When Seth Kessler WG99 brought the idea of Mind the Gap to his Class of 1999 WhatsApp group, there was an excitement in the air, even over text. Richard Yu WG99 remembers responding right away: “Yeah, I’m in!” For many of the classmates, the innovative program offered a chance to give back to Wharton in a unique way, by passing along their wisdom to the next generation. Mind the Gap launched in February as a partnership between the Undergraduate Division and Kessler’s company, GapWell, which Kessler founded with his undergrad classmate from Brandeis University, Lee Sosin. The Mind the Gap program helps Wharton students develop and strengthen critical networking skills by putting them into a real-world networking scenario with a Wharton alumnus. After several conversations about GapWell’s mission, the School’s Undergraduate Division and Kessler connected. The result was a custom program to help students practice the networking skills they learned, preparing them to launch into internships and eventually full-time careers.
“We’re not giving students a participation trophy,” says Kessler. “We’re giving them candid, real feedback, and pushing them a little bit outside their comfort zone.”
Using their expertise in student success, Kessler and Sosin wove Mind the Gap’s curriculum into Wharton’s popular Career Readiness program (known as CR@W) for first-year undergraduate students. Every spring, first-years apply to join one of two CR@W cohorts, which include sessions such as “Explore,” in which they learn about different career paths, and “Engage,” which builds practical skills such as email etiquette and cover-letter creation. Mind the Gap is the cherry on top of it all, offering students an opportunity to learn directly from alumni in the industries in which they hope to work.
Mindful mentorship: from left, GapWell co-founder Lee Sosin, Wharton Undergraduate Division’s senior director of strategy and operations Mike Elias, UD vice dean Cait Lamberton, UD director of industry exploration, alumni and corporate partnerships Ariel Robbins, and Kessler
Kessler already had a network of mentors at the ready. “Seth is a great connector,” says Liz Groo WG99, a strategic advisor and investor for All Court Advisory, a consulting firm. She describes Mind the Gap as a kind of “reverse mentoring,” with students jumping right in to establish deep and professional connections with alumni. The program kicked off with a “lookbook” that listed Groo’s name and industry alongside those of other WG99 alumni who agreed to take part in mock interviews with the first-years.
After reviewing the lookbook, Sophia Markowitz W29 knew exactly who she wanted to be paired with for Mind the Gap. Students request their choices of alumni through an online portal on a first-come-first-served basis. One minute after the portal opened, Markowitz had the interview partner she wanted. “Now I have someone in my corner I wouldn’t have otherwise,” says Markowitz. “And I don’t think I would have found her if it hadn’t been for this program.”
At the end of the interviews, alumni provide feedback on every aspect of the students’ professionalism — including how quickly they reached out to set up the conversation. Students also score themselves before, during, and after the 30-minute interview, while alumni do the same. The results reveal either a “positive gap” (when alums score students better than the students score themselves) or a “negative gap” (when the students score themselves better than the alums score them). According to Kessler, the vast majority of students underestimate themselves.
Groo was especially impressed with the speaking skills and maturity of the students. “They had a bunch of interesting questions that were not rote, like a checklist,” she says. “I was very pleasantly surprised with their authenticity and their ability to engage on interesting topics related to our conversation that they couldn’t have known about in advance.”
The mock interviews also reflect the differences between the students’ experiences as undergrads and the alums’ as MBAs. Collin Brown WG99, founder and CEO of nonprofit funding AI tool Sharke, says this was one of the “gaps” he tried to bridge: “When you’re that age, there’s so much you don’t know — and there’s so much you think you know.”
MBAs have the advantage of prior work experience when they arrive on campus, points out Marcia Irwin WG99, a retired investment client portfolio manager and marketing professional. Irwin, like many of the Mind the Gap participants, has kids of her own, which makes her aware of how opportunities have expanded greatly for today’s young people. When she was at Wharton, she remembers, recruiting was limited to two main options: banking and consulting. “If you wanted to do something else, there was really no silver platter being held out to you.”
The Class of 1999 also had the unique challenge of graduating at the tail end of the dot-com boom — which may be relatable to those entering the workforce at the height of another technological revolution. Yu, chief product officer at data storage firm LucidLink, moved back to the West Coast after completing his MBA during the rise of the internet. One of the students he interviewed made a bet with a friend to go “AI-free” for a month because the student felt too reliant on it. “I thought that was incredibly insightful,” says Yu. “That really shows the discipline of Wharton students, that they’re going to push themselves like that. They were conscious of making decisions to step back and look at it from a broader perspective.”
Cora Hsu-Laborde W29 describes Mind the Gap as a “mini-mentoring session with someone who shared my interests.”
Mind the Gap has shown students and alumni alike how AI is changing the priorities for career readiness. Kessler says that with AI dominating the job hunt, human connection is more important than ever: “You don’t differentiate yourself by using a better résumé template. You differentiate yourself by making the most of every time you meet somebody.”
Brown noticed that instead of asking for an introduction to a company, as he remembers doing as a student, students now are asking what skills they need to be successful in the age of AI. “Alumni have a unique perspective because we’re out here, and we’ve failed, we’ve succeeded, we’ve done that journey,” he says. “And sharing that knowledge, especially at a time that’s uncertain for the student, I think that’s super important.”
Alex Xie W29 approached his mock interview hoping to take full advantage of the meeting rather than hastily asking for an internship. “It’s so hard to get time, especially one-on-one time, with alumni,” says Xie. “To really be able to do that for free and to have it in a structured manner was super rewarding to me as a student at Wharton.”
Other students appreciated the structure of the program. Cora Hsu-Laborde W29 says that incorporating Mind the Gap into CR@W allowed her to apply what she learned immediately, “from conducting research before an interview to practicing simple but meaningful gestures, such as sending a thank-you email.”
In March, the inaugural Mind the Gap experience concluded. All in all, 65 mock interviews were conducted among 62 students and 44 alumni. Based on their performance, Kessler and Sosin invited seven participants — including Markowitz, Xie, and Hsu-Laborde — to serve as “GapWell Ambassadors” this summer. That role entails interviewing alumni from around the world for a video series called “Career Confidential.” While Mind the Gap interviews were about building close relationships between students and alumni, Career Confidential involves the ambassadors reporting on various industries and sharing what they glean with other students. So far, Xie has interviewed an asset manager and another alum in private equity.
“A lot of the time, people just go on Investopedia or YouTube to look at a day in the life of these professionals,” Xie says. “But they don’t really get the candid firsthand accounts.” As of July, Career Confidential interviews were on track to be posted on the GapWell website this fall, according to Kessler.
After Mind the Gap’s successful launch, the Undergraduate Division is continuing the program for the upcoming 2026-27 academic year. Many WG99 alumni said they would participate again if given the chance; if more alums from any class year offer to volunteer, the Undergraduate Division aims to extend the program to include second-year students as early as this fall. Students are already looking for more ways to stay involved.
“We have a culture of giving back, but this really cemented that this is a tradition for Wharton alums,” says Xie. “They really give back to the current students. Maybe someday I’ll be a GapWell interviewer.”
