Regional Executive Director, Connecticut, Achievement First

About Achievement First

Founded in 2008, Achievement First (AF) is a nonprofit 501(c)(3) organization that supports 41 public charter schools across New York, Rhode Island, and Connecticut. Recognized as one of the nation’s top charter school networks for nearly 25 years, AF remains dedicated to continuous improvement, programmatic innovation, and sustainable growth to enhance student outcomes. The network serves over 15,000 students, the majority of whom are Black and Latinx, qualify for free or reduced-price lunch, and will be the first in their families to graduate from college.

Achievement First’s mission is to prepare every student to excel in college and career, develop a deep understanding of self and community, and lead lives of purpose. Grounded in the belief that all students have unlimited potential and the power to shape a more just society, AF recently launched a five-year strategic plan focused on three key areas: Enhanced K-12 Programming, Equity-Centered Talent, and Community Engagement.

Learn more about the mission, vision, and schools by visiting www.achievementfirst.org.

About the Regional Executive Director, Connecticut

Reporting to the Superintendent, the Regional Executive Director – Connecticut will oversee K-12 programs across 10 schools in New Haven, Bridgeport, and Hartford, ensuring strong local decision-making, advocacy, and support. Serving as the face of Achievement First in Connecticut, the Regional Executive Director will build on the organization’s legacy of excellence since the first school opened in New Haven in 1999. The Regional Executive Director will guide our strategy to address the unique conditions in Connecticut that will enable Achievement First to foster supportive school environments and build a culture of academic excellence. Additionally, the Executive Director will play a critical role in  supporting external initiatives, cultivating and supporting four governing boards, pursuing charter reauthorization, addressing infrastructure and facility needs, and building closer relationships in the three distinct cities where AF schools operate. 

By driving the regional vision and strategy for academic excellence, operational efficiency, and school culture, the Regional Executive Director will lead a high-performing team, including 3-5 direct reports, dedicated to delivering exceptional learning experiences for every student. Additionally, they will oversee a sustainable organizational model that meets the growing demand for AF schools. As a member of the extended executive team, the Regional Executive Director will collaborate with program departments to ensure the region has the financial, operational, and talent resources necessary to thrive.

Key Responsibilities and Duties

Lead and develop a high-performing team to deliver and accelerate an exceptional education experience for all students (50%)

• Directly manage Regional Superintendents to deliver on the instructional vision across the region. 
• Drive results across the region, including progress tracking, monitoring, and reporting, holding team and self accountable to short and long-term outcomes and ensuring instructional excellence, and a joyful culture.
• Foster a high-performing, equitable, and inclusive team culture that motivates each team member to thrive and make impactful contributions to AF’s mission.
• Support, coach, and develop the team by providing targeted 1-on-1s, feedback, accountability, mentorship, and growth opportunities.
• Plan and execute high impact professional development sessions for school leaders across the region
• Promote the AF talent strategy and recruit, develop, and retain high-performing teachers, school leaders, and regional support team members.
• Model and promote transparent communication within the team and across departments to build trust, ensure alignment and collaboration, and drive results. 

Serve as the public face of Achievement First Connecticut (25%)

• Collaborate with the Chief Executive and Superintendent to maintain and cultivate strong, engaged, and active regional boards.
• Build and promote the AF Connecticut brand within the statewide market as the face of the region, as evidenced by relationships with board members, parents, funders, community members, and stakeholders.
• Build coalitions, relationships, and partnerships with key community leaders, elected officials, and peer educational leaders in support of the organization’s mission and goals.
• Support fundraising efforts and community engagement initiatives, in partnership with the network development team. 

Champion the region’s strategy and success (25%)

• Collaborate with the Executive Leadership Team to hone the region’s strategic priorities to fit the context of the three distinct geographies.
• Enact the network’s strategic plan by developing and implementing a regional plan to accomplish key priorities.
• Deliver the core instructional approach, teacher development, and student experience across ten K-12 schools in Connecticut.
• Partner with the Superintendent to set clear multi-year operational, financial, and academic goals for the region, ensuring a sustainable organization at all levels.
• Champion the AF organizational culture and model the core values that apply across every school for both students and adults. 
• Manage change across the region and invest internal and external key stakeholders in strategic evolutions, always ensuring that students and academic excellence are at the center of decision making.
• Identify opportunities for cross-functional, cross-organizational collaboration to ensure the relational health and coherence of the organization.

Key Competencies and Skills

Instructional Leadership

• Deep knowledge of evidence-based instructional practices and interventions with diverse learners, including demonstrated practice for improving student learning.
• Drive the academic vision and implement academic programming across all schools.
• Maintain visibility in the schools and work collaboratively with regional superintendents and school leaders.
• Accurately assess team and individuals’ skills, identify development needs, and provide feedback and support to improve practice, build capacity, and maximize talent.
• Effectively balance the tension between individual school leaders' needs and the need for coherence across the region and the network. 
• Demonstrate integrity while fostering collaboration among teams, departments, and key stakeholders.

Impact and Influence

• Advocate for and serve as the key connector between the Executive Team and the regional team.
• Facilitate and secure buy-in for a clear and compelling vision of organizational excellence for AF Connecticut.
• Navigate politically complex structures, relationships, and dynamics to enable thoughtful decisions and positive outcomes for students.
• Build coalitions and authentic relationships across lines of difference (race, gender, age, socioeconomic background, LGBTQ status, etc.) and work collaboratively with diverse stakeholders at all levels of the organization  
• Proactively identify, address, and resolve conflicts to facilitate mutually beneficial solutions and support effective change management.

Decision-making, Problem Solving and Results Orientation

• Exhibit outstanding critical thinking skills, including the ability to analyze data, identify trends, pinpoint problems and root causes, ask probing questions, and develop innovative solutions.
• Possess a deep understanding of systems-level operations, management, and organizational design in order to deliver desired outcomes for the region. 
• Analyze the conditions for change and articulate the vision for change to inspire and create ownership, buy-in, and accountability within the region. 
• Lead effectively even in times of ambiguity and adapt and respond to unexpected challenges.
• Exhibit a strong focus on goals, accountability, and results; set clear metrics for success.

Extraordinary Communication

• Communicate clearly and consistently, tailoring written and verbal messages for the context and audience. 
• Listen actively and compassionately with an open mind, seeking to fully understand what makes the regions and each community unique before establishing the direction forward.
• Address matters of equity, race, and bias in decision-making with clarity, confidence, openness, empathy, and historical context.
• Solicit, elevate, understand, and value--either through personal experience or empathy--the perspective of a wide variety of stakeholders. 
• Respond to feedback and concerns in a timely and empathetic manner.

Minimum Qualifications

• Bachelor's degree required; advanced degree preferred. 
• At least 5-7 years of CMO or district level supervision experience, including managing multiple schools and school leaders and delivering exemplary outcomes for low-income students and students of color.
• Holds or is on a pathway to hold principal and/or district level certification in CT or in a state with reciprocity.
• A demonstrable commitment to pursuing equity.
• A strong track record of experience and results as a trusted member of an organization’s senior leadership team.
• Knowledge of public school policy and law, procedures and management. 
• Spanish language proficiency is a plus.

Location and Travel

Must reside in Connecticut and be able to travel frequently between schools in New Haven, Bridgeport, and Hartford. Periodic travel to internal meetings in NYC or Stamford, CT will also be required.  

Achievement First sets salaries through a lens of equity based on the requisite skills, education, and experience relevant to the role.  The salary for this key leadership position is competitive, and set at $218,926.05. In addition, all regular full-time employees receive a comprehensive benefits package, which includes paid time off, medical, dental, vision, and life insurance, a 403(b) retirement plan with an employer match, and paid family leave.

Achievement First is an equal-opportunity employer and encourages applications from diverse candidates. Achievement First does not discriminate in any aspect of employment on the basis of race, color, ancestry or national origin, religion, sex, sexual orientation, gender identity, gender expression, marital status, disability, veteran status, genetic information, or age.