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Vice President of Human Resources

Thompson Island Outward Bound
Job Title: Vice President of Human Resources
Job Type:
Job Search Ends:
January 1st, 2018
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The Oranization and It's Mission

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 researchbased 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 Thompson Island’s programs currently exceedssupply and the organization ismoving forward with plans to expand its capacity.

Position Summary

The organization functions with a year-round staff of 33 employees, which grows to 150 on-season. 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 VP of Human Resources (VPHR) will bring well-rounded experience in human resources management to ensure that staff – whether line cooks or field science educators, wedding planners or deck hands, fundraisers or administrators – all enjoy a positive, safe, and rewarding work environment, as the organization grows in its ability to attract, retain and grow the best talent, serving as an employer of choice, with a 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 navigating the challenges and opportunities inherent in a workforce of dedicated individuals working on and off an island in positions that vary significantly in responsibility and hours but not in dedication to making Thompson Island a memorable experience 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 a full-time Staffing Director and up to two other positions, report to the organization’s Executive Vice President (EVP), and serve as a member of the aforementioned Senior Management Team, which currently 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 opportunities to spend time on Thompson Island.

Essential Duties and Responsibilities 

Functional responsibilities include, but are not limited to:

  • Participating in the development of TIOBEC’s plans and programs as a strategic partner, focusing on the impact on people, and translating the organization’s strategic plans 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 and leading a Board of Trustees committee on Human Resources and Organizational Development 


This position reports to the Executive Vice President, working closely with the additional members of the Senior Management Team. The VPHR directly supervises a staff of 1-3 people, while providing direct oversight for all Hiring Managers within the organization.


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, with MBA or relevant Masters Degree preferred or significant experience equivalent to the advanced degree.
  • 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.
  • 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.
  • 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), Zenefits, PayScale and/or other employment screening and listing services
  • Knowledge of applicable federal, state and local employment, wage and hour laws and regulations.

Work Conditions 

This position reports to both 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 regulated schedule and additional flexibility during the “off season.” 

Phyisical Requirements 

As with all positions reporting for work on Thompson Island, the VPHR will be expected to participate in those activities expected of all staff, to include: loading and unloading cargo from ferry on both trips to and from the island; serving as an ambassador, equipped to share history and mission with all island guests, while touring them 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.

Compensation 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 regularly 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

This search is managed by consultant Carolyn O’Brien. 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 to TIOBEC_HR@carolynobrien.org. All applications will be acknowledged, and candidates will be contacted only if Thompson Island determines a need for additional information. 

133 Federal Street, Suite 802 | Boston, MA 02110
Phone: 617.426.2606 | Fax: 617.426.2849
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