About CASSY
Counseling and Support Services for Youth (CASSY) provides a mental health safety net for more than 70,000 students across 37 school campuses in 10 districts throughout San Mateo and Santa Clara Counties, stretching from Gilroy to Redwood City. Through crisis intervention, ongoing counseling, and proactive mental health education, CASSY supports the social and emotional wellbeing of young people at no cost to students or families, eliminating the financial, logistical, and insurance barriers that too often prevent children from accessing care.
The need is urgent. One in five young people experience mental health challenges each year, yet the vast majority do not receive the support they need. CASSY's school-based model is central to its impact. By placing highly qualified, postgraduate therapists directly on school campuses, CASSY has demonstrated that students will seek help when it is available and accessible. On average, 20 to 25 percent of the entire student body receives support each year. When social and emotional obstacles are removed, academic achievement follows.
Founded in 2009, CASSY operates with a $3.4 million annual budget and a team of 70 employees. In 2024-2025, the organization expanded its reach through new partnerships with Mountain View Los Altos High School District, Khan Lab School, and Las Lomitas Elementary School District, a reflection of the growing demand for CASSY's model and the organization's momentum heading into its next chapter of leadership.
Its mission is to de-stigmatize mental health services and make supporting students' social and emotional wellbeing the norm in local schools, from kindergarten through high school graduation.
For more information on CASSY, please visit www.cassybayarea.org.
The Opportunity
CASSY seeks a dynamic and passionate Executive Director to lead the organization into the future. Reporting to a community-based Board of Directors, the Executive Director is responsible for both strategic leadership and day-to-day operations of the organization. Working with the Board and staff, the Executive Director will identify the resources necessary to sustain and expand CASSY's work and will serve as an ambassador for the organization throughout the community. This is an exciting opportunity for a committed professional to lead an organization with a stable infrastructure and a financial model that includes both philanthropic support and earned revenue to even greater levels of impact.
Specifically, the Executive Director will be responsible for the following:
Strategic Organizational Leadership
- Lead the process for planning, implementing, and evaluating short- and long-range strategy and goals, ensuring that future growth reflects the mission and values of the organization.
- Recruit, train, and empower a strong staff team, modeling a positive and healthy organizational culture.
- Ensure CASSY's sustainability through thoughtful budget planning and monitoring, regularly evaluating internal systems, policies, and procedures for efficiency and effectiveness.
- Oversee programs and services consistent with the mission, values, and goals of the organization, ensuring ongoing evaluation of best practices and effective systems for outcome tracking and contract compliance.
- Establish and cultivate partnerships with school districts and other community stakeholders to advance CASSY's mission and expand its reach.
Fund Development and Community Relations
- Develop and implement a diversified fund development plan including school partners, foundations, and public support.
- Manage the development of compelling, accurate, and timely funding proposals and reports.
- Serve as a credible and inspirational presence for CASSY in the community, maintaining relationships with stakeholders that build awareness of youth mental health needs and the organization's role in serving them.
- Direct branding and communication strategies that ensure CASSY's visibility among targeted constituencies.
Partnership with Board of Directors
- Provide the Board with the information needed to reach strategic decisions and formulate necessary policies.
- Ensure effective communication and linkages between Board and staff.
- Involve Board members meaningfully in fundraising activities.
- Support the Board in identifying, recruiting, and developing members with the skills to advance CASSY's mission and vision.
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 display the following professional and personal qualities, skills, and characteristics:
The ideal candidate will be an experienced leader who brings deep expertise in organizational leadership and a genuine dedication to CASSY's mission. They will bring strong financial management skills and a demonstrated ability to identify and secure resources for their organization. They will model the organization's values in all interactions, build and sustain meaningful relationships with school districts and funders, and always keep the needs of students at the center of their work. The ideal candidate will inspire and motivate staff to achieve ambitious goals and will bring both effective business practices and an entrepreneurial spirit in service of CASSY's mission.
Strategic Vision and Organizational Leadership
The ideal candidate demonstrates a track record of developing and executing multi-year organizational strategies that balance mission integrity with sustainable growth. They bring the entrepreneurial instinct to identify and act on emerging opportunities without losing sight of the student-centered mission. They are comfortable leading through ambiguity and organizational transition, and they bring a genuine, long-term investment in CASSY's trajectory and community relationships. As a people leader, they lead with emotional intelligence and self-awareness, modeling the heart-centered, collaborative, and authentic values that CASSY's staff and partners regard as foundational. They bring experience leading clinical or mission-driven teams with a management style that earns trust, restores morale, and motivates high performance without compromising staff wellbeing, and they demonstrate the ability to recruit, develop, and retain talent across both clinical and business functions. They communicate with clarity and conviction in writing, in front of diverse audiences, and in facilitated group settings, and are skilled at building consensus across stakeholders with competing priorities. They bring strong financial management skills and ensure that effective internal systems, policies, and data infrastructure are in place to support program quality, outcome tracking, and contract compliance.
Fundraising and Revenue Development
The ideal candidate brings demonstrated success in building and executing diversified fund development strategies, including foundation grants, individual donors, public funding, and earned revenue. They are skilled at cultivating and stewarding relationships with major foundation partners and identifying new philanthropic prospects aligned with CASSY's mission. Ideally, they are knowledgeable about emerging revenue models relevant to school-based mental health including insurance billing, university partnerships, government and state funding streams, and cost-share arrangements. They are able to serve as CASSY's primary external voice with funders, school district partners, and community stakeholders, clearly communicating impact and making a compelling case for support.
Relationship-Building and External Partnership Management
The ideal candidate is skilled at cultivating authentic, trust-based partnerships with school district administrators, superintendents, board members, and community leaders that reinforce CASSY's position as a thought leader in school-based mental health. They demonstrate the ability to represent the organization with credibility and warmth across diverse constituencies and approach new market development with an existing network or the demonstrated ability to build one quickly. They partner effectively with the Board of Directors, providing strategic guidance, engaging board members meaningfully in fundraising, and supporting board development and recruitment. Familiarity with school district structures and contract negotiations is a plus.
A Passion for the Mission
The ideal candidate brings a deep and authentic commitment to the mental health and wellbeing of young people and to the communities CASSY serves. They understand the urgency of the moment in school-based mental health and are motivated by the opportunity to lead an organization with CASSY's reach, reputation, and potential. They bring genuine humility and cultural awareness in their approach to serving young people from diverse cultural, economic, and educational backgrounds. A background in mental health, education, or a related clinical or human services field is preferred.
Compensation and Benefits
Salary is competitive and commensurate with experience. The salary range for this role is $180,000 – $200,000 with a generous benefits package.
Contact
DSG | Koya has been exclusively retained for this engagement, which is being led by Alexandra Corvin and Maleka Pensky. Express interest in this role by filling out our Talent Profile or emailing the search team directly at [email protected]. All inquiries and discussions are strictly confidential.
DSG | Koya 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.
CASSY is an equal opportunity employer. It is the policy of CASSY not to discriminate against any employee or applicant in any aspect of the employment relationship, including, but not limited to, matters of hiring, training, termination, compensation, terms, conditions, and privileges of employment on the basis of race, religious creed, color, national origin, ancestry, physical and mental disability or handicap, medical condition (as defined under California law), sex or gender (which includes gender identity, pregnancy, childbirth, or related medical conditions), age, sexual orientation, genetic information or characteristics (or those of a family member), status as a victim of domestic violence, sexual assault, or stalking, family status, marital status, military and veteran status, taking or requesting statutorily protected leave, or any other basis of the applicant or employee protected by law. In addition, CASSY prohibits the harassment of any individual on any of the bases listed above or any other characteristics protected under federal, state, or local laws.
About DSG | Koya
DSG | Koya, a DSG Global company, is the nation’s premier search firm dedicated to mission-driven leadership. Since its founding in 2004, DSG | Koya has had an exclusive focus on mission-driven clients and was founded on the belief that the right leader can transform an organization and have a deep and measurable impact on our world. DSG | Koya works with nonprofits & NGOs, responsible businesses, and social enterprises in local communities and around the world.
DSG Global is consistently recognized by Forbes on its top 10 list of “America’s Best Executive Recruiting Firms” and is an industry leader in recruiting transformational leaders for a changing world. The firm is deliberately different in its approach, with best-in-class teams who have decades of experience in cultivating inclusive leaders, understanding the dimensions of diversity, and building equitable teams.