School Operations Jobs in Portland, OR (NOW HIRING)

Overview of the Role

As the Regional Operations Lead (ROL), you serve as a strategic and hands-on leadership partner supporting schools across the school operations, systems operations, and compliance domains. In this role, you help create the conditions that allow schools to thrive by strengthening operational consistency, improving systems execution, and ensuring campuses operate in a way that feels organized, reliable, and responsive for both staff and families. The region our schools in Washington, Oregon and Northern California.

A key aspect of this role is embracing smooth operations and accurate systems as a critical enabler of a strong parent and staff experience. Great ROLs understand that operations is not simply about task completion or compliance. It is about creating stability, trust, and consistency within the school community. When systems and processes function so effectively that complexity fades into the background, we consider that success.

You will play a key role in effectively managing and executing operational priorities including campus routines, staff scheduling, move-up and enrollment planning, student and staff records, operational compliance, tuition billing and collection, data accuracy, and responsible school-level practices. You will also collaborate closely with the corresponding central domain teams (e.g. School Operations, Compliance, Facilities, and Finance) to support ongoing development work such as improving operational resources for our school teams and onboarding and training processes.

Support may take many forms including coaching, modeling, guidance, accountability, thought partnership, connection to resources, and direct hands-on assistance when needed. The mix of support shifts based on the developmental stage of each school. Earlier-stage or less stable schools may require more hands-on operational partnership, while more established schools teams are coached to greater independence, stronger systems leadership, and long-term sustainability over time. In all cases, the goal is to help school leaders grow in their ability to independently lead strong operational systems and execution in close coordination with the broader regional team.

This work is deeply rewarding and deeply demanding. Strong ROLs balance strategic thinking with strong execution, support with accountability, and operational rigor with responsiveness and partnership while remaining closely connected to the realities of individual campuses and leadership teams. You should be energized by both strategic problem solving and the day-to-day work of helping schools execute with excellence.

Your Key Areas of Focus

Depending on the size, scope, and growth needs of the region, the Regional Operations Lead may report either to the Regional Manager (RM) or Assistant Regional Manager (ARM). In either structure, the ROL is responsible for driving strong execution and outcomes within the operations domain at the school-level in close partnership with their direct manager.

Key Job Responsibilities

School Operations Leadership

• Build excellent operational execution skills in school leaders across the region, including staffing coordination, scheduling effectiveness, move-up planning, campus routines, tuition billing practices, and day-to-day operational consistency.

• Strengthen school-level operational systems, routines, and leadership practices in ways that reduce operational friction and create organized, reliable, and positive experiences for both staff and families.

• Analyze operational, enrollment, and financial data to identify trends, assess school health, prioritize operational support needs, and drive action-oriented problem solving across schools.

Systems Operations & Compliance

• Ensure data integrity across school systems and platforms, maintaining accuracy, responsiveness, and effective execution at the campus level.

• Maintain clean and compliant student and staff records, licensing binders, and consistent compliance drills and procedures.

Coaching, School Partnership, and Leadership Development

• This role is not one-size-fits-all. The specific mix of responsibilities will vary meaningfully based on the developmental stage and needs of each school. In earlier-stage or less stable schools, this role may provide more hands-on partnership, at times working directly alongside school leaders or temporarily stepping in to help execute while leaders build skill and confidence. As school leaders and campuses grow in strength and stability, the role shifts toward greater strategic thought partnership, coaching, and accountability, with the goal of increasing school-level ownership, independence, and long-term sustainability over time. Most regions will include schools at multiple stages, and this role should expect to move fluidly between these modes based on where each school is and what it needs most.

• Coach school leaders toward stronger operational ownership, decision-making, prioritization, and execution by providing consistent feedback, guidance, accountability, and thought partnership to school leaders and regional team members.

• Provide clear written communication and follow-up, including visit recaps, action plans, accountability tracking, and operational updates.

• Serve as a hands-on support partner during urgent, sensitive, or high-impact operational situations.

• Onboard and development of new leaders, specifically as it relates to school and systems operational leadership, while building strong relationships across schools and central support teams to ensure schools receive timely, coordinated, and effective operational partnership.

Regional Partnership & Culture

• Be a visible and trusted regional partner by maintaining strong presence within school communities through campus visits, operational partnership, and relationship-building with school teams and families.

• Partner closely with regional and central teams (e.g., School Operations, Finance, Compliance, Facilities) to ensure schools receive coordinated support across operations, systems management, compliance, enrollment planning, and broader school health priorities.

• Act as a cultural leader who models Guidepost values through professionalism, responsiveness, accountability, operational excellence, and thoughtful leadership across the region.

What You Bring

• Passion for education and a deep belief in the lasting impact of a strong early childhood experience.

• Experience in school operations, systems management, compliance, campus administration, or related operational leadership roles requiring strong organization, execution, and problem solving.

• Experience providing feedback, accountability, and day-to-day guidance to others while helping drive strong operational execution and team effectiveness.

• Strong organizational and analytical skills with the ability to assess data and balance strategic thinking with hands-on execution.

• Exceptional relationship-building and hospitality instincts with the ability to build trust quickly, influence across functions, and create warm, welcoming experiences for families and school communities alike.

What we offer:

• Ongoing professional development
• A network of supportive peers and mentors who regularly share best practices
• Career growth and promotion opportunities
• A competitive salary
• Health, dental, and vision insurance
• Paid time off and paid holidays
• 75% tuition discount for two children at any school within our network (we serve children 3 months through 6 years old)

If interested, please apply below