Chief Executive Officer

Chief Executive Officer - Santa Ana, CA

Sterling Search Inc. has been exclusively retained to recruit the Chief Executive Officer for Working Wardrobes: https://www.workingwardrobes.org/

What We Do

Working Wardrobes helps people overcome barriers to employment by providing the skills, resources, support, and connections needed to achieve meaningful work. Through career preparation, coaching, training, professional clothing, and employer connections, the organization helps individuals build careers and create more stable futures.

About

For over 36 years, Working Wardrobes has helped more than 142,000 people achieve the dignity of work. Its mission is to help people overcome barriers to gainful employment whether those barriers are poverty, homelessness, substance recovery, incarceration, domestic violence, or other challenges. It serves seniors, youth, veterans, justice involved, and other people who wish to improve their lives through productive employment. Its comprehensive approach combines career readiness programming, professional wardrobing, one-on-one coaching, certification training, and direct employer connections to break cycles and build careers.

Working Wardrobes operates with a proven social enterprise model: three retail stores that both serve its mission and contribute meaningfully to its sustainability. With a team of 32 dedicated professionals, a $4.8M 2026 annual budget, and deep community partnerships, it has built an organization that transforms lives while operating with financial discipline and strategic focus.

The Opportunity

Working Wardrobes has become one of Orange County’s most respected and beloved nonprofits and established a powerful reputation for transforming lives through workforce development, career advancement, and economic empowerment.

Today, it is a modern, high-performing nonprofit with a people-centered culture and strong operational discipline. Through the adoption of the Entrepreneurial Operating System (EOS), the organization has strengthened accountability, sharpened its focus on measurable impact, and fostered a culture of continuous improvement and organizational excellence.

As Working Wardrobes celebrated its 35th anniversary in 2025, the organization achieved a series of notable milestones. It served more than 10,000 individuals, earned its fifth consecutive recognition as one of Orange County’s Best Places to Work and maintained its prestigious four-star Charity Navigator rating.

Working Wardrobes boasts a strong diversified financial revenue model that includes government contracts (24.5%), social enterprise (22%), philanthropy and fund development (29%), inkind support (8.5%), and investment and other income (16%) which positions them well to navigate the evolving funding landscape.

The organization is also supported by a high-performing, tenured executive leadership team and a strong bench of talented professionals who effectively manage the day-to-day operations of the organization. Together, they have built a sustainable operational foundation that positions Working Wardrobes for scalable growth, more innovative programs and partnerships, and increased community impact.

The next CEO will join Working Wardrobes at an exciting inflection point as the organization evaluates its next stage of visionary growth. In partnership with the Board of Directors and leadership team, the CEO will play a central role in shaping that vision, helping define future priorities, identify new opportunities, and lead the organization into its next chapter of impact and innovation.

Success for the incoming CEO will be defined by their ability to build upon this momentum: expanding philanthropic revenue, deepening strategic programmatic partnerships, and stewarding its assets.

Position Description

The Chief Executive Officer will lead Working Wardrobes through a pivotal moment of strategic evolution. The CEO will guide the organization as it builds a more diversified, donor-centered revenue model, building on the strong foundation Working Wardrobes has established.

Working Wardrobes has healthy reserves, strong programs, an engaged team, and a contributing social enterprise. The CEO will lead the organization toward sustainable growth through major donor relationships, foundation partnerships, and corporate engagement, while leveraging an actively supportive board and maintaining the business and operational excellence that has defined Working Wardrobes.

The CEO will serve as both an external ambassador and an internal champion of the mission. Fundraising should be grounded in genuine care for the people served and informed by regular, direct engagement with clients, staff, programs, volunteers, the board, and retail operations.

Primary Responsibilities

Organizational Leadership & Strategic Direction

• Lead the executive team in executing the organization's strategic plan, aligning programs, operations, and financial strategy with our mission to help people achieve the dignity of work.
• Lead measurable progress toward the established strategic goals for revenue, net operating income, clients reached, full-service clients achieving employment or secondary education, cash reserves and fundraising development targets. 
• Advance the long-term vision of a highly regarded, efficiently operating organization with an accessible presence throughout Southern California and a permanent headquarters that integrates services and operations.
• Foster a cohesive, inclusive workplace culture that attracts and retains exceptional talent across programs, operations, and leadership.
• Maintain and/or establish metrics and accountability systems that track program effectiveness, operational efficiency, and impact.
• Make strategic decisions about program priorities, service delivery, business expansion opportunities, and resource allocation in response to community needs and organizational capacity.
• Lead the strategic evaluation and integration of AI technologies as appropriate, to drive innovation, optimize operational efficiency, and maintain an organizational advantage.

Revenue Development & Financial Strategy

• Serve as Working Wardrobes’ chief fundraiser and implement a comprehensive development strategy that diversifies revenue across major and annual gifts, foundations, corporations, grants, planned and legacy giving, donor-advised funds, recurring giving, sponsorships, events, and strategic partnerships. Personally cultivate relationships with major donors and corporate prospects; set the tone for philanthropy across the organization.
• Partner with the Board and its fundraising committee to significantly expand the donor base, identify prospects, secure strategic introductions, cultivate donor relationships, support solicitations, and advance Board fundraising and ambassador commitments. Have a particular emphasis on high-net-worth individuals, family foundations, philanthropic advisors, corporate executives, and other high-value donors.
• Create and maintain donor relationships by implementing the structured donor stewardship program that strengthens retention, event participants, corporate partners, renewals, gift upgrades, multi-year commitments, re-engages lapsed donors, and strengthens donor loyalty through personalized engagement, impact reporting, recognition, and mission-immersion experiences.
• Expand planned and legacy giving, steward current Legacy Fund members, and advance an organizational endowment and other long-term philanthropic support.
• Establish a financial strategy that ensures sustainability, the ability to expand as desired, healthy cash reserves, and the capacity to invest in mission growth.
• Own achievement of and provide transparent financial reporting to the Board and Finance Committee, with clear analysis of revenue trends, budget performance, annual total income budget and net operating income budget, emerging risks, and financial health and implement corrective strategies when performance is below plan. Pursue opportunities to exceed established targets.

Community Engagement & Advocacy

• Serve as the voice and face of Working Wardrobes in the community, building awareness and support for our mission.
• Develop, maintain and expand strategic partnerships with employers, government agencies, education partners, and community organizations.
• Represent Working Wardrobes in advocacy efforts related to workforce development, poverty alleviation, and economic opportunity.
• Build authentic relationships with clients, volunteers, and community stakeholders to stay grounded in the realities we serve.

Board Partnership

• Work closely with the Board to ensure effective governance, strategic alignment, and fiduciary responsibility.
• Prepare comprehensive reports for Board and Committee meetings.
• Support Board recruitment, development, and onboarding efforts to ensure a cohesive, engaged governance structure.
• Support board committees in their work supporting Working Wardrobes mission and operations.

Required Qualifications

• A CEO who has led an organization of $3M+ and has been the driver of revenue growth or, a senior nonprofit leader from a $5M+ organization with executive-level fundraising responsibility and demonstrated success leading director-level and above teams.
• A minimum of 10 years in progressively responsible leadership positions within nonprofit, social enterprise, or community development sectors.
• Demonstrated success in major gift fundraising, foundation relations, and/or corporate development. Candidate should have personally closed $100K+ gifts and built relationships with institutional funders.
• Proven ability to lead and inspire a diverse team, with multi-functional experience including people leadership and operations. 
• Strong financial acumen: ability to read financial statements, manage budgets, establish financial strategy, and communicate financial performance clearly to boards and stakeholders.
• Entrepreneurial mindset: experience building new revenue streams, pivoting organizational strategy, or leading organizations through significant change.
• Authentic commitment to workforce development and economic opportunity. This role requires genuine passion for the people we serve.
• Excellent communication skills (written and verbal), cultural competence, and ability to build relationships across diverse stakeholder groups.
• Able and committed to serving as an active ambassador for Working Wardrobes in the community and at events which includes night/weekend events.
• Bachelor's degree or related relevant experience.
• Residence in Orange County/Southern California with the ability to build a sustained presence in Orange County given the role’s direct community, donor, employer, client and board engagement responsibilities.

Preferred Qualifications

• Experience using EOS or a comparable organizational operating system to drive strategic alignment, accountability, priorities, and execution.
• Demonstrated experience working in, living and/or leading an organization with a similar mission, such as workforce development, economic mobility, poverty alleviation, substance-use and recovery services, domestic-violence services, re-entry, homelessness, or related social-impact work.
• Master's degree in nonprofit management, business, or related field highly desired.
• Demonstrated experience of a value growth mindset to build and expand partnerships beyond present footprint and capability.

What We Value

• Mission-driven leadership: Your decisions are guided by our core purpose—helping people overcome barriers to gainful employment. 
• Strategic thinking and financial discipline: You balance bold vision with operational realism and fiscal responsibility.
• Collaborative leadership: You build strong teams, activate boards, and partner across sectors.
• Authentic engagement: You spend time with clients, staff, and community members. You lead by listening.
• Authentic philanthropy: You build donor relationships through genuine care for the people we serve and direct knowledge of the mission. Fundraising should be rooted in trust, connection, and demonstrated impact, not solely in financial transactions.
• Resilience and adaptability: You thrive in dynamic environments and lead others through change.
• Working Wardrobes Core Values: You lead with integrity, build thoughtful relationships, demonstrate humility while achieving results, and show grit in pursuing the mission.
• Equal Opportunity centered approach: You are committed to fostering an inclusive, diverse organization, focusing on the voices and needs of the people most impacted by barriers to employment.

Commitment to Equity

Working Wardrobes is committed to building a workforce that reflects the communities we serve. We actively encourage applications from people with lived experience of poverty, homelessness, incarceration, or other barriers to employment. We believe diverse leadership strengthens our organization and advances our mission.

Compensation & Benefits

• Salary: $185,000–$225,000 per year, plus bonus, commensurate with experience and background
• Medical, Dental & Vision Insurance
• Flexible Spending Account (FSA)
• Life Insurance
• 401(k) Plan
• Car Allowance
• Cell Phone Stipend
• Professional Development Support
• Collaborative and Mission-Driven Workplace
• Equal Opportunity Employer – Working Wardrobes actively encourages applications from candidates of all backgrounds.

TO APPLY PLEASE CONTACT:

• Katie Croskrey
• [email protected]
• 949-669-7378