Director of Programs, On The Rise

On The Rise Seeks Director of Programs

About On The Rise

On The Rise, Inc. (OTR) is a dynamic Cambridge, MA-based non-profit founded in 1995 that serves women, trans, and non-binary people currently/formerly experiencing homelessness throughout the region through two interconnected programs. The Safe Haven day program provides a space where participants can meet some of their tangible needs, such as taking a shower, receiving their mail, or doing laundry, as well as meet one-on-one with advocates (staff members) to work on longer-term goals. The Keep The Keys program supports participants as they transition into stable housing and the opportunities and challenges that it presents. OTR’s innovative approach supports participants’ initiative and core strengths to help them find safety and discover new possibilities. OTR is committed to social justice, dismantling oppression, and striving to be an anti-racist organization.

The core of On The Rise’s work is building authentic, long-term relationships with program participants. Through these relationships, OTR fosters the trust and belonging that are foundational to people’s feelings of empowerment and safety in community. Program participants display enormous strength and ingenuity in coping with challenges such as homelessness, domestic violence, physical and mental health issues, the after-effects of childhood abuse, involvement in the legal system, systemic oppression, and intergenerational trauma. OTR works to meet people where they are and follows their self-determined visions of success as they navigate structural barriers and challenges. OTR strives to create a low-threshold environment where people can bring their whole selves, while also holding each individual accountable to the community.

The On The Rise team includes 17 staff members and 2 interns and is supported by a 10-member Board of Directors. The organization’s annual budget is ~2.4M. OTR provides innovative, evidence-based, and effective services to over 450 women and gender expansive participants annually. The organization has helped over 600 people secure housing, and 92% are still housed today. Please visit OTR’s website to learn more about its history, team, values, and impact.

The Director of Programs Opportunity

On The Rise is at a pivotal moment in the organization’s 30+ year history. Program participants face increased discrimination, reduced protections, and cuts to social supports, driving a significant increase in demand for OTR’s services. As such, the organization recently took a deliberate, collaborative approach to revising major elements of its programming, driven by staff and participant feedback. These changes, including bringing back Saturday hours in the Safe Haven and adjusting drop-in hours, allow OTR to focus more on staff well-being while enabling the team to deepen the individualized services they provide to participants on site and in the community. OTR is also looking to the future – the organization is working to codify and document its program model and approach in preparation for future growth with quality.

The Director of Programs will join a strong, collaborative, and talented team in a role that will shape the future of On The Rise’s programs and impact. The Director will directly manage a team of 6 Community Advocates who work across the organization’s two core programs and will serve on the organizational leadership team alongside the Executive Director, the Director of Development & Communications, and the Director of Finance & Operations. The Director will also work closely with the Senior Training and Practice Specialist/Clinical Supervisor to provide holistic clinical and supervisory support to Advocates.

The core responsibilities of the Director of Programs include:

• • Oversee program strategy and implementation
  • Ensure program quality and impact measurement
  • Provide direct supervision to Advocates
  • Cultivate and manage external partnerships to enhance programs
  • Continue to build an inclusive, collaborative, high-trust team and organizational culture
  • Serve as the program representative and voice on the senior management team
  • Engage in direct service work
  • As a member of the senior management team, play a major role in advancing broad organizational goals: e.g., determining strategic direction, supporting fundraising and communications, developing organizational policy, managing finances and risk and protecting assets, and maintaining/enhancing On The Rise’s reputation and visibility

Profile of the Ideal Candidate

This is a pivotal leadership role for someone energized by the intersection of people, programs, and systems—and who understands that excellent participant support comes through the efforts of a well-supported staff team. The right person will be a seasoned, relational leader with meaningful experience in direct service and supervision, ideally in organizations working with people experiencing homelessness, complex trauma, mental health challenges, and/or other intersecting needs. They will lead with trust, humility, and a deep commitment to equity, self-determination, dignity, and participant voice, while also setting clear expectations and supporting staff through the emotional intensity of the work.

This role requires someone who can move fluidly between the immediate and the strategic: stepping into a difficult situation when needed, coaching and developing staff, and building the systems, training, and infrastructure that make strong programs sustainable and ready for growth. They will be a transparent communicator who actively seeks frontline perspectives and brings them into leadership discussions, navigates disagreement and ambiguity, and explains the “why” behind decisions. The work is complex, fast-moving, and not always predictable, so success will require sound judgment, flexibility, a sense of humor, and comfort operating in a dynamic environment.

With this in mind, On The Rise will most likely be interested in candidates who can demonstrate a majority of the qualifications, skills, and experiences listed below.

Desired Credentials

• • Commitment to OTR’s mission and values: relationships, self-determination, wellbeing, safety in community, inclusion and diversity, and anti-racism and anti-oppression
  • Dedication to OTR’s tenets of harm reduction, trauma inclusion, relational-cultural theory, strength-based de-centered practice, a wellbeing approach, and anti-oppression frameworks + familiarity with restorative practices
  • Significant supervisory experience – a minimum of 3 years leading diverse teams of frontline practitioners with a proven track record of exceptional people management skills; 5+ years is a plus
  • LICSW or comparable licensure is required
  • Significant direct service experience (at least 5 years) with people experiencing homelessness, complex trauma, mental health challenges, substance use, and high-intensity case management. Substantive knowledge of the systems participants and Advocates navigate (housing programs, public benefit programs, MassHealth, Social Security, healthcare, the court system) is a plus.
  • Strong skills in project management, organization, time management, and delegation
  • Proven ability to juggle competing priorities and unexpected crises with calmness and clarity
  • Comfortable working in a small, less bureaucratic organization where plans can change quickly, and leaders are expected to pitch in when needed
  • Bilingual in Spanish or Haitian Creole is a plus

Skills and Experience

Seasoned, relational people leader who understands frontline work

• • Leads from a place of trust, setting clear expectations and holding people accountable with a personalized, caring approach
  • Appreciates the emotional intensity of the Advocate role and actively supports staff wellness, resilience, and sustainability
  • Skilled at “zooming in and out,” managing day-to-day program realities while also building stronger systems, processes, training, onboarding, and infrastructure
  • Builds the teams, culture, and processes that drive program quality and staff satisfaction

Deeply values-aligned, equity-centered, and participant-focused

• • Understands how race, class, gender identity, privilege, and power affect both participant experiences and workplace dynamics, with strong self-awareness about their own identities and assumptions
  • Able to consistently elevate participant voice while also balancing participant needs with staff wellbeing, particularly in complex situations involving harm, discrimination, or crisis
  • Moves with curiosity, humility, nonjudgment, and a willingness to admit mistakes, take responsibility, and change course when necessary
  • Willing to participate in employer-sponsored activities acknowledging, confronting, and dismantling racism and other issues of oppression and examining the impact of racism on themselves, on OTR, and in the community at large

Strong communicator, advocate, and trust-builder

• • Able to communicate clearly and transparently up, down, and across the organization, including explaining the rationale behind decisions and being clear about what is open for input versus already decided
  • Adept at elevating frontline perspectives in leadership-level discussions
  • Seeks out constructive feedback and receives it without becoming defensive
  • Able to engage in healthy conflict and have difficult conversations about performance or behavior in a direct but relational way

Schedule/Location, Compensation and Benefits

Schedule and Location: OTR’s normal business hours are 8 am - 4 pm on weekdays, and the duties of the position require the Director of Programs to be onsite in person at OTR’s headquarters in Cambridge 5 days per week.

The Safe Haven is open most Saturdays and most holidays. To ensure adequate staffing during all scheduled Safe Haven operations, the Director of Programs will participate in staff rotation for coverage on Saturdays and holidays (~once a month).

The position requires the ability to participate in occasional evening meetings and events.

Compensation and Benefits: This is a full-time, salaried, exempt position with an annual starting salary range of $95,000-$100,000, commensurate with experience and qualifications. On The Rise offers a generous benefits package, including:

• • 75% employer-sponsored health and dental coverage
  • Up to 5% retirement plan employer contribution
  • Annually 15 vacation days, 12 sick days, 12 paid holidays, 2 personal days. Vacation days increase to 20 days annually after completing your fourth year
  • 100% employer-paid short-/long-term disability plans, life insurance, and paid family and medical leave benefits
  • Continuing Education Benefit: OTR pays for 3 full work days and reimburses up to $600 per year for employees who have been employed for more than one year who wish to continue their education or take a course that is somewhat, but not directly related to work and/or is not covered by the training budget
  • Regular licensed clinical supervision provided onsite

Application Process, Timeline, and Additional Information

To Apply

Candidates must include a resume and a cover letter. We will not consider applications without a cover letter. Please respond specifically in your cover letter to these questions:

• • What excites you about working at On The Rise specifically?
  • Describe a time when you intentionally sought out and incorporated staff and program participant perspectives into a decision you made on behalf of a program you managed.
  • If taking the job would require a candidate to move to the Cambridge/Boston area, s/he/they should mention why that is a good fit for them at this time.

Upload required documents to: https://eostransitions.applicantpool.com/jobs/

Interview Process and Hiring Timeline

Applications will be accepted until the position has been filled, though priority will be given to applications received by October 13, 2026.

The interview process will include a Zoom screening interview and two on-site interview rounds, during which candidates will meet staff members, program participants, and board members. On The Rise hopes the hired candidate will begin work by/in January 2027.

Additional Information: Eos Transition Partners consultant, Erin Cox, is managing this search. All submissions will be acknowledged and are confidential. Submit any questions to Erin at erin@erinjcox.com.

On The Rise recognizes the importance and benefits of diversity in the workplace and the community. We are an AA/EOE, and we strongly encourage people who are bilingual/bicultural, people of color, people with disabilities, members of LGBQT communities, trans, and non-binary people to apply.