Steppingstone Spotlights

Spotlights 2026

Steppingstone Spotlights

Volume II | Spring 2026

Produced in-house by Steppingstone’s Communications Team

Printed by PrintSynergy Solutions

Meet Our Vibrant Community.

Dear Friends,

As I write to you, the youngest Steppingstone Scholars are embarking on their final projects of fifth grade, and celebrating all their hard work to this point. Reflecting on their child’s very first academic year of Steppingstone programming, one parent remarked:

“I couldn’t be happier with our experience with the Steppingstone program! The support my son has received has been incredible. It has really helped him build confidence and stay on track during such an important school year... Highly recommend.”

The youngest Scholars have started strong, and they have an inkling of the full Steppingstone journey to come over the course of 12 years. Luckily, our tight-knit community of older Scholars and Alumni share stories that allow them, in a sense, to travel through time and see the exciting possibilities ahead.

Over the course of this year, families have seen Scholars thriving at all ages. An eighth grader is exploring new interests at “the independent school of her dreams.” A high school senior created his own nonprofit. College students landed competitive internships. Alumni are executives, strategists, and award-winning leaders.

What do these individuals have in common? They were prepared by Steppingstone to enroll in and make the most of excellent schools. They are attending or have graduated from college. With each and every pursuit, they show the Scholars of tomorrow what is possible.

With deep appreciation for you—and for all that you do to make 12 years of tuitionfree programming possible—please join me in celebrating their stories.

Gratefully,

Kelly D. Glew President & CEO Steppingstone

Scholars

Kyelle M. Is Writing Her Own Story

Many eighth graders feel intimidated by the blank page of an unwritten essay. But Kyelle, a Scholar attending Noble and Greenough School, finds writing “a relaxing pastime” that takes her “to another world.”

With plans to become a published author before she turns 20, she is already drafting her first novel. The novel is about a girl torn between the expectations placed on her and the life she wants for herself.

Kyelle’s Steppingstone journey has helped her find a perfect match school, her best friend, and a community that is supporting her on the path to realizing her dreams.

Finding an Excellent School, and Much More

Before enrolling at Nobles, Kyelle attended public school in Boston, where she often found herself unchallenged. Her fourthgrade ELA teacher recognized her potential and nominated her for Steppingstone. The application process—interviews, testing, and preparation—was demanding.

Kyelle rose to the academic challenge at Steppingstone and hasn't looked back. From Kyelle’s best friends to her Steppingstone Advisors, she has a community of people that support her: “I made so many great relationships and really enjoyed the community that I got to foster at Steppingstone. I appreciate that Steppingstone takes the time to get to know the students who are a part of the organization.”

Finding the right fit when choosing which school to attend is key. Kyelle shared how Steppingstone helped her find her way to

Nobles. “When my Advisor introduced me to Nobles, I knew right away that I could make my way in the Nobles community. I was also compelled by the fact that it is a huge campus and there are so many opportunities to be yourself. My school is high energy, and I’m also high energy, so I fit right in.”

When it comes to fitting in at school, it never hurts to have your best friend by your side. Kyelle found her best friend Vicky at Steppingstone, who also attends Nobles. Kyelle says that Vicky always pushes her to be her best self—all while having fun. “Through Steppingstone, I've made friends who are just as invested in their future as I am in mine.”

Taking Chances

Beyond excelling in her academics, Kyelle also is involved in extracurriculars like cross country and drama club.

“Steppingstone doesn’t just encourage Scholars to pursue academic excellence. It also encourages you to pursue your interests and opportunities that will help you grow as an individual.”

Kyelle embraces new experiences with zest and optimism. After trying out for the wrestling team and deciding that it ultimately wasn’t the right match for her, she still looks back on the experience as a positive lesson.

“If I could offer younger Steppingstone Scholars some advice, I would tell them to take chances by trying out the various opportunities life has given them. To join that new club, try out for the basketball team, or apply to the independent school of your dreams. The worst possible scenario is that you find out that that thing is not right for you. The best-case scenario is that you now have a new hobby or go to a really great school. New opportunities are always waiting for you.”

Unleashing Individual Potential

Steppingstone’s 12+ year journey fosters an environment for Scholars to achieve the future they seek. “In my view, Steppingstone represents more than a program designed to assist children from Boston in finding improved educational opportunities. It embodies a community of individuals collaborating to ensure that we all achieve success in our unique ways.”

For Kyelle, this is only the beginning of her successes! Through high school and college, career preparation, and maybe even the best sellers list, we can’t wait to see where she goes, and to be there for her every step of the way. ●

Daniel I.

A senior at Boston Latin Academy, Daniel has kept busy with applying to colleges, serving as class president, launching new extracurriculars, and... founding his own financial literacy nonprofit, Fortune Avenue.

The organization “seeks to protect and empower the same way Steppingstone did and currently does for me. Steppingstone’s support has stayed consistent and strong from fifth grade to the present day.”

Daniel paid it forward to the next generation by creating a financial literacy elective for middle school Scholars. He explains, “over the course of three weeks, students learned about budgeting, explored the fundamentals of investing (and how important it is to invest in yourself), and worked through career exposure activities.”

After securing a SuccessLink grant of $27,000, Daniel now plans to hire 10 young people to support his programming for Boston students over the summer.

Melissa G.

An alumna of The Winsor School, Melissa studies business, sociology, and economics as a Traquina Scholar at Brandeis University. With Steppingstone’s support, Melissa found her first asset management internship at Leeward Investments. She then landed her current client services internship at Income Research + Management, a Steppingstone corporate partner.

This summer, Melissa will join Wellington Management Company as part of the Business Undergraduate Summer Intern Program. She looks forward to building on her experience and exploring the field of private investment management. She shared in a recent LinkedIn post, “This opportunity would not have been possible without the support of [Steppingstone board member] David A. Chang, who has been a mentor to me and a constant source of guidance throughout this process. I am also grateful to Steppingstone for their role in helping me reach this point.”

C.

An alumna of Ursuline Academy, Leila is now preparing to graduate from Northeastern University with a bachelor of science in business and finance. While at Northeastern, Leila took full advantage of their co-op program, gaining valuable work experience in fund reporting at GMO, a global investment management firm.

She has also prepared for her career as a member of Steppingstone’s near-peer mentoring program, STRIVE (Scholars Thriving through Relationships, Internships, and Valuable Experiences).

“Steppingstone is providing me with a lot of tools and unique opportunities that I would not have had readily available otherwise. Whether it is resume review or networking opportunities, it has broadened my scope within my chosen career field. Getting a chance to speak with professionals within the field I want to go into has been extremely helpful. My STRIVE mentor gave me a lot of tips and tricks and things to look out for as I go down my path—things he would have wanted to know himself.”

Malcolm H.

Today a middle school Scholar at Beaver Country Day School, Malcolm expressed dreams of one day becoming an NBA Player, a patent lawyer, or perhaps an entertainment lawyer. He is still weighing his options, and a Steppingstone visit to the new U.S. headquarters of The LEGO Group, facilitated by Board of Young Professionals member Isaac Levy, gave him exciting new ideas.

“When I came here, it really made me expand my creativity,” he realized. “I want to build creativity into my future, maybe even working here in the LEGO office. Maybe designing, or even testing. I think this visit will impact my future on what I want to do.”

With Steppingstone’s Career Success curriculum spanning fifth grade through college graduation, Malcolm will have plenty of opportunities to continue exploring. “The way that my Advisor supports me has been a really big help…he has kind of helped me work better and do the things I want to do.”

Alumni

Esteban Gutierrez-Alvarez ’12: A Journey from Steppingstone to Judicial Courtrooms

Esteban Gutierrez-Alvarez ’12 joined Steppingstone 15 years ago because his mother had a vision for his future.

“She wanted me to have what she called a life-changing opportunity: a network of teachers and advisors who could push me to aim higher.”

Today, Esteban affirms: “Steppingstone delivered.” The graduate of Milton Academy and Harvard University—and soon, Columbia Law School—has accepted an opportunity to serve as a judicial law clerk to the Honorable Elizabeth N. Dewar of the Massachusetts Supreme Judicial Court.

“Law always made sense to me.”

Looking back on his application to Steppingstone, Esteban found a younger version of himself “wanting to help others and make sure my peers and community would benefit from my work.”

As a J.D. candidate at Columbia, Esteban has learned much about United States legal institutions. He keeps coming back to the core lessons he learned at Steppingstone: “about persistence, about community, about using whatever position you hold to help others."

Finding His Place at School

Steppingstone first prepared Esteban to gain admission to Milton Academy. Our evidencebased programming for college access and

career readiness relies on this key step: helping families to identify and apply to rightfit schools that will lead to college.

“The adjustment was hard at first,” Esteban remembers. “I felt like an outsider, and I leaned on my Steppingstone Advisors to help me find solid ground. Eventually, I did. I fell in love with my classes, performed in many plays and musicals—a highlight includes the role of Lord Farquaad in Shrek: The Musical and captained the Speech and Debate team.”

Esteban’s time at Milton prepared him for admission to Harvard. While settling into his first semester, he noticed feelings of imposter syndrome creeping back. “I found myself surrounded by enormous resources and opportunities, but I struggled to figure out how to access them and how to take full advantage of what Harvard had to offer.”

Steppingstone was there to guide him. “Conversations with Annie Wu and other Advisors helped me understand that I belonged at Harvard and showed me how to navigate the institution. They helped me see that the skills Steppingstone had built in me—the confidence to ask questions, the willingness to seek help, the determination to push through uncertainty—were exactly what I needed.”

This led to a transformative four years, studying under leading scholars in law, classics, political science, and music. In his senior year, Esteban served as the 165th president of the Harvard Glee Club: the oldest collegiate chorus in the United States.

“When we invest in Steppingstone Scholars, we not only help them access opportunity. We create professionals who carry this community’s values into courtrooms, classrooms, hospitals, and boardrooms across the country.”

Impacting the Courts, and the Next Generation of Scholars

As Esteban celebrates the milestone of earning his J.D. this spring, he looks forward to launching his career—building on previous opportunities as a summer associate at Ropes & Gray LLP and judicial extern to the Honorable Kiyo A. Matsumoto of the U.S. District Court for the Eastern District of New York.

After Esteban’s clerkship at the Massachusetts Supreme Judicial Court, he will return to Ropes & Gray: “a firm that has shaped the legal landscape in Boston and nationally for more than a century and continues to handle some of the most consequential legal matters of our time.”

Even as he fulfills many of the goals he set as a Scholar, Esteban remains committed and connected to Steppingstone as an Alumnus. He explains, “Steppingstone’s impact lasts through every stage of a career and a life I look forward to giving back to the next generation. I want to hear from current and future Steppingstone Scholars who have questions about careers or need advice. That is how this network works: each generation lifts the next.” ●

In 2026, Steppingstone hosted its inaugural Alumni Exchange networking event. Alumni participated in a moderated discussion about career success. Get to know the panel and explore a few of their insights.

Dr. Agnes Oyewale ’03

Alumni Exchange Panel Moderator

Director of Career Services & Employer Relations and Adjunct Instructor at Fisher College

John D. O’Bryant School of Mathematics and Science, Centre College (B.A.), Northeastern University (M.S., Ed.D.)

David Medina ’99

Senior Cyber Threat Intelligence Consultant at Recorded Future

Noble and Greenough School, College of the Holy Cross (B.A.), The George Washington University (M.A.)

For leadership in anti-trafficking policy: Winner of the Ohtli Award from the government of Mexico; Presidential Service Award for work with the Colombian Ministry of Foreign Affairs and the U.S. Department of State

“Our perception of career success will change depending on what stage of life we’re in. Success for me now is mental health, balance, and financial stability.”

Offiong Bassey ’97

Executive Leader, Strategist, and Creative; Founder of Bassante Advisory Group

Noble and Greenough School, Yale University (B.A.)

RevBoston Top 20 Female Tech Leader; Selected for McKinsey’s Executive Leadership Program; Former Global Vice President at Dell Technologies

“Your seat at the table is intentional. There’s purpose for you in that room. You don’t have to know everything — no one at that table holds all the answers, and that’s why your perspective matters.”

Max Clermont ’01

Public Affairs Leader at Vertex Pharmaceuticals

Boston Latin Academy, Brown University (B.A.), Brown University School of Public Health (M.P.H.)

Board member, Bottom Line and Just A Start; Advisory Board member, the Center for Comprehensive Healing at Mass General Brigham

“Pivoting doesn’t mean you’re lost—it means you’re learning; it’s clarity in motion.”

Thank you to all who show leadership and volunteer their time for Steppingstone’s success.

Board of Directors

Sara Fuentes Anidi ’95 Area Director for Metro Boston, Massachusetts Department of Mental Health

Todd Bland

Senior Consultant & Executive Coach, Carney Sandoe & Associates

Jennifer Block

Susan Jefferson Boney

Donavan D. Brown ’95, Clerk Vice President, Monticello Associates

Alixe Callen Head of School, Milton Academy

David Chang Partner, Wellington Management Company

Rafael Cofiño Managing Director, Great Hill Partners

Erin Condron

Brian J. Conway Senior Advisor, TA Associates

Betsy Lind Danziger Lower School Admissions Associate, The Fessenden School

Mary Driscoll Educator

Fabian Fondriest, Treasurer Executive Chairman, TRUE

Jennifer Fulton Executive Vice President, Bain & Company

Kate Gilbane

Jonathan M. Goldstein Senior Advisor, TA Associates

Robert P. Henderson, Jr., Chair Education Consultant, Resource Group 175

Isabelle Loring

Sofia Teixeira Mistretta ’94 Senior Director, Culture, Vertex Pharmaceuticals

Mark S. Morrow

Editor At Large (ret), The Boston Globe

Dr. Stephanie Pinder-Amaker Vice Chair, Engagement & Enrichment, McLean Hospital Founding Director, McLean College Mental Health Program Associate Professor of Psychology, Harvard Medical School

Darian Reid ’99

Director of Studies, Director of Strategic Initiatives, The Roxbury Latin School

Alex Sacerdote

Founder and CEO, Whale Rock Capital Management

John G. Simon, Co-founder Managing Director, Sigma Prime Ventures

Perry Traquina

Former Chairman and Chief Executive Officer, Wellington Management Company, LLP

Jenny Weymouth

Douglass Williams Chef/Owner, MIDA & APIZZA

Natasha Telesford Williams, Vice Chair

Chief Financial Officer, City Fund

President's Council

Bart Epker Healthcare Investor

William Fitzsimmons, Ed.D Dean of Admissions and Financial Aid, Harvard College

Chris Gabrieli

Chairman of the Massachusetts Board of Higher Education, CEO of Empower Schools, CoFounder of Transforming Education

Blair Hendrix Partner, Bain Capital Private Equity

Pamela R. Holding

Former Co-head of Equity & Asset Management, Fidelity Investments

Joanna Jacobson

President & Trustee, One8 Foundation

Karl Reid, Ed.D

Author, Working Smarter, Not Just Harder: Three Sensible Strategies for Succeeding in College...and Life

Jill Shah

President, The Shah Foundation

Rachel Skerritt

Chief Strategy Officer, Attuned Education Partners Vice Chair, Boston School Committee

Hilary Nicholas Steinert

Ted Wendell Retired

Board of Ambassadors

Isabelle T. Black

Linda Borden

Katie Bramley

Danielle Bynoe ’04

Susanne Chiang & Dr. Vincent W.

Chiang

Melanie Chiverton

James Coughlin

Heidi Crean

James Danziger

Betsy & Rick Edie

Alexis Egan

Lee Englert

Alex Fine

Brittney Gammell, Co-Chair

Debbie Gelb

Char Joslin & Les Cheek

William N. Kring, PhD & Karen

Chan Kring

Senam Kumahia ’96

Elizabeth Kumin

Kate Lubin

Laura Morris, Co-Chair

Mindy Munger

Sarah Reynolds

Debby Robbins

Rachel Rock

Ani Sacerdote

Matt Santangelo

Josh Schultz

Rachel Segall

Brent Edward Shay

Rob Small

Kathryn Zioto & Fred Borges

Board of Young Professionals

Ashley Andrade

Jill Booth

Nicki Brill, Co-Chair

Parker Catlett

Merry Chin '05

Andrew Conway

Naveen Chokkar

Olivia Corkery

Charlie Danziger

Hayley Edgerley

Clarissa Elliott

Aylin Feliz '07

Benjamin Hack

David Henderson

Patrick Henderson, Co-Chair

Jenna Isaacson

Josh Levine

Isaac Levy

Felix Liang '06

Henry Liang '10

Margaret Mahoney

Rahim Malik

Eliza McGinn

Cheeznah Milord

Brayden Minahan

Christian O'Connor

Chris Philbin

Akash Prasad

Will Sharton

Charlie Sharton

Stephen Smiddy

John Van Allen

Sebastian Viasus '07

Nina Walat

Taylor Walshe

Alexandra Watson

Peter Wu

Shihua Wu '10

Alumni Council

Lois Abdulai ’93

Hannah Foell ’94

Jamilah Ryan ’95

Joy Kogut ’96

D'Lynn Jacobs ’97

Cindy Nguy ’97

Patrick Costello ’99

Martina Durant ’99

Dalinda Ifill-Pressat ’99

Laniesha Gray ’00

Nyadenya Inyagwa ’00

Max Clermont ’01

Jennifer Pierre ’01

Ebele Anidi ’02

Mohammed Alkhafaji ’03

Thomas Tsui ’03

Danielle Bynoe ’04

Abimbola Cole ’04

Miranda Haymon ’05

Raven Rankine ’05

Alcina Tran ’05

Daniella Colombo ’06

Tyrone Li ’06

Felix Liang ’06

Aderonke Odewale ’06

Fehintola Abioye ’07

Sidney Bowden ’07

Henry Kwan ’07

Tiffany Xie ’07

Bassil Bacare ’08

Stoni Drane ’08

Cecilia Morales ’08

Kim Romero ’08

Derek DaSilva ’09

Ope Olukorede ’09

Nick Palermo ’10

Denny Yu ’10

Tashayla Borden ’11

Fiona Phie ’11

Madusa Sidibay ’11

*As of May 2026

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