Curiosity as a Compass: Ilana Habib `11 on AI, Education, and Venture Capitalism

Ilana Habib ’11 has never been someone to follow a set path, and she says that mindset has shaped both her early career and where she is today. Long before artificial intelligence became a mainstream topic, Ilana was already working at the forefront of the field.

At Cincinnati Country Day School, Ilana discovered the freedom to shape her own direction. She pursued photography and worked with the school’s marketing and communications team, experiences that encouraged both creativity and autonomy. She credits Country Day with teaching her how to think, not what to think.

“I appreciate the independence I was given as a student, along with the opportunity to engage in real dialogue with faculty and staff,” says Ilana. “I encourage current students to do the same, to remain curious and open to unexpected paths.”

She says her teachers set her experience apart, emphasizing the lasting influence of her English teacher, Fred Carey ’80, who died tragically in a bicycle accident in 2014.

“His impact stayed with me long after high school. It’s so important to take the time to say thank you to people who make a difference, because you never know where life is going to take you.”

After graduating from the Massachusetts Institute of Technology (MIT) and Harvard’s Graduate School of Education, Ilana spent a couple of years in the classroom before joining Mainstay (formerly AdmitHub) as one of the company’s earliest employees. There, she helped build conversational AI systems from the ground up, well before the current wave of widespread adoption. Working di­rectly with student-facing tools, she played a key role in shaping how the technology responded to real questions through con­stant iteration, feedback, and refinement.

“I was never someone who was going to do well being put in a box. I’ve always been drawn to curiosity, creativity, and finding my own way. That’s what shaped how I learned, how I led, and eventually how I built solutions for students.”

Her experiences at Mainstay meaningfully shaped how she thinks about both technology and the people building it.

Today, that perspective guides her work in venture capital. After earning her MBA from the University of Chicago Booth School of Business, Ilana now serves as a principal at Cintrifuse Capital, a Cincinnati-based venture fund investing in early-stage companies. She is also an active angel investor and works closely with student entrepreneurs as a coach with the University of Chicago’s College New Venture Challenge.

The transition was a natural one.

“The best founders I back have an earned understanding of their market. That is the same thing I learned building AI in education, that the best products come from people who actually understand the problem.”

Reflecting on technology during her time at Country Day, Ilana notes that it was a very different environment. The iPhone was introduced while she was in high school, meaning students were not yet navigating the same level of constant connectivity and distraction that exists today.

“In some ways, it’s a benefit that we didn’t have the technology students have now, but at the same time, they have access to more tools and information than ever before. A balance is required: AI should always be a tool, not a replacement for intelligence. While it can improve efficiency and support ideas when used correctly, creativity, curiosity, critical thinking, and media literacy are still essential.”

Article written by Miranda Johnson, communications intern.