Executive Director

Executive Director

Positive Directions–The Center for Prevention & Counseling

Westport, Connecticut

Lead with purpose. Build community. Change lives.

About Positive Directions

Founded in 1971, Positive Directions is a trusted, community-based nonprofit dedicated to supporting individuals, families, and communities through mental health treatment, substance use services, and prevention programs.

For over five decades, we have been a respected presence in Fairfield County—providing individual and family counseling (including telehealth), partnering with schools and municipalities, and leading prevention initiatives that strengthen resilience and promote healthy decision-making.

Today, Positive Directions is a thriving, mission-driven organization, licensed by DMHAS and deeply valued by the communities we serve.

The Opportunity

This is a unique opportunity to lead a well-established, highly respected organization at an important moment in its evolution.

We are seeking a dynamic, strategic, and hands-on Executive Director who brings both vision and execution—someone who can inspire others, strengthen operations, deepen community relationships, and drive long-term sustainability.

Reporting directly to the Board of Directors, the Executive Director serves as the organization’s chief leader—guiding strategy, operations, fundraising, and external engagement in service of our mission, staff, clients, and community.

Why This Role Now

Positive Directions is entering a pivotal moment—one that calls for bold, thoughtful leadership.

Demand for mental health and substance misuse services continues to accelerate across our region, placing community-based organizations like ours at the center of an increasingly urgent public health landscape. At the same time, Positive Directions has built a strong foundation: a trusted reputation, a committed and experienced team, engaged community partners, and a deeply supportive Board.

With this momentum comes opportunity.

The next Executive Director will step into a role with both stability and meaningful runway—well-positioned to strengthen financial sustainability, expand clinical and prevention programming, and elevate the organization’s visibility and voice in the community. This is not simply a leadership transition—it is a chance to shape the next era of Positive Directions. The right leader will bring clarity, energy, and strategic focus to guide growth, deepen impact, and ensure the organization continues to meet rising needs with excellence, innovation, and compassion.

What You Will Do

Champion the Mission

• Lead the organization in advancing its mission, vision, and long-term strategic direction
• Partner with the Board and staff to identify opportunities for growth, innovation, and impact
• Serve as a visible and engaged ambassador in the community

Inspire People & Culture

• Foster a culture of collaboration, accountability, equity, and excellence
• Build strong relationships across staff, leadership, and Board
• Recruit, support, and retain a talented and mission-driven team

Strengthen Sustainability

• Oversee the organization’s financial health, including budgeting and financial reporting
• Implement strong fiscal practices and ensure accountability
• Partner with the Board to expand fundraising and resource development efforts

Drive Fundraising & External Engagement

• Serve as the public face of Positive Directions
• Build and sustain relationships with donors, foundations, government agencies, and community partners
• Identify and pursue funding opportunities across individual, corporate, and institutional channels

Expand Visibility & Partnerships

• Elevate the organization’s profile and communicate its impact with clarity and confidence
• Lead outreach, marketing, and communications efforts
• Strengthen and expand strategic partnerships

Lead Effective Operations

• Oversee day-to-day operations, including human resources, compliance, and risk management
• Ensure compliance with all federal, state, and local laws, regulations, and licensing requirements
• Execute contracts, grants, and agreements on behalf of the organization

What You Bring

We are seeking a leader who is both strategic and hands-on—someone who can inspire confidence, build strong relationships, and translate vision into action.

Required:

• Experience in behavioral health, mental health, or substance misuse services
• Experience in nonprofit management or human services
• 5–7 years of leadership experience
• Demonstrated success in fundraising and resource development
• Strong financial and operational management skills
• Excellent written and verbal communication skills
• Confidence and effectiveness in public speaking

Preferred:

• Experience building organizational capacity and long-term sustainability
• Clinical or programmatic experience in behavioral health

Education

• Master’s degree in nonprofit management, public health, social work, mental health, or a related field required

Compensation & Benefits

• Salary range: $125,000 – $150,000, commensurate with experience
• Comprehensive benefits package, including:
• Health, dental, and vision insurance
• Generous paid time off (4 weeks PTO)
• IRA with employer match
• Eligibility for Public Service Loan Forgiveness (PSLF)

Why Join Positive Directions?

At Positive Directions, you’ll lead an organization that truly makes a difference—every day.

You’ll work alongside a passionate and committed leadership team and staff, a supportive and engaged Board, and a network of community partners who care deeply about this work. Together, you’ll help shape the future of an organization that is improving lives across the region.

How to Apply

Please submit your resume and cover letter to:

📧 [email protected]

• Include your last name in the filenames

To learn more, visit:

🌐 www.positivedirections.org

Equal Opportunity Employer

Positive Directions is proud to be an equal opportunity employer. We value diverse experiences and perspectives and are committed to creating an inclusive environment for all employees and applicants.