President (Interim to President & CEO)

Mission Statement

Using social and restorative justice principles, Five Keys provides traditionally underserved communities the opportunity to improve their lives by focusing on the Five Keys: Education, Employment, Recovery, Family, and Community.

Organizational Overview

Founded in 2003 by the San Francisco Sheriff’s Department, Five Keys Schools and Programs is a California-based nonprofit organization recognized as a national leader in social equity initiatives. With operations across 14 counties and more than 100 locations, Five Keys provides a continuum of services that includes:

• Public Charter High Schools in 16 jails and multiple community-based learning centers
• Housing Services, including shelters, navigation centers, and permanent supportive housing totaling over 2,800 beds statewide, as well as housing and voucher based housing programs
• Reentry and Workforce Programs, such as transitional employment and training through partnerships with agencies like Caltrans and Butte County Office of Education and Los Angeles City WorkSource Centers.
• Restorative Justice and Reentry Programs serving incarcerated and formerly incarcerated individuals and their families

Five Keys employs over 1200 staff, approximately half of whom are formerly incarcerated, and manages an annual budget of $135 million through local, state, and federal funding contracts.

At its core, Five Keys is committed to breaking cycles of poverty, homelessness, and incarceration by empowering individuals and families with access to education, housing, employment, and recovery support.

POSITION SUMMARY

The President will serve as the leader of the executive team during a defined transition period. Upon successful completion of this period, and contingent on approval by the CEO and Board of Directors, the President will assume the role of President & CEO. Throughout this transition, the President will collaborate closely with the Board of Directors and the outgoing CEO to ensure a smooth leadership change, maintain organizational stability, and advance the organization’s next phase of strategic growth.

The President will oversee the senior leadership team, steward relationships with key funders and partners, and champion Five Keys’ mission and culture of social justice, inclusion, and innovation. Our senior leadership team includes the COO, CFO, and CHRO, along with division leaders overseeing Housing, School, Programs, Transitional Employment, L&D, and Organizational Development.

JOB DUTIES AND RESPONSIBILITIES

Strategic Leadership

• Reports to and serves as the primary liaison to the Board of Directors ensuring informed decision-making and transparent communication.
• Provides visionary leadership to guide Five Keys’ next chapter of growth and sustainability.
• Collaborates with the Executive Leadership team on strategic priorities, policy decisions, and organizational direction.
• Ensures alignment of all programs, including education, housing, and workforce development, with the organization’s mission and goals.
• Communicates and collaborates with our law enforcement, government agencies and community partners.

Operational and Financial Oversight

• Oversees a multiple funding stream annual operating budget of approximately $135 million.
• Ensure fiscal integrity, accountability, and compliance with local, state, and federal regulations.
• Work with the Board to diversify and strengthen funding streams, including developing new philanthropic, private-sector, and donor-based revenue.
• Supports the professional growth and development of the leadership and management teams.
• Guides the organization’s response to challenges and crises, providing steady leadership to ensure stability and continuity of services across programs and operations.

Government Relations, Partnerships, and Advocacy

• Maintains, cultivates and strengthens key partnerships at the local, state, and federal levels, ensuring positive, collaborative relationships with public agencies, law enforcement and correctional departments, and elected officials.
• Advocates for policy and legislative priorities that protect and advance Five Keys’ mission and funding, actively engaging in coalition-building and public affairs.
• Monitors and responds to proposed legislation that could impact Five Keys’ operations, funding, or student populations, and leads proactive lobbying efforts to prevent or amend harmful legislation.
• Represents Five Keys in public policy forums, task forces, and advocacy initiatives at the local, state, and federal levels to advance social justice, educational access, housing stability, and reentry opportunities.

Communications & Public Representation

• Serves as the primary public representative of Five Keys, communicating the organization’s mission, values, and impact in a clear, compelling and professional way.
• Responds to media inquiries and engages with press, elected officials, community stakeholders, and the public in a manner that reflects transparency, respect, and dignity.
• Participates in panels, conferences, and community forums to elevate awareness of Five Keys’ work and the issues affecting the people and communities we serve.

Organizational Culture

• Promote Five Keys’ inclusive and restorative workplace culture, fostering trust, collaboration, and empowerment across departments.
• Upholds trauma-informed and equity-centered practices in all internal and external relationships.
• Advances Five Keys’ commitment to staff development, with an emphasis on internal promotion and leadership growth, including continuing support of the leadership and wellness initiatives implemented by the Learning and Development team.

Transition Leadership

• Partners with the current CEO throughout the transition period (2025–2027) to ensure continuity of leadership and institutional knowledge.
• After successful completion of the transition period, assumes all CEO responsibilities by July 1, 2025, at which point the current CEO will transition to an advisory and consulting role.
• Fulfills other duties as assigned

KNOWLEDGE AND SKILLS

• Proven executive-level leadership experience in a large, multi-faceted nonprofit, educational, housing, or social services organization.
• Demonstrated success managing complex funding streams and large budgets.
• Deep understanding of restorative justice, reentry, education, housing, or workforce development sectors.
• Strong financial acumen, policy awareness, and contract management expertise.
• Exceptional communication, collaboration, and relationship-building skills.
• High emotional intelligence and cultural and gender competence, with the ability to lead diverse teams and communities.
• Ability to work constructively with law enforcement leaders and facility commanders while advocating for the needs of Five Keys teachers, staff, and students.
• Advanced proficiency in Zoom, Microsoft Office, Google Workspace, and databases
• Able to maintain strict confidentiality and take all precautions when handling sensitive information
• Ability to effectively and efficiently work from home and independently, with high levels of self-accountability

EDUCATION AND WORK EXPERIENCE

• Master’s degree in Public Administration, Education, Business, or related field preferred (or equivalent leadership experience).
• Equivalent experience demonstrating advanced leadership, operational, and educational management capabilities may be considered in lieu of formal credentials.
• 10 years of progressively responsible executive leadership experience, ideally within education, social impact, reentry, workforce development, housing, or related community-based sectors.
• Proven success overseeing multi-site or complex organizational structures, preferably involving both educational and social service programs.
• Experience managing public funding, grants, and compliance requirements, including contracts with city, county, state, and federal agencies.
• Demonstrated record of leading organizational growth and strategic transformation, including experience guiding teams through change, mergers, or expansion.
• Strong background in equity-driven leadership, community engagement, and partnerships that advance social justice, educational access, and reentry opportunities.
• Experience collaborating with or reporting to a governing Board of Directors, and proven ability to cultivate strong relationships with diverse stakeholders, funders, and community partners.

PHYSICAL REQUIREMENTS  

• Frequent talking and hearing conversations
• Long periods of walking, sitting at a desk and/or computer station
• Lifting items that weigh up to 25 lbs; reaching, bending, carrying and stooping within the daily routine of tasks and activities

ADDITIONAL REQUIREMENTS

This position is contingent upon: 

• Satisfactory results of a Live Scan (criminal background investigation)
• Successfully obtaining jail clearance for positions working in county jails or probation locations
• Submitting proof of clear TB results. Results dated within 60 days prior to hire date are acceptable
• Must be a California resident located in Northern or Southern California, where Five Keys operates

Candidate Expectations

Applicants will be fully expected to have conducted thorough research on Five Keys Schools and Programs prior to any interview or engagement. This includes:

• Reviewing media coverage.
• Examining publicly available financial data.
• Based on readily available public sources, understanding current programs, partnerships, and areas of operation across education, housing, reentry, and workforce development.

WORK ENVIRONMENT  

• Moderate to high noise level
• Work environment varies from site to site
• Some personal safety risk working in underserved communities
• Must be willing and able to work in a correctional facility and travel throughout the area to community sites. 
• Must be willing and able to travel state-wide and at times out of state to various locations, meetings, conferences.
• Significant travel to Five Keys locations throughout California as needed.

BENEFITS

We offer medical, dental, and vision insurance, along with generous time off. Various pre-tax flexible spending accounts and retirement account 403(b) are available. Other Company-paid benefits, including an employee wellness program.

What it’s like to join our agency…

At Five Keys, culture matters. Culture is at the very core of everything we do and impact on a daily basis. We’ve made a commitment to building an inclusive culture that seeks collaboration over hierarchy to create empowered work teams. We serve vulnerable populations daily and we strive to approach everyone with compassion, patience and a trauma informed approach. We choose to push past discomfort to have difficult conversations to impact the greater good. This allows us the opportunity to collaboratively create an inclusive culture and transform the world around us.