Regional Director of Operations, CT

About Achievement First

Achievement First (AF) is a nonprofit 501(c)(3) organization supporting 39 public charter schools across New York, Connecticut, and Rhode Island. For more than 25 years, AF has been recognized as one of the top tuition-free public charter school networks in the country. We are committed to creating schools of academic excellence within nurturing environments — schools that prepare students to be college-ready and to pursue and succeed in whatever paths they choose in life.

The majority of AF students are Black and Latinx children from low-income families, many of whom will be the first in their families to graduate from college. Across our network, we employ more than 2,200 staff members — 64% of whom identify as Black, Indigenous, or People of Color — who collectively educate nearly 15,000 students in Brooklyn and Queens, NY; New Haven, Bridgeport, and Hartford, CT; and Providence and Cranston, RI.

Our mission is to prepare every student to excel in college, career, and life; deepen their understanding of self and community; and lead lives of purpose. We believe in the limitless potential within our students and their power to shape a more just society. That belief drives our deep commitment to student achievement: we aim to set a high bar for learning and create warm, demanding classrooms where rigorous instruction is paired with the care, encouragement, and consistency every student deserves.

We are looking for a strategic and dynamic Regional Director Operations to join Team CT Leadership

Your Impact

The Regional Director of Operations (RDO) serves as a senior operational leader for Achievement First CT schools and regional initiatives. In addition to continuing to coach and develop Directors of School Operations (DSOs) and oversee operational excellence across schools, the RDOs will increasingly serve as the operational leads for regional priorities that require cross-functional coordination, strategic planning, and executive-level operational leadership.

This role requires balancing two interconnected responsibilities:

• Leading and developing strong school-based operations teams and ensuring schools meet operational performance outcomes.
• Serving as the regional operational lead for CT by driving key regional initiatives, coordinating across Network Support and regional teams, and supporting the Executive Director in operational strategy and execution.

The RDOs will act as key recommenders, problem-solvers, and change leaders for the region and will partner closely with the Executive Director, Regional Superintendent, Team School Operations, and Network Support teams to ensure operational decisions align to broader regional priorities and organizational strategy.

Reporting to the Executive Director of CT your responsibilities include but are not limited to:

DSO Development & Team Leadership

• Hold Directors of School Operations (DSOs) accountable to operational KPIs (Top Priority Assessment, Attendance/AUNR, budget, etc.) and coach to specific competencies (personal organization, delegation, prioritization)
• Own the full DSO development cycle:
• Kickoff stepback: Set outcome goals and learning/development goals for the year
• Bimonthly 1:1 stepbacks (with principal): Review progress, identify action steps, reassess L&D priorities
• EOY review: Final outcome assessment, reflection, and goal-setting for the following year
• Career conversations (Oct/Nov)
• Conduct two rounds of skip-level meetings annually (fall/spring) to identify high-potential ops talent and build the DSO pipeline
• Own talent and workforce planning — anticipating development needs and flagging recruitment gaps
• Execute PIPs and performance management with clarity and follow-through
• Lead weekly meetings covering: intentional skill-building, problem-solving, quick hits, accountability, and observation/feedback

Regional Culture & Principal Partnership

• Steward culture at both the school and regional level
• Lead regional initiatives and trainings
• Partner with principals and regional leadership to align on DSO performance, development, and the principal-DSO relationship

Network Support Liaison

• Serve as the single point of contact between schools and high-touch NS teams
• Synthesize feedback trends from schools to inform NS team improvement
• Collaborate with NS teams to problem-solve common challenges

Crisis & Continuity Leadership

• Lead response to safety incidents: convene huddles, activate protocols, facilitate debriefs
• Support schools navigating:
• Employee relations challenges
• Significant understaffing
• Facilities emergencies
• Acute staff/student culture issues
• Co-location crises

Cross-Functional Leadership & Regional Operations

• Manage regional budget and financial stewardship
• Own regional procurement, contracts, and service provider relationships (transportation, nursing, food services, etc.)
• Recommend and manage regional investments
• Manage student services
• Serve as primary liaison to non-program NS functions (operations, finance, facilities, talent/HR)

Portfolio Management

• Serve as a key regional collaborator on portfolio management work streams, including growth, closures, and research and analysis

Skills and Characteristics 

• A commitment to Achievement First’s mission, deep love of operations, and an unwavering belief that all students can and will succeed 
• A multi-year track record of leading an exemplary operations at a school or portfolio of schools, preferably schools that serve similar populations to Achievement First 
• Demonstrated success in coaching and developing other operational leaders 
• High bar of excellence for operational functions and a desire to urgently close gaps between current reality and expectations 
• Results oriented, with strong data analysis and action planning skills 
• Ability to inspire, influence and negotiate with a large number of diverse stakeholders
• Team player: maturity, humility, strong work ethic, follow-through, sense of humor, willingness to respond positively to feedback and a “roll-up-my-sleeves” attitude. 

Educational Background and Work Experience: 

• A bachelor’s degree; advanced degree a plus 
• Successful formal school leadership experience as a director of school operations, principal or assistant principal of a school with a proven, multi-year track record of operational outcomes 
• Occasional weekend or evening work and willingness to travel to our schools and offices across our three states as needed in required

Compensation

Achievement First sets salaries through a lens of equity, and based on the requisite skills, education, and experience relevant to the role. Salary for this role is $150,331.20. In order to uphold our commitment to equity, Achievement First does not negotiate pay. Achievement First offers to all regular, full-time employees a comprehensive benefits package that includes paid time off, medical, dental, vision, and life insurance, a 403(b) retirement benefit package with match, and paid Family Leave.