In Breakout Rooms, HubSpot Mentors Met New York Students Where They Are

On an August afternoon, a group of HubSpot employees logged into Zoom. Waiting for them were students from CUNY and across New York City: some in college, others still in high school, many the first in their families to pursue higher education. The mentorship event, hosted by The City Tutors and facilitated through Visit.org, split participants into breakout rooms where conversations unfolded in real time.

For Aiyana Karanja, a high school senior and City Tutors tutor, one exchange cut through the usual anxiety around grades and admissions. A mentor reminded the room that companies look beyond transcripts. “It made me realize we’re people, not numbers on paper,” she said afterward.

Another current surfaced: doubt. HubSpot mentors Eric Henriquez and Ky’Lend talked openly about imposter syndrome, noting that even established professionals face it—and that careers rarely follow straight lines. That reframing landed with students who’d arrived feeling “behind.”

The conversations also opened a window onto the tools shaping business behind the scenes. Several participants admitted they had never heard of HubSpot before the event. By the end of the afternoon, they understood the role of customer relationship management systems in how companies attract and keep customers—and why that knowledge matters for anyone entering today’s job market.

But the strongest moments were about community. Students congratulated one another on projects, shared LinkedIn profiles, and traded encouragement. One participant summed it up simply: “I came hoping to meet professionals. I left with connections, resources, and the confidence that it’s okay to have more than one passion.”

As the rooms closed and the chat quieted, Eric offered a reflection that captured the day’s arc:

“What stood out to me the most about the mentees is how vulnerable, hungry, and grateful the mentees were. The thoughtful questions they are wrestling with and their ambitious goals inspired me. I know what it feels like to be in their shoes; they just want an opportunity to make an impact and if they get it they won't take it for granted. I hope I was able to share even a nugget of wisdom but they definitely blessed me.”
— Eric Henriquez, HubSpot Mentor

For HubSpot, the event extended their expertise beyond clients and into the community. For City Tutors’ learners, it showed that mentorship isn’t a distant idea—it’s a conversation that can change how you see yourself and what’s possible. On an August afternoon, in breakout rooms with strangers who quickly became guides, students walked away with more than advice. They left with perspective, encouragement, and the sense that their future is something they can shape.