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Vice President for Human Resources

Thompson Island Outward Bound Education Center
Job Title: Vice President for Human Resources
Job Type:
Job Search Ends:
January 15th, 2020
Organization's Website:

“The work of Thompson Island shows how important learning in the real world is for young people.” - Boston Globe Editorial

At Thompson Island Outward Bound we believe every kid can discover the freedom of possibility, as students move from "I can't” or “I'm not" to "I can." I can navigate turbulent waters. I can be part of a team. I can lead. I can reach the top. I can solve that problem. I can make a difference for others. I can go to college. I can feel smart. I am smart. "I can, I will, I am."

Through our partnership with Boston’s public schools, each year thousands of students board the Thompson Island Outward Bound ferry to discover who they are and all they can become, on an island classroom that spans 204 acres of salt marshes, woods, campsites, labs, dormitories, and dozens of challenge structures.

In order to reduce the achievement and opportunity gaps facing Boston middle schoolers, our research- based curriculum features hands-on field science infused with Outward Bound’s unique approach to character development. Our multi-year education programs are provided at no cost to schools or students, funded by a combination of philanthropy and the island’s events business.

A local and national treasure, Thompson Island Outward Bound Education Center is located in the Boston Harbor Islands National Park, just one mile from downtown Boston. Since 1833, the island has functioned as a non-profit, expanding education and life opportunities for Boston youth. Thompson Island Outward Bound Education Center is part of the national network of 11 Outward Bound USA sites, the mission for which is Changing Lives Through Challenge and Discovery. Outward Bound is present in 33 countries.

Demand for TIOBEC’s programs currently exceeds supply and the organization has adopted an ambitious plan to scale its size and impact in the next few years.


The new Vice President of Human Resources (VPHR) will join TIOBEC at a time of exciting change and growth, not just in budget and staff size, but also in the organization’s vision for serving Boston Public School middle school students. As both a strategic thinker and a hands-on implementer, the VPHR will seek opportunities to make TIOBEC an excellent place to work, whether one is commuting to the island daily to teach field science or working in the Seaport office suite, producing marketing materials. As TIOBEC grows to serve 15% of BPS middle schoolers, the successful VPHR will skillfully develop and integrate authentic approaches to Diversity, Equity, and Inclusion to build an organizational culture that matches TIOBEC’s values and maintains its collegial, students-first experience.

Navigating the complexities of an organization that functions with a year-round staff of 50 employees, but grows to 150 on-season, is among the position’s challenges. The many and diverse programs on Thompson Island, coupled with TIOBEC’s mission, result in a varied and complex set of responsibilities for the Human Resources function. The VPHR will bring well-rounded experience in human resources management to ensure that staff – whether line cooks or educators, wedding planners or deck hands, fundraisers or administrators – all enjoy a positive, safe, and rewarding work environment. TIOBEC seeks a leader to grow its ability to attract, retain and support the best talent; serve as an employer of choice, and evidence its deep commitment to diversity, equity and inclusion. This includes overseeing policies and procedures and ensuring an excellent and affordable benefits package and competitive salary structure.

The position serves as a crucial member of the Senior Management Team and requires enthusiasm for and experience in supporting a team that consists of not only professionals in an office environment, but positions that vary significantly in responsibility, hours, and off- or on-island location, but not in dedication to making the Thompson Island Outward Bound experience memorable in students’ lives and the lives of all the island’s 20,000+ annual visitors.

As a human resources generalist and expert, the VPHR will supervise two full-time direct staff members, report to the organization’s Executive Vice President (EVP), and serve as a member of the aforementioned Senior Management Team, which includes the VP of Development, the island’s General Manager, the EVP, the CFO, the VP of Education, and the CEO. This is a full-time position located in Boston’s Seaport District with regular time spent on Thompson Island.


Functional responsibilities include, but are not limited to:

  • Contributing to the development of TIOBEC’s plans and programs as a strategic partner, focusing on the people and translating the organization’s goals to scale its impact and its commitment to Diversity, Equity, and Inclusion into HR strategic plans and practices.

  • Advising senior management on the impact of long-range planning and new programs/strategies and regulatory action as those items affect the attraction, motivation, development and retention of employees.

  • Developing, maintaining and communicating organizational personnel policies and procedures, while ensuring managers’ training about the policies and serving as a coach to them in working with their staff to ensure organization-wide compliance and consistency.

  • Overseeing recruitment, hiring, orientation and on-boarding of all employees.

  • Overseeing administration of all employee benefit plans, including negotiating, through a broker, with vendors for coverage on health, dental, life, long-term disability, employee assistance and 401(k) retirement plans. The VPHR will ensure that TIOBEC continues to offer competitive benefits within the organization’s financial resources.

  • Managing professional development to both ensure managers are trained in all relevant subjects (including hiring and terminations, performance management, EEO policies including sexual harassment, and safety) and that all employees have opportunities for growing skills and knowledge in their fields.

  • Supporting, coaching, and facilitating the positive resolution of employee relations issues in a manner that contributes to TIOBEC’s employee-centered workplace and high-performance culture.

  • Tracking legal requirements and government reporting regulations affecting human resources functions, and ensuring TIOBEC’s policies, procedures, and reporting are in compliance.

  • Developing a Board of Trustees Human Resources committee.


Successful candidates will share TIOBEC’s commitment to a diverse and dynamic community of educators and learners, dedicated to shaping a better future for Boston students. Much in the way that students on Thompson Island must apply resilience and humor to the unpredictability of learning on an island in the middle of Boston Harbor, so must the leader of TIOBEC’s human resources department. Dozens of team members work unusual schedules and seasonal positions. Some staff work in offices but many work outdoors in New England’s weather. Many commute to work each day on TIOBEC’s ferry. Some work with youth; some work with adults.

Strong candidates will have demonstrated success in the functional responsibilities described above, as well as:

  • BA/BS degree required. Masters Degree preferred.

  • 10-plus years of progressively responsible HR management experience, including demonstrated experience in a senior position managing the personnel functions of a complex organization.

  • PHR or SPHR or SHRM certification.

  • Experience both building and working in a Diverse, Equitable, and Inclusive workforce. Ideal candidate will have experience developing and implementing DEI strategies.

  • Experience conceptualizing, implementing and evaluating organization-wide strategic initiatives.

  • Ability to juggle multiple short-term and long-term needs, responding to challenging employee relations issues while planning for new professional development strategies in the course of a day.

  • Ideal candidate will have experience in organizations (for-profit or non-profit) that have moved through a significant growth phase in number of employees and size of budget.

  • Excellent communication skills, both written and oral, and demonstrated proficiency with ADP Payroll Systems (Workforce Now Payroll, Time and Attendance, and Human Capital Management Suite), Bamboo, PayScale and/or other employment screening and listing services.

  • Knowledge of applicable federal, state and local employment, wage and hour laws and regulations.


This position works in both the Mainland and Island offices. Hours are more variable during the height of the season, and will include occasional nights and weekends, while allowing for a more regular schedule and additional flexibility during the “off season.”


As with all positions reporting for work on Thompson Island, the VPHR will be expected to participate, as able, in a range of assistance: serving as an ambassador for the Island’s work, occasionally sharing history and mission while touring guests around the island; walking distances of up to a mile to attend to employee, client or operational needs, as they arise, at various locations around the island; and loading and unloading light cargo from the ferry on both trips to and from the island.


Competitive salary, commensurate with experience. Employer sponsored health insurance with the option to select between comprehensive, valuable plans. Vision, dental plan and life insurance. 401(k) retirement plan with competitive match. Generous paid time off including vacation, federal holidays, personal and sick days. Flexible scheduling, pursuant to position. Eligibility for annual raises or bonuses awarded based on achievement of organizational goals and individual 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.


This search is managed by Carolyn O’Brien Consulting, LLC. No phone calls please, but referrals are welcome. Email a resume titled with your last name and initial and resume (e.g. COSTA_L_RESUME) and a detailed cover letter with the same naming convention to TIOBEC@carolynobrien.org. All applications will be acknowledged, and candidates will be contacted only if Thompson Island Outward Bound determines a need for additional information.

Thompson Island Outward Bound Education Center is an equal opportunity employer and actively seeks a diverse staff group, 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.

133 Federal Street, Suite 802 | Boston, MA 02110
Phone: 617.426.2606
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