Executive Director

About Prisoner’s Legal Services of Massachusetts 

Our mission is to challenge the carceral system through litigation, advocacy, client counseling, partnership with impacted individuals and communities, and outreach to policymakers and the public in order to promote the human rights of incarcerated persons and end harmful confinement.

Prisoners’ Legal Services of Massachusetts (PLS), is a nonprofit legal services office founded in 1972 that provides civil legal assistance to the thousands of individuals incarcerated in Massachusetts state prisons (Department of Correction facilities) and county jails and houses of correction.

With a staff made up of attorneys, paralegals and support personnel, and a Board of Directors consisting of attorneys, community leaders, medical professionals, researchers, clients, and former clients, we engage in individual and systemic impact litigation; provide direct administrative advocacy regarding prison conditions and parole; initiate and support legislation to promote the civil and human rights of incarcerated individuals and their families; work to eliminate institutional racism and its impact on Black and Brown incarcerated individuals in the day-to-day operations of Massachusetts prisons and jails; and work with media and community organizations to educate the public about the criminal legal system.

While PLS responds to requests for advice and guidance from prisoners and their families on many issues, its work is focused on five key priorities critical to our clients:

• Health Care
• Staff Assaults
• Conditions of Confinement
• Solitary Confinement
• Racial Equity in Corrections

As an anti-racist organization, PLS approaches all of these priority areas through a racial equity lens. More information is available at PLSMA.org.

The Opportunity

This is an extraordinary opportunity for a seasoned, people-centered, and collaborative leader who is a bridge-builder with deep knowledge of diversity, equity, inclusion, and belonging best practices. The Executive Director will lead a team of 33 staff members with 8 direct reports and is responsible for the programmatic performance, financial strength, and administrative functioning of the organization. The Executive Director will engage, motivate, and inspire members of the staff and Board and a broad range of other supporters and constituents.

Deeply committed to advancing anti-racism and challenging the carceral system, the Executive Director will demonstrate a fervent dedication to addressing the needs of incarcerated individuals and confronting systemic issues through litigation, advocacy, and client counseling. Leading with integrity and authenticity, the Executive Director will have a proven track record in fostering partnerships with impacted communities, engaging with policymakers, and raising public awareness and a will have a history of leadership in policy work with substantive expertise in legal issues affecting prisoners and their families.

 The Executive Director’s responsibilities include, but are not limited to, the following: 

Organizational Leadership and Management

• Engage the staff, Board, and other key constituents in articulating a shared vision and direction for PLS internally and externally, ensuring that a range of voices are considered and reflected in that vision.
• Provide day to day leadership and management for the organization, ensuring that the organizational structure, systems, and processes are effective, roles and responsibilities are clear, and team members have the support and resources required to be successful.
• Support with major or complex litigation to address systemic issues that affect PLS’s clients.
• Provide compassionate leadership and maintain a participatory and collaborative culture that attracts, retains, and motivates a diverse and talented staff, and a management approach rooted in listening, learning, and gaining collective buy-in.
• Deepen diversity, equity, inclusion, belonging, and anti-racism across all parts of the organization to foster an inclusive, equity-forward culture.

Financial and Operational Oversight

• Develop and expand PLS’s financial resources and ensure rigorous and consistent financial and administrative oversight, including tax filings, annual audit, budgeting, forecasting, and financial reporting to enhance and maintain the long-term financial and institutional security of the organization.
• Deploy nonprofit best practices to ensure that responsible policies and risk management procedures are in place to keep the organization viable and sustainable.
• Work closely with the Board to develop and manage the annual budget.
• Ensure compliance with all legal, regulatory, and ethical standards and practices.

Fundraising and Resource Development 

• Work closely with the Development Director and the Board to guide and participate in the organization’s fundraising efforts with a current target of $245K, including grant writing and reporting and legislative and private fundraising.
• Secure new sources of funding and diversify existing revenue streams to strengthen PLS’ financial position.
• Maintain, develop, and enhance positive relationships with key current funders while identifying, cultivating, and securing new donors.
• Serve as a persuasive and inspirational fundraiser for PLS, working in collaboration with the Development team and Board to set, pursue, and secure ambitious and sustainable fundraising goals.

External Relations   

• Represent PLS before the legislature, courts, and other government entities.
• Drive visibility and recognition through strategic oversight of organizational communications.
• Assess opportunities to represent PLS in public forums, leverage internal expertise and delegate strategic opportunities for staff for public speaking and media engagement that amplify PLS’ presence and profile.
• Work cooperatively with other institutions and organizations to achieve shared goals relating to criminal legal system reform.

Board Relations

• Communicate regularly with the Board of Directors to ensure that they are appropriately and consistently engaged and informed.
• Provide regular updates to the board on all key organizational initiatives.
• With team support, prepare for productive board meetings, including developing agendas in consultation with the Board Chair, creating supporting materials, and managing logistics.
• Support the Board as needed to ensure best practices around governance and ethics.

Candidate Profile:

We recognize that there is a spectrum of lived and professional experience that will set candidates up for success in this role. While no one candidate will have every experience outlined in the position description, ideal candidates will offer a track record of demonstrable success and strength in the areas of responsibilities listed above as well as:

• At least 10 years of experience as an attorney and at least five years of demonstrated success as a manager in the nonprofit social justice community. Comparable experience in related fields demonstrating a similar level of understanding and skill, including extensive experience in legal advocacy and litigation, policy analysis, compliance, or other fields closely related to the legal profession, can be substituted for a JD.
• Experience leading fundraising efforts that result in measurable growth in annual revenue and comfort and familiarity not only overseeing revenue, but also making asks and closing deals.
• Experience dealing with diverse audiences (e.g., legislators, prison officials, community partners) and framing initiatives accordingly.
• The ability to manage difficult conversations and divisive topics with strong mediation skills, keen emotional intelligence, firm decision making, and transparency.
• Experience working with marginalized communities with a clear goal of centering the clients and valuing the wisdom of lived experience.
• Bilingual skills in Spanish, American Sign Language, or other language common in the prison system preferred. 

Compensation & Benefits

This is a full-time exempt position with a salary range of $150-175K. PLS provides a generous benefits package, including 27 vacation days, 17 sick/mental health days, and 100% paid health, dental, and vision insurance plans. Currently this is a hybrid role with some in-office time in Boston expected. In addition to in-office time, the Executive Director can expect to have regular in-state travel for prison and jail visits, legislative work, and meetings with other offices and organizations.

Contact

Koya Partners l Diversified Search Group has been exclusively retained for this engagement, which is being led by Molly Brennan, Sarah Avendaño, and Glenn Wiggins. Submit a compelling cover letter and resume by filling out our Talent Profile. All inquiries are strictly confidential.

Koya Partners l Diversified Search Group is committed to providing reasonable accommodation to individuals living with disabilities. If you are a qualified individual living with a disability and need assistance expressing interest online, please email [email protected]. If you are selected for an interview, you will receive additional information regarding how to request an accommodation for the interview process.

Prisoners’ Legal Services of Massachusetts is an equal opportunity employer and strongly encourages applications from people of color, persons with disabilities, women, and LGBTQ+ applicants.