Wes Updike, a Cambridge, MA native, is passionate about empowering students to reach their full potential and capitalize on their college experiences. A graduate of Cambridge Rindge and Latin High School, Wes went on to earn his degree in English from Trinity College, where his love for literature and learning deepened. Before joining Steppingstone as Director of College Success, he spent nearly six years as an academic advisor at Duet, guiding students through their academic journeys and helping them achieve their educational goals. Outside of work, Wes loves playing and watching soccer (preferably Arsenal), diving into a good book, traveling, and exploring new cultures and ideas.

Robert joined the Steppingstone team in 2022. He received his B.A. in sociology and Italian studies from College of The Holy Cross in 2022. Robert grew up in East Boston, MA, and currently resides in Revere. He served as a student mentor and tutor at several community organizations in Worcester and also became a member of several student organizations on campus during his time in college. He appreciates the opportunity to be working with a group of hardworking Scholars who are committed and willing to grow. During his free time he enjoys biking, hiking, reading, exploring different foods.

Louisa earned her B.S.W. from Salem State University in 2020. Before joining Steppingstone, she worked as a Child Services Coordinator for Victory Programs Inc., a sober-living residential program for families in Boston, and later as a Teaching Assistant at Wellesley High School. Her passion for working with young people and helping them achieve their educational goals led her to join the College Success Team. In her free time, Louisa enjoys exploring Boston, listening to music, and spending time with her cat, Ghost.

Lee joined Steppingstone in 2024 as a High School Success Advisor. Lee grew up in Massachusetts, and attended college at Washington and Lee University in Virginia. She graduated in 2020 with a B.A. in economics and politics with a minor in educational policy. Lee stayed in Virginia for four years upon graduation where she first worked for an Americorps program as a College Advisor and then served as a Student Success Coach at a university. Lee is excited to be a Massachusetts resident again and to return to Steppingstone as she served as an intern with NPEA between her Sophomore and Junior years of college! Lee enjoys reading, spending time outside, and meal prepping!

Katie moved from traditional education and Long Island to join Steppingstone in Boston as a Social Emotional Learning Associate in 2023. She received a B.A. in history and a teaching certification from Roanoke College in 2018 . She has previously worked as a social studies educator teaching students from 6th to 12th grade. Katie firmly believes that SEL makes a difference in children’s lives, and looks forward to learning more about Boston, aiding the Steppingstone community, and seeing Scholars' success! In her free time, Katie enjoys spending time with her black labrador, Goose, reading fiction books, and cheering on her favorite NY sports teams.

Sydney Corcoran joined Steppingstone in the Fall of 2024. Originally from Western Massachusetts, she moved to Boston to attend college, where she earned a B.S. in education and human development with a specialization in youth development and justice from Boston University. Sydney is excited for the opportunity to work with and support scholars and their families in achieving their academic and career goals. Outside of work, Sydney enjoys practicing yoga, painting, and spending time with friends and family!

Leocadia graduated from Regis College in 2020 with a B.S. in Biology. She's lived in Boston her entire life, specifically Dorchester. Leocadia is a former Steppingstone Scholar! Outside of work, Leocadia enjoys art, music, and spending time with her family and friends.

Anna earned her B.S. in Psychology from Salem State University and is currently completing her final year at Merrimack College, where she is pursuing a Master’s in School Counseling. Before joining Steppingstone, she worked as a student success coach at Franklin Cummings Tech, and prior to that, as an educational advisor for the TRIO Talent Search Program at Lynn English High School. Anna is thrilled to be a part of the College Success Team, where she looks forward to helping students achieve their academic and personal goals. Her guiding principle is: “I am not here to pass judgment or dictate your path. I am here to collaborate with you in identifying your goals and devising a plan to achieve them.” Outside of work, Anna enjoys cooking and baking, spending time with friends, and exploring new places through travel.

Sam is a first-generation Haitian American graduate of Bates College, where they earned their B.A in Africana studies with a concentration in racisms. They joined Steppingstone in 2023 as a Middle School Success Advisor, committed to enhancing student experiences and helping first-generation, low-income students—just like themselves— to turn their dreams into reality. As an experienced  DEIB facilitator and educator, Sam has partnered with Somerville Public School District, Bates College, and the Thrive Scholars Program (of which they are a proud alumni) to lead conversation on identity, access, belonging, liberation, and BIPOC joy. Outside of work Sam can be found cuddled up with a good book, writing prose, thrifting at their favorite spots, or cooking Caribbean food with friends!

To learn more about Sam, or read their work, feel free to connect with Sam on LinkedIn!

Thai has been with Steppingstone since 2019. He graduated from the University of Hawaii with his B.A. and M.A. in English. He enjoys working with College Scholars and getting to learn more about their goals and aspirations. When he is not working, Thai is a huge anime fan and loves his Lakers! Currently, Thai is working fully remote from California!

Sean graduated from UMass Boston in 2021 with a B.A. in Exercise and Health Science. Before that, Sean graduated from Boston Latin School in 2016. During undergrad, Sean started working at a nonprofit in Dorchester called Viet-AID where he developed his passion for helping young people prepare academically for their future. Outside of work, Sean loves finding new restaurants to try with his friends, watching Boston sports, and reading any and all genres of books.

David Meneses Ontiveros is member of the Steppingstone Commencement class of 2012, and became a Middle School Success Advisor in 2023. After commencing from Steppingstone, David went to the Fenn School for middle school and then Roxbury Latin for high school. He attended Connecticut College and graduated with a double major in psychology and Latin American and Latino studies. In college, David held numerous executive board positions for various clubs, and worked in the admissions department for two years. Outside of work, David likes to hangout with his friends and watch and play sports.

Originally from Fairfield, Connecticut, Dan joined Steppingstone in October 2022 after teaching in the Greater Boston Area for several years. He earned a B.A. in English secondary education from Providence College. As an Advisor, Dan strives to create a culturally responsive academic environment that celebrates intersectionality and inspires a passion for learning, literature, and civic engagement. In his free time, he enjoys playing the saxophone, writing short stories, and playing soccer.Originally from Fairfield, Connecticut, Dan joined Steppingstone in October 2022 after teaching in the Greater Boston Area for several years. He earned a B.A. in English secondary education from Providence College. As an Advisor, Dan strives to create a culturally responsive academic environment that celebrates intersectionality and inspires a passion for learning, literature, and civic engagement. In his free time, he enjoys playing the saxophone, writing short stories, and playing soccer.

Kat joined Steppingstone in 2013 as an Advisor. She later served as the Director of Admission and the Senior Director of Middle School Success. Prior to joining Steppingstone, Kat interned at Boston Chinatown Neighborhood Center's youth program, and at the Museum of Science conducting K-12 engineering education research. She first served Boston Public School students through Project Destiny ministries at the Boston Chinese Evangelical Church. Kat received her B.S. in Chemical Engineering from Cornell University. Outside of work, she participates in ballet classes, mentors college students at her church, and listens to BTS.

Chris is an experienced educator with a demonstrated history of leading start-up initiatives in the field of education. Skilled in program development, Chris' expertise lies in the development and management of innovation within ​the social sector. Prior to joining Steppingstone, Chris served as Academic Dean for the Trinity Boston Connects’ TEEP program, as well as band and orchestra director at the Boston Arts Academy. Chris received his B.M. in Music Education from the Berklee College of Music and M.S. Ed. in Education Entrepreneurship from the University of Pennsylvania.​ Chris serves as a trustee on various school and nonprofit boards including The Meadowbrook School and Hartford Youth Scholars.

Bianca graduated from Boston College in 2019 where she earned her B.A. in Elementary Education and Applied Psychology & Human Development. She then went on to get an M.Ed in Special Education at Boston College where she was a Donovan Urban Teaching Scholar. Before coming to Steppingstone in 2022, Bianca was a fourth grade teacher in Boston Public Schools. Bianca loves getting to work with and support the amazing Scholars and their families. She also loves seeing the Scholars grow both academically and socially. In her free time Bianca loves to read, cook, bake, paint, and hang out with friends.

Will brings varied experience and expertise from over a decade in education to his role as Director of High School Success at Steppingstone. He has worked as a classroom teacher, math department lead, and house chair at schools in both Los Angeles and Boston, as well as Director of Partnerships for an early college STEM pathways organization. He brings a student-first mindset to his work and has a grounding belief that all students can be successful when they can meaningfully explore a variety of career paths and receive individualized support and mentorship along the way. Will received a BBA from George Washington University and an M.Ed. degree in educational leadership, organizations, and entrepreneurship from the Harvard Graduate School of Education. In his free time, he enjoys chasing his dog, trying new recipes, and finishing 80% of crossword puzzles.

Ailyn joined Steppingstone in 2023 and supports both the Admission and Academy teams in her role. She is a Steppingstone Alumna and first-generation college graduate, receiving her B.A. in feminist, gender, and sexuality Studies from Stanford University. In her role, she looks forward to learning from and supporting the Steppingstone community throughout the first chapters of the Scholars Program journey.

Mary Clare Scalise (she/her/hers) joined Steppingstone in the fall of 2024 as a Middle School Success Advisor. Mary Clare is a proud Midwesterner at heart, but came to Boston in 2019 for college and has stayed since! She graduated from Boston College with a degree in applied psychology and human development and has experience with teaching and advancement at independent schools in the Boston area. She is passionate about having roles where she can build strong and supportive relationships with students and is thrilled to be on the Steppingstone Team! She loves the restorative approach and social-emotional aspects of the Steppingstone curriculum. In her free time she loves zumba, working with animals, and drinking coffee.

Mary received her B.A. in Sociology and Spanish Literature from Colgate University and her M.A. in Elementary Education from Sacred Heart University. Mary worked at Steppingstone for three years as a Reading and Writing teacher prior to joining the team full time in 2012. Throughout her time here, she has served as an Advisor, a member of the Teaching & Learning team, and Director of Preparation & Placement. Now focused on placement across the organization, Mary is thrilled to help Scholars and families access new educational opportunities.

Sarah joined Steppingstone in 2024 as Impact & Evaluation Specialist. Prior to joining Steppingstone, she worked at Boston After School & Beyond as Measurement & Improvement Coordinator, supporting out-of-school time programs with data collection and integrating findings to improve program quality. Previously, Sarah also served as a teacher for the New York City Department of Education, where she taught Spanish to 6th and 7th graders in Brooklyn and helped launch her school’s Spanish program. Sarah holds a B.A. in Spanish and Education from Tufts University and a M.S.Ed. in Secondary Spanish Education from The City College of New York. Outside of work, she enjoys baking, traveling, and spending time outdoors.

Yamiles or “Yami” is an Academy Advisor for Steppingstone Scholars and families. She is Dominican, but New York born, and Boston raised. Yami graduated from Massachusetts College of Liberal Arts in 2018 with a B.A. in Sociology and Child and Family Studies. She loves traveling, listening to music, and spending time with family and friends very much! She is a very passionate Latina dedicated to giving back to her community by cultivating the opportunity for growth, learning, and success for youth of color.

Kylie joined Steppingstone in 2023. She graduated from Boston Latin School in 2016, where Kylie, along with her classmates, led and participated in a student led social justice campaign known as #BlackatBLS. This campaign led to a reevaluation of the exam school admission process. Kylie's commitment to social justice and passion for education led to her completing her B.A in sociology and Africology at Temple University, and then completing her M.Ed in secondary education with Boston Teacher Residency, through the University of Massachusetts Boston. In her free time, she enjoys traveling to new places and attending music festivals.

Dess is a first generation Guyanese American graduate of Hampshire College, where they earned their B.A in Black history, psychology, and theatre. They are currently pursuing an MFA in Drama Therapy from Lesley University. Originally from Brooklyn, New York, Dess moved to Massachusetts in 2016 and has lived here ever since! Dess joined Steppingstone in 2024 and currently serves as an Academic Advisor for upper elementary Scholars. Being first generation is important to Dess and they are excited to work with similar students and their families to help them reach their goals. Outside of Steppingstone you can find Dess immersed in the arts! Photography, pottery, music, painting, creative writing, you name it!

Annie joined Steppingstone in 2015 as an Advisor to middle and high school Scholars before transitioning to work with college Scholars. Prior to joining Steppingstone, she coordinated academic and enrichment programs for youth at a different organization, and supported undergraduate students in navigating the college experience at her alma mater. Annie received her B.S. in Elementary Education from Boston University. Outside of work, she enjoys playing with her dog (Milo) and baking (while very roughly following recipes).

Molly joined Steppingstone in 2024 as their Director of Placement. She received her Ed.M. in education leadership, organizations, and entrepreneurship from the Harvard Graduate School of Education. Molly's experience includes teacher training, student advocacy, international teacher development, restorative re-engagement practices, curriculum creation, and independent consulting. She has been an instructor of Waldorf 1st grade, credit-recovery high school English, water safety, and the performing arts. Additionally, she has served on both K-8 and international school boards. One of her greatest passions is exploring the field of educational ethics, with the hope of contributing moral growth strategies for more accountable school leadership.

Catherine joined the Steppingstone team in 2024 as the Director of SEL. She is passionate about promoting mental health and creating safe spaces for both Scholars and staff. She has former experiences working in areas of emotional regulation, neurodevelopmental challenges, and trauma. She previously worked as a clinical social worker in community health centers and schools. She received her M.S.W. from Boston College, and received her B.A. in Psychology from Rutgers University. Outside of work, Catherine enjoys musicals, yoga, and the beach.