Match Central Office Team


Ms. Ariwodola was born in Nigeria but moved to New York City in her early teens. She attended University of Maryland, Baltimore County, where she earned a degree in Biological Sciences. Upon graduation, she decided to accept the opportunity to work at Match as a tutor. Her experiences that year sparked her interest in School Operations. In her free time she enjoys running, reading and watching Korean dramas.


Jennifer Berylson Block | General Counsel

Ms. Block joined Match in March 2012 as the General Counsel.  Previously, she worked at the law firm of Goodwin Procter LLP from 2005-2012, as a member of the Private Equity group, primarily focusing on mergers and acquisitions, private equity transactions, corporate governance matters and the representation of early-and later-stage growth companies.  She also represented a large number of not-for-profit clients and played a large role in the firm's pro bono initiatives. Ms. Block received her B.A. from Williams College in 2001 and her J.D. from the University of Pennsylvania Law School in 2005.  She is admitted to practice in Massachusetts.


Richard Dragon | Controller

Mr. Dragon is a Boston native who has been a CPA since 1992. Mr. Dragon is a 1990 graduate of Bryant University. His practical accounting and auditing background comes from working in the Providence office of Ernst and Young LLP from 1991 to 1995, and at a local Providence firm from 1995 to 1997. He then became self-employed in order to self-publish a book on R.I. history and remained on his own until becoming involved with Boston charter schools in 2004.  


Jahfree Duncan | Director of Technology

Mr. Duncan graduated from Brandeis University in 2009 and began at Match as a 10th grade US History TA as a member of the Match Corps. He has been on the Match Operations team since then and is now the Director of Technology. He graduated from Tufts University’s School of Engineering with a Master’s of Science in Engineering Management in 2016 and is looking forward to continuing to work and grow in the education, technology, and management sectors.


Ms. Fofana is from Boston, MA. She graduated from Simmons College with a Bachelor of Arts in Communications. Before joining Match, Ms. Fofana taught preschool and prekindergarten at the M.I.T David H. Koch Technology Childcare Center. Previously, she worked as a technology assistant for five years in the Information Technology Department at Simmons College. 


Orin Gutlerner | Chief academic officer

Prior to his role as the CAO of Match Schools, Mr. Gutlerner was the founding Director of the Match Teacher Residency and Sposato Graduate School of Education for eight years.  Before that, he spent five years at Harvard University's Graduate School of Education working to re-shape the Undergraduate Teacher Education Program and acting as a guest lecturer in the Graduate School.  Before his work at Harvard, he oversaw Alternative Teacher Recruitment and Training programs for the Massachusetts Department of Elementary and Secondary Education.  Mr. Gutlerner holds a Master of Education degree from the Harvard Graduate School of Education.


Tobey Jackson | Chief talent Officer

Mr. Jackson is originally from Providence, RI.  He has a Bachelor's degree from Brown University and a Master's degree from Harvard University's Graduate School of Education.  After teaching middle school science and math in independent schools, Mr. Jackson joined Boston Collegiate Charter School as a founding science teacher.  He later served as the school's middle school director/principal for seven years.  Most recently, Mr. Jackson has been an educational consultant, including working with Boston Collegiate Charter School and Match on facility acquisition and renovation.


Rachel Johnson | Director of records and Enrollment

Ms. Johnson graduated magna cum laude from Rutgers University in NJ, with a concentration in Sociology and Anthropology.  She enjoys being active and shares a love of Ultimate Frisbee with her family and close friends.

Stig Leschly | Chief Executive Officer

Mr. Leschly is the CEO of Match's related entities -- Match Public Charter School, The Charles Sposato Graduate School of Education, and The Match Foundation, Inc.  Prior to joining Match, Mr. Leschly was the founder and managing partner of the Newark Charter School Fund.  The fund supported the charter school sector in Newark, NJ and advanced reform of Newark's public school system during the first term of Mayor Booker.  Prior to his work in Newark, Mr. Leschly was a full-time lecturer at Harvard Business School where his teaching and research focused on entrepreneurship and education reform.  In the late 1990's, he was the CEO and founder of, an early competitor to that was acquired by Mr. Leschly has a  BA in Comparative Literature (Summa Cum Laude) from Princeton University, a JD from Harvard Law School, and an MBA from Harvard Business School.


Laura Mahajan | Director of Coaching, Match Teacher Residency

Prior to her role in designing the MTR program, Ms. Mahajan was a Social Studies teacher in the KIPP middle school in Harlem, NY.  She began her career as a Match Corps tutor, and holds her Master of Arts in Teaching from Teachers College at Columbia University, and an A.B. from Princeton University.


Stacy O'Toole | Director of Training, Match Teacher Residency

Ms. O'Toole was the founding Head of Blackstone Valley Prep middle school in Rhode Island.  Prior to that, she worked for Democracy Prep charter schools in Harlem, as a teacher and director of culture and enrichment, where she was Teacher of the Year.  She holds a Master's Degree in Libary Science from Queens College, a Master's Degree of Teaching and Curriculum from Harvard, and a B.A. from Tufts University.

david steefel-moore | operations director and deputy to Chief operating officer

Mr. Steefel-Moore is Operations Director and Deputy to the COO.  Prior to joining Match's Operations team, he worked in a variety of roles related to education reform, public health, and political advocacy, and was a member of Match Corps IX at Match High School.  He holds a B.A. from Carleton College and an Ed.M from the Harvard Graduate School of Education.

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Ashley Danoff Sweeny | Director of Grants and Compliance

Ms. Sweeny graduated from New York University in 2002 with a B.A. in International Relations, Italian, French, and Japanese.  She also received a M.A. in Sociology of Education from Boston University in 2004.  Ms. Sweeny was a member of Match Corps 1 at the Match High School.


Nnenna Ude | Chief operating officer

Ms. Ude is a Boston native who attended Boston Latin School and then Dartmouth College. While at Dartmouth, she majored in Psychology and devoted a significant amount of her time to advancing minority recruitment initiatives. Since her graduation from Dartmouth, she has worked in education and hospitality, including helping to run her family's restuarant.  She considers it a privilege to be able to serve students and families from her city and is committed to helping our students succeed in and out of the classroom.  Ms. Ude served as the Director of Operations at Match Middle School for two years.


Dr. Annie Weiss graduated with a B.A. from Williams College and obtained her Ph.D. in Psychology from Tulane University. She completed her clinical residency at Boston University Medical School at the Center for Multicultural Training in Psychology. Subsequently, she completed a post-doctoral clinical fellowship at Harvard Medical School where she specialized in the treatment of children and adolescents with acute and chronic mental illness. Dr. Weiss is a former New Orleans Public School teacher and has a particular interest in helping students and teachers cope with the demands and stressors in the school environment.  Most recently she was the Director of Psychological Services at Sci Academy, a charter school in New Orleans.