Executive Director at Rolling Start, Inc.

Position Summary

The Executive Director serves as the chief executive officer of Rolling Start, Inc. and is responsible for the overall leadership, strategic direction, administration, and day-to-day operations of the organization. Working in close partnership with the Board of Directors, the Executive Director ensures that Rolling Start fulfills its mission and delivers high-quality Independent Living services consistent with the Independent Living philosophy, consumer control principles, and all applicable federal and state requirements.

The Executive Director is responsible for organizational sustainability, including program oversight, staff leadership, fiscal management, compliance, fundraising, and community engagement across Rolling Start’s service areas.

Essential Duties And Responsibilities

Organizational Leadership & Strategic Direction

• Provide visionary and mission-driven leadership to advance Rolling Start’s strategic priorities, organizational growth, and community impact.
• Develop plans, goals, and innovative approaches that strengthen Rolling Start’s programs and service delivery.
• Promote and advance the Independent Living philosophy and ensure consumer involvement in decision-making processes.
• Maintain strong working relationships with the Board of Directors, including providing recommendations on policy, operations, and strategic direction.
• Provide the Board with full and timely reporting on organizational performance, program outcomes, fiscal health, and operational challenges.

Program Oversight & Compliance

• Ensure delivery of the Five Core Services of the Independent Living Program: Information and Referral, Peer Support, Independent Living Skills Training, Advocacy, and Transition Services.
• Oversee program planning, implementation, evaluation, and continuous improvement.
• Ensure compliance with all grant, contract, reporting, performance, and audit requirements.
• Oversee preparation and submission of required reports to funders, auditors, regulatory agencies, and the Board.
• Track and analyze consumer and community data to assess needs, identify service gaps, and guide priorities.

Fiscal Management & Internal Controls

• Establish and maintain sound fiscal policies, systems, and internal controls to ensure responsible stewardship of Rolling Start’s assets and funding resources.
• Develop and oversee organizational budgets, forecasting, cost estimates, and cash flow monitoring.
• Provide regular financial reporting to the Board, including monthly revenue/expense updates and variance analysis.
• Monitor expenditures, authorize purchases consistent with policy, and promptly report fiscal concerns or discrepancies to the Treasurer and Board.
• Oversee contract negotiation and management with public and private funding sources.

Fundraising & Resource Development

• Provide leadership for fundraising strategies and long-term revenue sustainability.
• In collaboration with the Board and Fund Development Chair, develop an annual fundraising plan with measurable goals.
• Maintain donor files, track fundraising progress, and ensure timely cultivation and solicitation follow-up.
• Strengthen donor retention by updating and expanding donor lists, renewing current donors, and re-engaging lapsed donors.
• Support development and implementation of donor engagement strategies, including: at least two annual donor mailings; outreach to new donor prospects; major donor cultivation ($500+); and community-based giving initiatives (membership or monthly giving programs).
• Plan and oversee donor events and community engagement opportunities, including appreciation events or program tours as appropriate.

Staff Leadership & Human Resources Management

• Recruit, hire, supervise, evaluate, and support staff in alignment with personnel policies and applicable employment law.
• Build and maintain a positive, collaborative, accountable organizational culture.
• Promote professional development, training, and leadership growth opportunities for staff.
• Ensure personnel policies and procedures remain current, compliant, and reflective of best practices.
• Ensure Rolling Start has a competent, well-trained team delivering high-quality services.

Community Relations, Advocacy & Partnerships

• Serve as Rolling Start’s chief ambassador and primary representative in the community.
• Build and maintain strong relationships with community organizations, advocacy coalitions, corporate partners, government agencies, and stakeholders.
• Represent Rolling Start in federal, state, and local systems advocacy, legislative engagement, and disability rights initiatives.
• Promote public awareness of Rolling Start’s mission, services, and Systems Change priorities.
• Maintain effective communication and collaboration across Rolling Start’s service areas, including San Bernardino, Inyo, and Mono Counties.

Governance & External Engagement

• Support the Board in fulfilling its governance responsibilities and ensuring organizational accountability.
• Attend relevant statewide Independent Living or advocacy meetings and conferences, including California Foundation for Independent Living Centers (CFILC) quarterly conferences or designate a representative as appropriate.
• Participate in advocacy efforts, including supporting or opposing legislative initiatives with Board approval.
• Perform other duties as assigned by the Board of Directors.

Knowledge, Skills, Abilities & Characteristics

• Commitment to the Independent Living philosophy, consumer control, and cross-disability inclusion.
• Strong leadership and management skills, including ability to motivate staff and foster teamwork.
• Proven ability to manage complex nonprofit operations with professionalism and accountability.
• Strong financial management and budgeting skills, including internal controls and reporting.
• Strong grant and contract management experience, including compliance and performance oversight.
• Fundraising and donor engagement experience, with demonstrated ability to grow financial support.
• Knowledge of disability civil rights laws, disability systems, and advocacy strategies.
• Ability to work effectively with culturally diverse communities and stakeholders.
• Strong written and verbal communication skills, including public speaking and relationship-building.
• Strong organizational and time-management skills with ability to manage multiple priorities.
• Proficiency in Microsoft Office (Word, Excel, PowerPoint) and comfort using technology and data systems.
• Ability to mediate, negotiate, and resolve conflicts in a constructive manner.
• Demonstrated emotional intelligence and a people-centered leadership style, including the ability to listen deeply, communicate respectfully, and respond with empathy to the needs of staff and individuals with disabilities served by Rolling Start.

Minimum Qualifications

• Bachelor’s degree in Rehabilitation, Counseling, Psychology, Sociology, Social Work, Public Administration, Nonprofit Management, or a related field (Master’s degree preferred).
• Minimum of 5–7 years of relevant leadership and supervisory experience, preferably in disability services, human services, Independent Living, or nonprofit administration.
• Demonstrated knowledge of the Independent Living movement and consumer-directed services.
• Experience managing grants, contracts, compliance reporting, and organizational operations.
• Demonstrated fiscal management experience, including budgeting and financial reporting.
• Demonstrated fundraising and donor development experience.
• Strong written communication skills, including grant writing, donor communications, and formal reporting.
• Ability to pass a criminal background check (as required).
• Ability and willingness to work occasional evenings/weekends and travel throughout the service region and state as needed.

Preferred Qualifications

• Lived experience as a person with a disability.
• Demonstrated history of disability rights advocacy and systems change leadership.
• Master’s degree in a related field.
• Experience working closely with boards of directors and supporting governance functions.
• Legislative advocacy and public policy engagement experience.
• Demonstrated commitment to diversity, equity, inclusion, and disability justice.
• Experience working across diverse cultural, social, political, and business sectors.

Working Conditions

• Regular onsite work required; occasional evenings and weekend commitments may be necessary.
• Travel throughout San Bernardino, Inyo, and Mono Counties, and periodic travel statewide for meetings and conferences.
• Ability to manage multiple projects simultaneously and work effectively under deadlines.

Equal Opportunity & Reasonable Accommodation

Rolling Start, Inc. is an Affirmative Action/Equal Opportunity Employer. People with disabilities and individuals from historically underrepresented communities are strongly encouraged to apply. Reasonable accommodations will be provided to qualified applicants and employees with disabilities to ensure equal access to the application process and employment.