Vice President of Education
Thompson Island Outward Bound Education Center
February 17, 2016
Thompson Island Outward Bound Education Center in Boston, Massachusetts, seeks an
adventurous, experienced educational leader to oversee and advance the innovative programs
that make Thompson Island “Boston’s Island Classroom.” Reporting directly to the President
and CEO, the Vice President of Education will oversee the staff who design, manage, and deliver
TIOBEC’s signature next-generation science learning programs for Boston Public Schools
students; emerging professional development work with teachers and principals; and established,
fee-for-service adventure-based programs for youth-serving organizations throughout the
region. This is an exciting opportunity for someone who has a deep commitment to closing the
achievement gap by extending environmental and experiential learning across Boston and
beyond as well as a genuine enthusiasm for Thompson Island’s unique resources.
Introduction to the organization and to the position
Serving over 5,000 young people annually, Thompson Island Outward Bound Education Center,
Inc. is an independent Massachusetts non-profit based in Boston and a chartered member of the
Outward Bound USA network. The organization owns and operates one of the largest, most
accessible and ecologically diverse islands in the Boston Harbor Islands National Recreation
Area. The island has been home to ground-breaking learning-by-doing educational opportunities
for Boston youth since 1833.
With 204 acres of undeveloped property located just one mile from downtown Boston, the island
features mature forests, meadows, freshwater and marine wetlands, salt marshes and a variety of
important geological features. Thompson Island also has a formal school campus complete with
dormitories, dining hall, classrooms, lab space, library, auditoriums, gymnasium, four challenge
courses, and a 60-foot climbing tower – a unique educational resource ideally suited to be
“Boston’s Island Classroom.”
To augment the impact of philanthropic investments, Thompson Island manages a conference
center and unique event and wedding facilities that allow the community to enjoy the island
while supporting its youth programming.
Our mission is to change lives through challenge and discovery. We provide expanded learning
programs that close opportunity and achievement gaps for Boston’s low income youth through
hands-on learning which fosters academic success, perseverance, self-discipline, leadership and
compassion.
We operate two primary initiatives in this work – Year Round Connections (YRC) and
Discovery. Inspired by best thinking in STEM education and guided by rigorous evaluations,
YRC combines school year activities with summer programming as a basis for deep, year-round
learning partnerships that engage students in carefully sequenced, progressively challenging
work from 5th through 8th grade. Offered free to Boston public schools (district and charter),
YRC’s “next generation science learning” integrates best practices in field science investigations
with Outward Bound’s world-renowned process for promoting social-emotional learning. A
growing Professional Development initiative engages teachers and principals from our YRC
schools, and eventually to a broader cadre of schools, in order to expand the reach and impact of
the island.
Likewise, our traditional adventure-based program – Discovery – is gaining relevance as
perseverance, self-discipline, teamwork and leadership emerge as critical factors in the research
on academic attainment. We serve thousands of students through these fee-based programs and
seek to become a more effective partner to our clients and to other youth-serving organizations
that utilize these programs.
The Vice President of Education (VP) reports directly to the President and CEO and is a key
member of the seven-person senior management team. The VP will work closely with the
island’s Executive Vice President, who provides support and coordination across all of the
organization’s departments.
The VP oversees all staff who design, manage and deliver these YRC and Discovery programs,
as well as our adult OB courses, a modest youth summer jobs program, and additional initiatives.
In sum, the VP of Education will lead a vibrant team of experiential education and STEM
experts in building the next chapter in Thompson Island’s historic commitment to innovative
educational opportunities for Boston youth.
Vice President of Education – Responsibilities
The Thompson Island Vice President of Education will lead a team of six direct reports,
additional full-time staff, and several dozen seasonal staff. Responsibilities include:
 Align the work on the island with best thinking and best practices in the field of expanded
learning, especially STEM education. Where applicable, ensure our work supports
Massachusetts Curriculum Frameworks as well as emerging standards for socialemotional learning.
 Manage the budget and the work of the education department, establishing clear goals
and expectations for the team and its members, providing regular guidance and
supervision and ensuring efficient communication and collaboration across programs.
Coordinate planning and implementation with Thompson Island’s ferry, food and
facilities operations in partnership with the Chief Operating Officer.
 Shape deep, long-term partnerships with schools by collaborating with principals,
teachers, families, district officials, curriculum specialists and other community partners
to optimize the value of our programs and our campus in their communities.
 Ensure that the organization can optimize the value of its fee-for-service educational
programs.
 Enhance the rigor of our instructional practices by implementing third party evaluation
that allows us to benchmark our performance against national standards and drives
continuous improvement in execution of our programs.
 Collaborate with the Development Department to inform and engage funders about our
work, our methods and our outcomes, including stewardship of donors and tracking and
reporting on activities and outcomes.
 Work in partnership with district officials, school leaders and teachers to further craft and
then implement the Professional Development initiative for educators within the school
system, so that island experiences are used to enhance school-based learning and the
island’s experiential learning methods are adopted back in the school community. Grow
this initiative to serve principals and teachers beyond Boston, harnessing the
organization’s potential to serve the field of education reform.
 Work collaboratively with other members of the senior management team to manage the
business of delivering programs alongside the island’s hospitality business in a
disciplined and harmonious fashion.
 Serve as thought partner to the CEO in defining the evolution of our programs and
partnerships so as to be more effective in closing achievement and opportunity gaps.
Requirements:
The successful Vice President of Education will bring demonstrated experience addressing
current challenges in urban education; a well-honed, effective, collaborative management style;
and a pair of sturdy, island-worthy boots. A sense of humor is a must when overseeing programs
that safely serve scores of individuals from all walks of life, each of whom must take a ferry in
order to participate.
The successful candidate will demonstrate most if not all of the following:
• Substantive knowledge of current issues in urban education, from the perspective of an
educator or thought leader, as well as the critical role expanded learning opportunities play in
improving student outcomes
• Clear understanding and commitment to data driven decision making, and an understanding of
current local, state, and national methods for measuring student outcomes
• Experience within or in partnership with an urban public school system, ideally the Boston
Public Schools
• Exceptional staff management skills, with a history of developing new leaders and strong,
effective teams
• Passion for the out-of-doors and the resilience to offer hands-on leadership for programs that
occur on an island in Boston Harbor amidst the vicissitudes of New England weather
• Ease and experience in developing program budgets, supporting fundraising efforts, and
communicating both program needs and mission relevance to all audiences
• Demonstrated success managing and developing institutional and community partnerships
• Prior experience in developing, delivering, designing or evaluating expanded learning
curriculum, preferably with a STEM focus
• Passion for making a difference for Boston’s youth
• A Bachelor’s Degree required; advanced degree in a relevant field preferred
Salary and Benefits
Competitive salary, commensurate with experience. Employer sponsored health insurance with
the option to select between two comprehensive, valuable plans. Premier dental plan. 401(k)
retirement plan with competitive match. Generous paid time off including vacation, holidays,
personal days and sick leave. Flexible scheduling, pursuant to position. Eligibility for annual
bonuses awarded based on achievement of organizational goals and performance. Work that
engages a diverse and dynamic community of educators and learners, with the shared vision of
shaping a better future for Boston students. A quality work life in Boston’s vibrant Seaport
district as well as the natural wonders and positive impacts of Thompson Island.
To Apply
Submit: 1) a thoughtful cover letter; 2) a resume demonstrating the above qualities and
qualifications; and 3) a relevant writing sample of no more than 1-2 pages, such as an excerpt
from an education memo, proposal, evaluation report or concept paper. Please submit your
application as a PDF using the naming convention: Last_Name_Resume,
Last_Name_Cover_Letter, Last_Name_Writing_Sample. This search is being conducted by
Carolyn O’Brien, Carolyn O’Brien Consulting. Submit materials, questions, or nominations to:
VPEsearch@thompsonisland.org. No phone calls please.
Thompson Island Outward Bound Education Center is an equal opportunity employer and
actively seeks a diverse staff reflective of the communities it serves. All qualified applicants will
receive consideration for employment without regard to race, color, religion, sex, sexual
orientation, gender identity, national origin, disability status, protected veteran status, or any
other characteristic protected by law.