Lead, Service Delivery Management (Virtual Schools)

About the Role

The Lead, School Operations Manager aka: Director of School Operations (DSO) is a senior, enterprise‑level leader responsible for driving operational excellence across a portfolio of Connections Academy schools. This role partners closely with school leaders to ensure schools are compliant, sustainable, and positioned to deliver strong student outcomes—at scale.

The DSO is a leader of leaders, directly managing school principals and working alongside leadership teams to strengthen execution, build leadership capacity, and ensure the Connections Academy model is implemented with fidelity. This is a highly visible, high‑impact role requiring strong judgment, the ability to operate across multiple schools simultaneously, and comfort navigating complexity in a fast‑moving environment.

The DSO works in close partnership with cross‑functional teams—including School Success, Academic Outcomes, Finance, HR, and Operations—to translate strategy into disciplined, scalable execution while maintaining a strong focus on student experience and long‑term sustainability.

What You’ll Do

Lead Portfolio‑Level School Operations

• Directly manage and coach multiple school principals across a portfolio of virtual schools
• Establish clear operational expectations and accountability across schools while honoring local nuances
• Monitor operational health, compliance indicators, and engagement trends to proactively identify risks
• Hold school leaders accountable for execution of:
  • Academic improvement initiatives
  • Compliance, charter, and contract requirements
  • School‑year milestones and operational deliverables
• Provide structured, data‑informed coaching to strengthen leadership effectiveness and execution discipline

Enable Operational Sustainability & Enrollment Growth

• Partner with schools to ensure operational readiness to support enrollment growth
• Assess leadership capacity, staffing models, onboarding processes, scheduling, and systems readiness
• Identify operational constraints that could impact growth, persistence, or staff sustainability
• Strengthen retention‑supporting practices that improve student and staff experience
• Proactively identify and mitigate risks related to charter stability and renewal readiness

Drive School‑Year Readiness at Scale

• Ensure consistent execution of school‑year cycle activities across multiple schools, including:
  • School calendars and handbooks
  • Annual policy and process reviews
  • Summer school planning
• Identify pressure points impacting leaders and staff and coordinate mitigations across the portfolio

Build Leadership Capacity & Succession

• Serve as a leader of leaders, managing principals responsible for large, complex organizations
• Set clear performance expectations tied to operational excellence and strategic initiatives
• Conduct performance evaluations and support ongoing leader development
• Lead hiring, onboarding, and succession planning for school leaders
• Facilitate leadership development that cascades through leadership teams and staff

Support Boards, Authorizers & External Partners

• Support school leaders in engaging effectively with boards, authorizers, districts, and partners
• Prepare leaders for meetings by supporting agenda development, data review, and performance narratives
• Contribute to formal school leader performance reviews presented to boards, ensuring clarity and evidence‑based evaluation

Lead Change & Continuous Improvement

• Support schools through operational change as new products, services, and systems are introduced
• Drive adoption of enterprise processes while minimizing disruption to schools
• Contribute to continuous refinement of the School Operations operating model

What You Bring

Required Qualifications

• 3–5 years of proven leadership experience as a Principal or equivalent senior school leadership role
• Advanced degree in Education, Educational Leadership, or Management
• Demonstrated ability to lead leaders and operate effectively across multiple organizations
• Strong operational judgment and experience managing complexity at scale
• Excellent communication, executive presence, and relationship‑building skills
• Data‑driven mindset with a focus on results and accountability
• Comfort working in a technology‑enabled, virtual environment
• Ability and willingness to travel frequently

Preferred Qualifications

• Experience leading or supporting virtual or blended schools
• Experience working with charter schools, authorizers, or boards
• Background in large‑scale or multi‑site educational operations

Why This Role Matters

• Influence the success and sustainability of multiple schools serving students nationwide
• Partner closely with senior leaders to translate strategy into action
• Build strong, stable leadership teams that deliver consistent results
• Play a key role in enabling growth while protecting student experience and compliance