Home > Gulliver Appoints Dr. Tom Milaschewski as Next Head of School
Gulliver Preparatory School is pleased to announce the appointment of Dr. Tom Milaschewski as its next Head of School, effective July 1, 2026.
Following a comprehensive national search, Dr. Milaschewski was selected for his deep commitment to instructional excellence, student well-being, and leadership that strengthens both academic outcomes and community culture. He brings to Gulliver a track record of guiding schools through periods of growth and change with clarity, care, and purpose.
“We are thrilled to welcome Tom to Gulliver,” said Gulliver’s President, Simon Hess. “He is an educator whose values, vision, and leadership align powerfully with our commitment to Next-Level Teaching and Learning and to nurturing Thriving Students. Tom’s arrival ensures continuity of excellence as we build on Gulliver’s extraordinary legacy and look ahead to Gulliver’s next chapter.”
Tom joins Gulliver from Reading Public Schools in Massachusetts, where he currently serves as Superintendent, leading a high-performing district of more than 4,000 students and 800 faculty and staff across nine schools. Under his leadership, the district has advanced outcomes in literacy, STEM, college readiness, and innovative career pathways spanning computer science, engineering, healthcare, and the arts.
A former teacher and principal, Tom is widely recognized for his collaborative leadership style, ability to build strong partnerships with families and boards, and focus on empowering educators to do their best work on behalf of students. His approach reflects Gulliver’s belief that success is measured not only by what students achieve, but by who they become along the way.
“I’ve been incredibly impressed by the people in this community and the shared sense of purpose that connects them, along with the care shown for students,” said Tom. “Gulliver is a unique and deeply credible institution with an outstanding reputation, and I’m excited to begin listening, learning, and forming relationships as we carry forward the school’s strong foundation and proud traditions.”
Tom earned his doctorate from the Harvard Graduate School of Education and has dedicated his career to building learning environments where high expectations, care for the whole child, and a strong sense of belonging go hand in hand. Throughout his career, he has focused on creating school communities where students are both well supported and challenged to grow. His leadership reflects a belief that strong outcomes are built through aligned instruction, meaningful relationships, and a culture where students and educators alike can thrive.
Tom and his wife, Sarah, are the parents of five children: Makenna (12), Olivia (10), Jocelyn (8), Benjamin (6), and Grace (4). The Milaschewski family is excited to make Miami home and to begin this next chapter with the Gulliver community.
A distinguished group of donors who are leading the way in Centennial fundraising with new transformative gifts of $100,000 or more, helping to shape the next century of excellence at Gulliver.
Leila Zivkovic is a human rights attorney, business leader, and devoted mother of three. With over 20 years of global experience in human rights, justice reform, and post-conflict development, she has worked with the UN, OSCE, British Army, World Bank, and other international organizations.
Leila led war crimes prosecutions in Bosnia with the OSCE and was awarded the UN Medal for Peace by HM Queen Elizabeth II for her service with the British Army. She currently consults for the World Bank on legal frameworks in the Balkans and is a board member of OKAPI Train, a military and police security training company. As a partner at Springshare LLC, she also contributes to educational technology worldwide.
A strong supporter of immigrant rights and animal welfare, she remains active in pro bono legal work and rescue efforts. Leila is a proud Gulliver Prep parent with two children currently enrolled.
Eion Hu P ‘30 ‘30
Eion Hu grew up in North Jersey and currently resides in Miami. He graduated from DePaul High School (N.J.) in 1993, Harvard College in 1997, and Harvard Business School in 2003. Eion has spent his career in finance, joining Salomon Smith Barney in the Mergers and Acquisitions group in 1997 and TJC, a leading middle-market private equity firm, in 1999. Since then, he has helped build the culture and core values at TJC through the continuous mentorship of the firm’s younger professionals and partnerships with great companies and talented executives.
Eion is a member of TJC’s Partnership Board, Executive Committee, and Investment Committee. He serves as Head of the Executive Committee of the Friends of Harvard Football, member of the Harvard Varsity Club board of directors, and member of the Harvard Athletics Visiting Committee.
Christopher Drew P ‘31
Christopher Drew is a Senior Managing Director and Co-Head of JLL Capital Markets’ Miami office. With over 20 years of experience, he joined JLL through the acquisition of HFF, and he is primarily responsible for executing and overseeing the day-to-day operations of the Miami Debt and Equity Placement team.
Christopher specializes in arranging various forms of financing for real estate assets nationwide, including joint venture equity, preferred equity, mezzanine financing, and senior-level financing. He secures financing for all asset types, including retail, office, industrial, multifamily, cold storage, and more.
Prior to joining JLL, Christopher held senior finance and leadership positions at HFF, Cushman & Wakefield, and the New York Mets organization. He holds an MBA and a Bachelor of Business Administration from the University of Miami and serves on the board of CTO Realty Growth.
Kris Siemionow P ‘30 ‘33
Dr. Siemionow (MD, PhD) is an orthopedic surgeon by training and an entrepreneur who has founded and co-founded a number of medical companies that use advanced technology to improve clinical outcomes.
Dr. Siemionow completed a residency in orthopedic surgery at the Cleveland Clinic Foundation and a fellowship in spine surgery at Rush University Medical Center. His PhD focused on the effects of inflammation on nerve cell function. Dr. Siemionow is co-founder of Global Spine Outreach, a non-profit organization whose mission is “to save children with severe spinal deformities.”
He is co-founder of Holo Surgical Inc, a digital surgery company that has developed an artificial intelligence-based surgical guidance system that now has clinical applications. He is also co-founder of Inteneural Networks Inc, a company that uses machine learning to diagnose neurodegenerative disorders. He is also a co-founder of Kardiolytics Inc, a company that uses artificial intelligence machine learning to develop algorithms for automated analysis of cardiovascular CT images. Dr. Siemionow has authored more than 100 peer-reviewed articles, abstracts and chapters in books on surgery and basic scientific research. He holds 50 patents and patent applications that have been successfully commercialized.
Dr. Siemionow is currently a board member of Dystrogen Therapeutics, Kardiobot, Dystrogen Gene Therapeutics, and Biometrics.
Jackie Mansfield P ‘24 ‘25 ‘25
Jackie Mansfield is a founding member of Tristar Capital, a boutique real estate development and investment firm with offices in New York City and Miami. After spending several years on Wall Street in the Mortgage-Backed Securities departments of Morgan Stanley and Daiwa Securities, Ms. Mansfield partnered with David Edelstein in the late 1990s with their first acquisition of a portfolio of properties on Lincoln Road in Miami Beach.
Over the past 25 years, Tristar has developed or repositioned a variety of high-profile real estate assets including the critically acclaimed W South Beach Hotel & Residences in Miami Beach, FL and the Miracle Mile Shops on the Las Vegas Strip. In addition, Tristar has amassed a substantial portfolio of Class A trophy office buildings headquartered by large cap tech tenants including Apple, Facebook and Amazon in core urban locations in Seattle, WA, Bellevue, WA, and Silicon Valley, CA.
In addition to her investments with Tristar, Ms. Mansfield led a small investment group in the acquisition of a 100-key beachfront hotel in the historic summer enclave of Montauk, Long Island. She was also involved in buying and repositioning three boutique hotel properties in Southampton, including the popular Capri Hotel.
Ms. Mansfield serves on the Board of Directors for Breakthrough Miami and is a member of the Real Estate Advisory Board for the Herbert School of Business at the University of Miami. Ms. Mansfield has three children that are Gulliver Lifers.
Fabio Ribeiro P ‘27 ‘28
Fabio Ribeiro has led diverse teams at the dawn of the internet, helping pioneer Brazil’s iconic ISP, iG. He founded and successfully exited SOL, a business in the aviation industry, and went on to start Neptuno in 2003, a multi-strategy fund focused on technology and forward-thinking investing. In recent years, he has guided Neptuno into the venture capital space, with a vision to empower entrepreneurs at the convergence of exponential technologies.
Fabio holds a BA from FAAP, São Paulo, a Master’s degree in Economics from Bocconi University, Milan, and an MFA in Interactive Media and Game Design from the University of Miami. He currently serves on the boards of Aura Minerals and the Institute for Data Science & Computing and the School of Communications, both at the University of Miami. Fun Fact: Fabio is a helicopter and airplane pilot.
Sergio Rhein Schirato P ‘28 ‘32
Sergio Rhein Schirato has over 25 years of experience in the financial industry. In 2009, he co-founded Daemon Investments, a hedge fund with operations in the U.S. and Brazil, where he currently serves as CEO. Previously, he was a partner and director at Itaú-Unibanco based in São Paulo.
Sergio holds a Ph.D. in biosciences from the University of São Paulo, a Master’s in applied mathematics, and an MBA jointly awarded by NYU Stern, the London School of Economics, and HEC Paris. He also completed postdoctoral research at the Museum of Archaeology and Ethnology of the University of São Paulo. His academic contributions include numerous peer-reviewed publications on time series analysis and dynamical systems.
Beyond finance and academia, Sergio is an avid scuba diver actively engaged in conservation and exploration projects, and a passionate cyclist. He is also the proud father of two daughters.
Mike Komaransky P ‘26 ‘29
Mike Komaransky, father of Hugo ’26 and Luca ’29, graduated from University of Chicago in 2001. He worked as a trader and later a partner at DRW Trading in both Chicago and London, starting Cumberland, one of the world’s first cryptocurrency trading desks. He moved to Miami in 2018 and founded Grapefruit Trading, Ransky Trading and currently manages a portfolio of crypto-related investments
Vincent Signorello P ‘21
Vincent Signorello founded Scout Capital Partners in 2017 and Scout Cold Logistics in 2021. He currently serves as the Chairman and CEO of Scout Cold Logistics. Previously, Vincent was the President and CEO of Florida East Coast Industries, a wholly owned company of Fortress Investment Group. Vincent also served in executive roles at Fortress Investment Group, Barclays Capital and Lehman Brothers. Prior to his investment banking and private equity career, Vincent served as an active duty officer in the United States Army where he led reconnaissance and infantry units. Vincent supports numerous non-profit organizations involving education and veteran assistance, including serving as the previous Chairman of the Board of Trustees for Gulliver Prep. Vincent, his wife Shannon, and his two children Cole and Mason currently reside in Coconut Grove.
Transformation. Together. 2026. formally launched in May 2022, and, in October 2022, we opened the Center for Student Life at our Marian C. Krutulis PK-8 Campus. This 60,000 square foot facility was the first new building to be constructed as part of our capital campaign, and is at the heart of student life and learning. In March 2023, the Tennis Complex officially opened, marking the completion of Phase II.
With Phase III in progress, Phase IV pending fundraising, and Phase V on the horizon, we continue to make steady progress toward our campus transformation at the Upper School Campus.