and pure joy. The way a student chooses to share the news and the words they use is just as exciting as the result itself! At this point in their lives, barely young adults, seeing and feeling that sense of accomplishment that they’re overcome with, with never gets old.

What is the most challenging thing about being a college admissions counselor?

One of our responsibilities as college counselors is serving as mediators between the student and his/her parents. This requires a skilled diplomacy and a great deal of patience. Especially when managing expectations in terms of a student’s preferred list of colleges to apply to and a parent’s preferred list.

Reflecting on the fact that Insight is now 18, what is your best memory from this time?

My fondest memory is hearing back from my first student to have been accepted to Stanford University. It was my first year working as a college admissions counselor at Insight and I was learning and doing as I went along. Seeing his email, which I believe said, “Yippee!” was a special Insight moment for me.

Looking forward to the next 18 years, where do you see Insight Education? What has changed, and what hasn’t changed? 

I hope that the company can continue to grow while honoring our mission and values. Many companies struggle to stay true to their identity as they grow and in our case, working with high school students, it is imperative that we don’t allow that to happen. 

Tell us about your favorite restaurant in the Bay Area

I have a nostalgic place in my heart for Celia’s Mexican Restaurant in Palo Alto because that was where I had my first meal after moving here. It was also where I celebrated my first Bay Area birthday and where my oldest son had his first birthday party!

Who is your favorite sports team?

Since I am obsessed with sports (along with my 7 year-old son), this is a challenging question! As a native Torontonian, I would have to say that I love the Maple Leafs, Blue Jays, and Raptors. The Leafs and Blue Jays were around when I was a kid so there is a lot tied to my childhood that those teams remind me of. I will never forget the Blue Jays winning two World Series, back-to-back, in 1992-1993. Celebrating on the streets of Toronto was amazing! The Raptors came along when I was in college so it was a huge deal in Toronto that Canada was finally part of the NBA. Locally I do love the San Francisco 49ers and they are by far my favorite NFL team.

What do you like to do in your spare time?

I wish I had a more exciting answer. But my spare time is spent with my family/two boys. I am especially busy with my older son as I zip him around from his guitar lessons to baseball and football practice. Life is busy but fun!

If you could pick any 3 people in the world to invite to a dinner party, who would they be and why?

I would invite Wayne Gretzky, Bill Clinton, and Bono from U2. Wayne Gretzky is my idol and in my opinion the greatest athlete of all time across all sports. I grew up watching him and idolizing him. I think that Bill Clinton and Bono are very similar individuals in spite of their very different paths. They can captivate a stadium filled with people or they can connect with a person one-on-one. Their charm, wit and concern for social issues is compelling and would make for an unforgettable dinner party.

If you had to pick a motto to live by, what would it be?

Don’t be afraid.

What is your favorite weather season and why?

As a Canadian living in California I always say that summer is every day. While it may get a bit chilly here and there in the Bay Area “winter” it doesn’t fluctuate enough for me to really sense a difference. Growing up I preferred Spring and early Fall because the weather was nice but less humid than a Toronto summer.

If you weren’t a college admissions counselor, what would your dream job be?

I would play centre ice for a professional hockey team and for the Canadian National Hockey team in the Olympics.

Where in the world would you love to travel?

I would appreciate the chance to drive across Canada one day with no calendar or schedule rushing me along. In spite of having grown up there, I know much more of the United States than I do Canada. Further out I’d love to visit Brazil, Argentina and possibly Kenya.

Any parting words of wisdom or advice to students?

You miss 100% of the shots you don’t take. Similarly, you will not attend 100% of the college you don’t apply to.