ORGANIZATION
Founded in 2016, SchoolHouse Connection (SHC) is the nation's leading nonprofit dedicated to overcoming homelessness through early care and education. SHC works to ensure that children and youth experiencing homelessness, from prenatal through postsecondary education, have access to the educational opportunities and supports they need to thrive and break the cycle of homelessness.
SHC advances its mission through a unique combination of strategic policy advocacy, practical assistance, and grassroots partnership. Working alongside young people, families, educators, early childhood providers, institutions of higher education, service organizations, and policymakers, the organization develops practical solutions that improve educational access while driving lasting systems change at the local, state, and national levels.
Today, SHC's national network spans all 50 states and the District of Columbia and includes educators, school district homeless liaisons, state coordinators, higher education leaders, early childhood providers, researchers, advocates, service providers, and youth with lived experience. Together, they are working toward a future where every child and young person experiencing homelessness has access to high-quality education and the opportunity to achieve lasting stability.
To learn more about SchoolHouse Connection, please visit www.schoolhouseconnection.org.
ABOUT THE ROLE
SchoolHouse Connection (SHC) is entering a new phase of growth. As our work expands across programs, policy, communications, partnerships, and emerging state-based initiatives, we are creating a new senior leadership role to ensure our strategic priorities translate into coordinated, high-quality execution across the organization. Reporting directly to the Executive Director, the Senior Director of Strategic Execution serves as the organization's chief integrator, building and leading the planning processes, operating rhythms, and accountability systems that keep teams aligned, focused on the highest-impact work, and moving forward together.
This role is ideal for a strategic systems-minded organizational leader who excels at bringing clarity to complexity, helping leaders make thoughtful tradeoffs, and enabling others to succeed. Working in close partnership with the Executive Director and senior leadership team, the Senior Director will strengthen cross-functional collaboration, improve organizational effectiveness, and build and maintain the infrastructure that allows SchoolHouse Connection to scale its impact while staying true to its mission.
WHAT YOU’LL DO
1. Turn strategy into clear priorities and coordinated plans
- Partner with the Executive Director to translate SHC's strategic vision into a focused set of organizational priorities with clear outcomes, ownership, success measures, and realistic timelines that reflect organizational capacity.
- Translate annual goals into coordinated execution plans by aligning work across teams, identifying dependencies, and sequencing initiatives for maximum impact.
- Maintain visibility across programs, policy and advocacy, communications, operations, and emerging initiatives to identify misalignment, duplication, capacity constraints, and execution risks before they affect progress.
- Facilitate cross-functional prioritization and planning conversations that help leaders make thoughtful tradeoffs, align resources, and stay focused on the highest-impact work.
- Build shared visibility into organizational priorities, ownership, dependencies, timelines, and progress to strengthen alignment and coordination across teams.
- Ensure day-to-day decisions consistently reinforce SHC's strategic priorities and mission, prioritizing organizational impact over individual preferences or functional interests.
- Continuously assess organizational capacity and execution progress, recommending adjustments as priorities evolve or new opportunities emerge.
2. Build and lead the systems that enable organizational execution
- Design, lead, and continuously improve SHC's core planning and management processes, including annual retreats, quarterly planning, leadership meetings, progress reviews, and cross-functional planning cycles that keep the organization aligned and moving forward.
- Develop and maintain practical operating systems, planning tools, and dashboards that increase transparency, strengthen execution, and support better decision-making without creating unnecessary bureaucracy.
- Design and facilitate effective meeting structures and operating rhythms that focus leaders on the highest priorities, produce clear decisions, and drive consistent follow-through.
- Strengthen organizational communication and information flow by documenting key decisions, clarifying ownership and next steps, and ensuring teams have the visibility they need to coordinate effectively.
- Establish and lead consistent planning, meeting, and accountability practices, including agendas, decision logs, meeting norms, and follow-up processes that reinforce transparency and shared accountability.
- Lead organizational learning and continuous improvement by introducing structured debriefs following major initiatives, events, and milestones and translating lessons learned into stronger organizational practices.
- Regularly assess planning processes, meeting structures, and operating systems, identifying where greater discipline will improve execution and where simplification will better support the work.
3. Serve as strategic partner to the Executive Director
- Frame organizational tradeoffs, sequencing decisions, and capacity constraints with clear recommendations that support effective decision-making.
- Proactively coordinate cross-functional work so the Executive Director is no longer responsible for managing day-to-day organizational connections.
- Reduce the Executive Director's operational and decision-making burden, allowing her to focus on vision, relationships, fundraising, and long-term organizational strategy.
- Provide candid counsel grounded in sound judgment, organizational priorities, and a commitment to what is best for SchoolHouse Connection rather than individual preferences or perspectives.
4. Drive accountability and solve cross-team challenges
- Surface and resolve cross-functional challenges related to timing, scope, sequencing, ownership, decision-making, and coordination before they impede execution.
- Design and maintain practical systems that make priorities, commitments, deadlines, cross-functional dependencies, and project progress visible, enabling leaders to stay aligned and accountable without creating unnecessary bureaucracy.
- Partner with the Executive Director to strengthen clarity, disciplined execution, and shared accountability across the senior leadership team.
- Establish and reinforce clear organizational norms for decision-making, communication, accountability, and quality that enable teams to work consistently and effectively across functions.
- Cultivate a culture of accountability grounded in trust, transparency, shared ownership, and high standards, where commitments are consistently met or proactively renegotiated.
- Facilitate difficult conversations with respect, discretion, and sound judgment, preserving strong relationships while advancing organizational priorities.
- Bring calm, clarity, and composure during periods of ambiguity, competing priorities, or organizational urgency, helping leaders make thoughtful decisions and keeping teams focused on what matters most.
5. Help lead SHC’s next phase of growth
- Lead organizational expansion through a two-year state-based pilot, ensuring the work is integrated with SHC’s broader priorities.
- Oversee evaluation and continuous improvement of the pilot to inform SHC’s growth model and future operating practices.
- Document and codify plans, decisions, and lessons learned to support consistency, learning, and scalability.
- Ensure state-based expansion is fully integrated into organization-wide planning, priorities, and operating systems.
- Develop evaluation and learning practices that capture lessons from the pilot and strengthen SHC's future growth strategy.
WHAT SUCCESS LOOKS LIKE IN YEAR 1
- Create a shared set of organizational priorities that guide decision-making across every team.
- Build and maintain planning and accountability systems that ensure commitments are visible, tracked, and completed.
- Establish and lead a durable operating cadence that keeps teams aligned without requiring constant Executive Director involvement.
- Help senior leaders make thoughtful tradeoffs around organizational capacity before issues become urgent.
- Reduce the Executive Director's operational coordination burden, allowing greater focus on organizational strategy, external relationships, fundraising, and long-term growth.
- Ensure SHC's state-based expansion is fully integrated into organizational planning while documenting lessons that strengthen the organization's future growth model.
Requirements
The strongest candidates will demonstrate the following leadership qualities:
- Mission over ego: Consistently prioritizes SchoolHouse Connection's mission, organizational impact, and collective success over personal recognition, control, or being right.
- Impact over process: Builds systems and operating rhythms that enable better outcomes, knowing when more structure is needed, when less is needed, and why.
- Relationship-centered leadership: Builds trust through humility, respect, discretion, transparency, and alignment with the organization's values.
- Composed under pressure: Brings steadiness, perspective, and clear decision-making in fast-moving, high-stakes situations, helping others remain focused and effective.
Required experience and knowledge
- At least 10 years of experience in senior operations, strategy, chief of staff, or organizational leadership roles, preferably in complex, national education nonprofits.
- Demonstrated success translating strategy into execution across multiple teams or functions.
- Experience designing and leading planning processes, operating rhythms, and progress-monitoring systems.
- Experience leading teams through growth, change, or increased complexity.
- Strong understanding of nonprofit operating models, capacity constraints, and cross-functional coordination.
- Experience serving as a strategic partner to an Executive Director, CEO, Chief Operating Officer, or equivalent executive leader.
- Experience building organizational operating systems and management infrastructure in growing organizations.
- Demonstrated success facilitating cross-functional decision-making among senior leaders.
- Experience balancing organizational agility with disciplined execution.
Key strengths for success
- Exceptional systems thinking and pattern recognition.
- Strong judgment and facilitation skills, including the ability to frame options, tradeoffs, and recommendations for senior leaders.
- Excellent project and portfolio management skills.
- Clear, concise writing and communication skills.
- High emotional intelligence and the ability to build trust, navigate ambiguity, and strengthen relationships across diverse teams.
- Strong judgment about when greater structure will improve execution and when flexibility will produce better outcomes.
- Ability to influence without relying on supervisory authority.
- Exceptional facilitation and consensus-building skills.
- Ability to identify organizational patterns, capacity constraints, and execution risks before they become problems.
- Comfort navigating difficult conversations that improve organizational effectiveness.
- Ability to build practical systems that people actually use.
- Executive presence characterized by humility, discretion, composure under pressure, sound judgment, and an unwavering commitment to the mission over personal recognition.
Benefits
This position is full-time, offers a competitive salary range of $152,000 - $190,000, and robust benefits including work from home, flexible schedule (with occasional required travel), generous leave, health insurance reimbursement, 403(b) plan with employer contribution, and professional growth opportunities. More details can be provided upon request.
TO APPLY
Please submit a resume online at https://apply.workable.com/j/37049FB27E.
SchoolHouse Connection provides equal employment opportunities to all employees and applicants for employment without regard to race, ethnicity, color, religion, sex, national origin, age, disability, sexual orientation, gender identity or expression, medical condition, genetics, veteran status, or any other characteristic protected by applicable federal, state and local laws. Upon request, reasonable accommodations in the application process will be provided to individuals with disabilities.
