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.

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:

• 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

• 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

• 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

• 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