Managing Director, School Strategy and Investments

Managing Director, School Strategy and Investments

Rochester Education and Development for Youth (READY)

Location: Rochester, NY, or Remote, with approximately 25% travel

Reports to: Chief Executive Officer

Who We Are

READY, Rochester Education and Development for Youth, is a 501(c)(3) strategic intermediary working to triple the number of Rochester K–12 students enrolled in high-quality schools, from approximately 3,000 students today to nearly 10,000 by 2034. We identify, evaluate, and invest in schools with the potential to deliver strong outcomes while helping build a broader ecosystem in which families are informed, educators reflect the diversity of the community, and policies and systems create the conditions for excellent schools to grow and thrive.

READY launched in 2023 and is entering an important period of growth. We partner with school leaders, families, funders, community organizations, business leaders, and other stakeholders who share our commitment to expanding educational opportunity and improving long-term outcomes for Rochester’s young people.

Position Summary

The Managing Director, School Strategy and Investments will develop and execute READY’s evidence-informed school investment strategy to increase the number of Rochester students attending high-quality schools. This includes identifying and evaluating promising founders, schools, and operators; structuring investments and support; overseeing launch, expansion, improvement, and technical assistance; monitoring performance; and determining where READY should continue, expand, adjust, or conclude its investment.

As a trusted partner to school leaders, the Managing Director, School Strategy and Investments will build strong relationships while maintaining clear expectations, surfacing risks early, and bringing sound judgment to complex decisions. This senior leader will also serve as a close thought partner to the CEO and contribute to broader organizational strategy, partnerships, and growth.

The role may be based in Rochester or remotely, with approximately 25% travel to Rochester and portfolio schools. Willingness to relocate to the Rochester area is welcomed but not required.

How You’ll Help

Set READY’s School Investment Strategy

• Build a deep understanding of Rochester’s school landscape, including school quality, enrollment patterns, community priorities, unmet needs, and opportunities for growth
• Develop and refine a multi-year school investment strategy aligned with READY’s goal of expanding access to high-quality schools
• Recommend how READY should balance investments in new-school incubation, local school expansion, national replication, and school improvement
• Translate the strategy into clear priorities, timelines, resource needs, and measures of success

Build the Pipeline of High-Quality Schools

• Identify and cultivate aspiring founders, strong local schools, and national operators with the potential to serve more Rochester students
• Oversee READY’s school incubation work, including the development of fellows, coordination of supports, and assessment of readiness for continued investment
• Partner with local schools considering grade expansion, enrollment growth, replication, or additional sites
• Work with the CEO to recruit high-quality school operators from other communities to explore expansion into Rochester
• Ensure prospective school models are responsive to Rochester’s students, families, and community context

Lead Diligence and Investment Decisions

• Develop consistent criteria and processes for evaluating prospective founders, schools, operators, and investments
• Assess academic quality, leadership capacity, financial sustainability, operational readiness, governance, community alignment, and implementation risk
• Distinguish between challenges that can reasonably be addressed through support and risks that should limit or prevent investment
• Prepare clear recommendations regarding grants, continued investment, expansion, replication, or changes in direction
• Establish appropriate milestones, reporting expectations, grant conditions, and accountability measures

Manage and Strengthen READY’s School Portfolio

• Serve as a trusted partner and primary relationship manager for school leaders, founders, and operators in READY’s portfolio
• Establish a regular cadence for monitoring progress, reviewing data, problem-solving, and providing strategic support
• Track performance across academic, enrollment, financial, operational, talent, governance, and implementation measures
• Surface risks early and determine when READY should offer additional support, revise expectations, or escalate concerns
• Make recommendations regarding renewed, expanded, modified, paused, or concluded investments
• Develop READY’s approach to supporting schools that need meaningful improvement or transformation

Oversee Technical Assistance and External Partners

• Identify the expertise and support required by founders, schools, and operators at different stages of development
• Source, select, and manage consultants, technical assistance providers, and other external partners
• Establish clear scopes of work, deliverables, timelines, budgets, and quality expectations
• Coordinate support across areas such as academics, operations, talent, finance, facilities, enrollment, governance, and authorization
• Monitor the effectiveness of external support and adjust the approach when services are not producing the intended results
• Build a strong network of local and national partners who can support READY’s school strategy over time

Strengthen Data, Learning, and Accountability

• Partner with READY’s Data and Operations Manager to build practical systems for tracking school and portfolio performance
• Analyze academic, enrollment, demographic, operational, and financial data alongside observations, stakeholder input, and community context to evaluate progress and inform strategy and investment decisions
• Develop dashboards, portfolio reviews, and other tools that support timely and disciplined decision-making
• Communicate findings and recommendations clearly to school partners, READY’s team, board members, and funders

Contribute to Organizational Leadership

• Serve as a senior advisor and thought partner to the CEO on school strategy, organizational priorities, and investment decisions
• Lead complex, cross-functional work involving READY’s talent, operations, communications, policy, and community-engagement functions
• Help determine the staffing, systems, partnerships, and resources needed as READY’s school portfolio grows
• Represent READY with school leaders, authorizers, funders, community partners, business leaders, and national education networks
• Contribute to a collaborative, mission-aligned culture that values initiative, quality, accountability, and enjoyment in the work

Qualifications

We recognize that strong candidates may bring different combinations of experience. Candidates who meet many, but not all, of the qualifications below are strongly encouraged to apply.

• Significant experience working in, leading, supporting, authorizing, investing in, or evaluating K-12 schools, including meaningful experience with charter schools
• Experience supporting schools that are launching, expanding, replicating, merging, or undergoing significant improvement or transformation
• Demonstrated ability to assess a complex landscape, set strategic priorities, and translate vision into actionable plans
• Strong judgment in evaluating school quality, organizational readiness, implementation risk, and the conditions necessary for schools to succeed
• Experience leading complex initiatives involving multiple stakeholders
• Experience managing people, leading a function, or overseeing consultants, vendors, and external partners
• Track record of building trusted relationships while maintaining clear expectations, accountability, candor, and follow-through
• Ability to analyze academic, enrollment, operational, financial, and qualitative information and use it to inform decisions
• Entrepreneurial mindset, including comfort with ambiguity, initiative, resourcefulness, and a willingness to engage directly in execution
• Strong communication skills and the ability to translate complex information into clear recommendations for varied audiences
• Deep commitment to expanding access to high-quality educational opportunities
• Commitment to equity, inclusion, and working effectively across lines of difference
• Willingness to travel approximately 25% of the time

Experience in one or more of the following areas is especially valuable: grantmaking or investment diligence, school improvement or turnaround, academic strategy, school operations, charter authorizing, portfolio management, data strategy, or recruitment of school founders and operators.

Location and Travel

This role may be based in Rochester, NY, or remotely. The Managing Director, School Strategy and Investments should expect to travel approximately 25% of the time to Rochester, portfolio schools, partner organizations, and relevant meetings or events.

Because success will require a strong understanding of Rochester and trusted relationships within the community, remote candidates must be prepared to establish a consistent and meaningful presence in the city.

Salary and Benefits

The anticipated salary range for this role is $160,000 to $180,000 annually. Placement within the range will reflect the selected candidate’s experience, skills, and alignment with the scope of the position.

READY offers a comprehensive benefits package that includes health coverage, employer-paid disability and life insurance, a 401(k) match of up to 5%, generous paid time off and organization-wide breaks, a $500 annual wellness benefit, and technology and home-office reimbursements. The Managing Director, School Strategy and Investments will also have opportunities to participate in national education and philanthropic networks and learn alongside leaders from other communities pursuing ambitious school-quality and growth strategies.

Application

Interested and qualified applicants should apply here. The application deadline is August 28, 2026. READY does not guarantee review of applications submitted after this date.

READY is an equal opportunity employer committed to equity, inclusion, and belonging. We actively seek to build a diverse team and strongly encourage candidates from backgrounds that have historically been underrepresented in education leadership and philanthropy to apply. READY does not discriminate on the basis of any characteristic protected under applicable federal, state, or local law, including race, color, religion, sex, pregnancy, sexual orientation, gender identity or expression, national origin, age, disability, genetic information, veteran or military status, or marital status.

READY offers a comprehensive benefits package that includes health coverage, employer-paid disability and life insurance, a 401(k) match of up to 5%, generous paid time off and organization-wide breaks, a $500 annual wellness benefit, and technology and home-office reimbursements. The Managing Director, School Strategy and Investments will also have opportunities to participate in national education and philanthropic networks and learn alongside leaders from other communities pursuing ambitious school-quality and growth strategies.