Executive Director, SkillWorks

Department: Programs  

Reports To: Vice President for Programs  

FLSA Classification: Exempt  

FTE: 1    Supervises: 1 Senior Program Officer 


Skillworks Logo

SkillWorks is a nationally recognized workforce development intermediary and funder collaborative that has invested over $30 million over more than 15 years in innovative workforce development strategies. Launched by a group of public and private funders in 2003, SkillWorks has helped more than 7,000 individuals obtain skills training with thousands entering the workforce or receiving raises and promotions. SkillWorks has completed three five-year phases of work, and is currently operating under a four year strategic plan that launched in 2018 and will run through 2021.  

SkillWorks is an initiative that is governed by the funder collaborative, or Funders Group, which is comprised of The Boston Foundation, City of Boston and other private, corporate and philanthropic supporters. SkillWorks sits within the Jobs and Economic Development impact area within the Program Department at the Boston Foundation, leveraging the considerable capacity of the Foundation in finance, operations, public policy and communications and grants management in a wide range of areas that connect to workforce development. The Boston Foundation and the Funders Group are also discussing the best way to integrate the workforce development strategy and investments across the SkillWorks and TBF grantmaking portfolios.  

In 2016, in partnership with The Boston Foundation, SkillWorks launched a new effort called PROJECT CATAPULT. Project Catapult is testing a new model that invests in the exponential growth of Greater Boston’s most effective, market-driven training and education strategies by driving significant and flexible resources toward organizational capacity, development of networks of workforce and education providers, and engaging employers as true partners in shaping scalable workforce solutions. 

Vision and Strategies  

SkillWorks’ mission is to bring together philanthropy, government, community organizations and employers to address the twin goals of 1) helping low income individuals attain family supporting jobs; and 2) helping businesses find, retain and advance skilled workers. SkillWorks’ vision is to help to make Boston a place where every resident has an opportunity to thrive by making a good living and where employers have access to a diverse, well-trained, and qualified talent pool. To accomplish its goals, SkillWorks’ key strategies and investment areas are: 1) Industry Consortia, 2) Workforce Partnerships, 3) Leadership and Community Building, 4) Public Policy and Practice, and 5) Work Readiness and Contextualized Work Experience  

Looking Ahead  

This is an exciting time for SkillWorks. Through its skilled and committed Funders Group, SkillWorks is focusing on expanding its reach, building on over a decade of success to achieve lasting systems change in workforce development. The next Executive Director will share the passion and commitment to helping low-income individuals attain family-supporting employment and to helping businesses in the greater Boston region through accessing a skilled talent pipeline. The Executive Director will embrace innovation, collaboration and partnership in building ownership and voice among funders, partners, service providers, industry and government in designing and executing next generation workforce development models and strategies.  

In this current iteration of SkillWorks, the funders are balancing our commitment to what has proven valuable over the past 15 years with using what we have learned to enhance and shift our strategies to create broader impact and systems change. SkillWorks and the Boston Foundation launched Project Catapult to take advantage of the generational opportunity of a tight labor market to develop, pilot and evaluate next generation workforce strategies in partnership with funders, providers and employers. The learning that we do through Project Catapult will inform the next phase of the SkillWorks funders collaborative vision and strategy.  

The new Executive Director will have the opportunity to lead the funders collaborative through a strategic planning process that builds on our success and learning and grows our coalition and collective impact. SkillWorks is a national leader in building and sustaining a funder collaborative that is grounded in its mission, forward looking in its strategies and aspirational in its goals.  

Learn more about SkillWorks at   


Reporting to the SkillWorks Funders Group and the Vice President for Programs at the Boston Foundation, the Executive Director is responsible for the overall success of workforce development strategies and investments made through SkillWorks and Project Catapult. The Executive Director is charged with building on SkillWorks’ track record, realizing the initiative’s vision, expanding and deepening the engagement of funders and partners, maintaining continued financial stability and achieving excellent outcomes for participants and businesses as well as workforce systems and policy changes aligned with initiative goals. The Funders Group and TBF are seeking a leader who is the face and voice of SkillWorks and can shape and communicate the strategy in a clear, concise and compelling way. The next Executive Director will be a systems thinker and movement builder and will effectively engage and grow the funders collaborative.  

The Executive Director will lead and manage the organization’s strategic and operational growth, including staffing, resource and budget planning, fundraising, and will steward relationships with SkillWorks’ funders, business and community partners. S/he will also provide forward-thinking leadership, and manage in an open, collaborative environment. S/he will have the ability to manage multiple stakeholders and streams of work and navigate the public policy/advocacy and practitioner worlds. The Executive Director will value and engage the diverse voices of the community, believe deeply in the transformative power of workforce development. S/he will have the skills and knowledge to engage local employers and enhance their level of commitment to partnering and supporting community-based workforce development efforts as a business imperative.  

The Executive Director of SkillWorks is an employee of the Boston Foundation in the Program Department. The Boston Foundation is an equal opportunity employer, and provides its employees with a rich benefit package.  

Essential Functions 

  • Staffing the Funders Group to shape and execute a compelling workforce strategy. The Executive Director will be responsible for communication and close collaboration with the SkillWorks Funders Group, guiding and supporting them in meeting the initiative’s strategic goals and working with them to shape an innovative, inspiring and aspirational vision and plan for next generation workforce development strategies and models. S/he will lead a collaborative process with the Funders Group, staffing and executing decisions effectively and ensuring that the Funders Group is informed of critical developments in a timely and effective manner. S/he will work to deepen the engagement and commitment of funders and expand the number of funders engaged.  
  • Working with Senior Program Officer to conduct grant making and grants management. The Executive Director will be responsible for soliciting, selecting and managing all grants awarded by the initiative. S/he will communicate regularly with grantees, analyze grantee progress, provide support to help grantees achieve their goals, and ensure that grantee work plans and goals are consistent with SkillWorks’ and TBF’s goals.  
  • Engaging local employers to understand their talent needs and in shaping workforce development strategies and partnering with and supporting community-based workforce development efforts. The Executive Director will have a sophisticated understanding of the talent needs of local employers and the skills to communicate the value of community-based workforce providers in recruiting, developing and advancing talent.  
  • Fundraising. The Executive Director will be responsible for developing a fundraising plan for future years, bringing additional funders into the Funders Group and deepening relationships with existing funders. The Executive Director will partner with public and private funders and negotiate work plans that support the SkillWorks initiative and will assure that each funding source receives reports on program results and finances in accordance with reporting requirements.  
  • Measuring impact. The Executive Director will be responsible for overseeing evaluation efforts, including contracting with any external evaluators, designing data collection procedures and templates for grantees, facilitating the regular collection and reporting of participant and business impacts, and assisting grantees and subcontractors in outcomes measurement that assists the funders in assessing the impact of the initiative.  
  • Building a learning community. The Executive Director will ensure that learning, innovation and collaborative action among grantees, funders and other stakeholders are maximized, overseeing and developing such efforts as capacity building workshops, peer learning groups, tools and publications based on SkillWorks’ learning and evaluation, presentations and webinars as appropriate.  
  • Serving as SkillWorks’ chief spokesperson and engaging a wide range of partners, stakeholders and constituencies. The Executive Director will serve as the lead ambassador for the SkillWorks initiative, internally and externally, communicating its strategy in a clear, concise and compelling way. S/he will, with the support of the Funders Group and the Boston Foundation, represent SkillWorks at local, regional and national meetings, participate in boards and collaboratives that are aligned with SkillWorks’ interests and goals, and lead public policy and advocacy efforts to insure the success and growth of SkillWorks’ strategies.  
  • Overseeing consultants and contractors: The Executive Director will be responsible for regular communications with all consultants and contractors retained by the Funders Group or the Boston Foundation. The Executive Director will negotiate the terms of contracts and contract renewals, coordinate work plans and facilitate information sharing as relevant to develop among them a core expertise and commitment to maximizing the systems change opportunities of the initiative. Overseeing staff. The Executive Director will actively manage and develop current staff and hire and oversee any administrative or program staff and ensure that the organization is effectively structured and managed.  


  • Demonstrated leadership and relationship building skills, including the ability to manage a Board of Directors, partners and stakeholder groups and inspire and project a vision for the initiative,  
  • Proven ability to effectively communicate complex ideas and initiatives to multiple and varied audiences, including philanthropy, policymakers, local employers, providers and community leaders, in a way that leads to buy-in and collective action,  
  • Knowledge of workforce development systems, financing, and program design and the ability to be a thought leader in developing innovative workforce development models and policies that lead to structural change,  
  • Familiarity with grant making, grants management, evaluation and performance management,  
  • Project management skills and experience with complex, multi-component programs, organizations, or initiatives, including a track record of change management,  
  • Seven to ten years of relevant work experience with a proven track record of management success,  
  • Bachelor’s degree required; Master’s degree in related field (e.g. MBA, MPP, Public Administration, or Social Work,) from an accredited university preferred,  
  • Strong financial management skills, including budgeting and cash flow management,  
  • Experience with fundraising and stewardship, including grant writing and proposal development,  
  • Experience with public policy advocacy and communications.  

 Personal Characteristics

  • Mature interpersonal style, ability to interact well with a diverse range of people and be inclusive, flexible, creative, energetic, and fair minded,  
  • Commitment to equitable and thriving communities and passion for the power of workforce development to transform individuals, families, and communities,  
  • Ability to make decisions about how to manage and organize own workload,  
  • Ability to manage and work as a member of a small team,  
  • Ability to work successfully under the pressure of tight deadlines and with limited resources,  
  • Participative and collaborative work style; ability to give and receive feedback,  
  • Accepts responsibility and takes charge of results.   

The content is intended to describe the general nature and level of work being performed by persons assigned to this job. It is not intended to constitute an exhaustive list of all responsibilities and duties required.  

External and internal applicants, as well as position incumbents, who are or become disabled as defined under the Americans with Disabilities Act or applicable state law, must be able to perform the essential functions of the job (including those listed above) either with or without reasonable accommodation. Reasonable accommodation, if any, will be determined by management in consultation with the employee on a case-by-case basis.  

This job description is intended to be general and may be revised from time to time. At management’s discretion, the employee may be assigned different or additional duties from time to time.