Director of Strategic Initiatives and Operations

High Jump•Chicago, IL

1d•Hybrid

About The Position

This position serves as the primary operational leader, financial and HR manager, and governance partner to the Chief Executive Officer (CEO). The Director of Strategic Initiatives & Operations supports the Office of the CEO, owns core enterprise infrastructure (HR, finance, risk) and serves as a strategic operational partner for a Board of Directors made up of over 40 Executives and civic leaders. By owning critical operational functions and directing strategic board governance strategy, this position ensures organizational excellence, drives strategic plan execution, and unlocks capacity for the organization’s staff, board, and CEO.

Requirements

Minimum of 4–6 years of progressive experience in nonprofit operations, governance management, corporate administration, or strategic project management.
Strong fluency with financial reports, budget monitoring, and accounting workflows, with the ability to collaborate effectively with internal accounting leads, human resources service providers, and Board committees.
Bachelor's degree required
Exceptional emotional intelligence, executive presence, hospitality, and discretion required to build relationships with high-level Board directors and external partners.
Expert-level written and verbal communication skills.
Advanced computer skills, including expertise in G-Suite, Microsoft Excel, Zoom, and board portal platforms.
Ability to work effectively within and across teams, driving accountability loops across leadership.
Must be a mission-driven person, committed to performing their functions so that the mission of the organization can be achieved.
Must prioritize building trust with colleagues, demonstrating professionalism, and working well with others.

Nice To Haves

advanced degrees in relevant fields (education, nonprofit, business) preferred.

Responsibilities

Serves as the primary operational partner and strategic liaison to the Board of Directors.
Oversees and coordinates the operational cadence, meeting agendas, minutes, action-item tracking, and administrative support across all six Board committees.
Directs the quarterly preparation, assembly, and distribution of Board packets, financial dashboards, and governance reports, co-owning the cadence with the Board Chair and all Chief Officers.
Partners with the Board Chair, CEO, and Chief Officers to align board meeting agendas, financial reporting, and high-level strategy with organizational goals.
Manages Board tracking systems, engagement metrics, directory updates, profiles, participation trackers, and formal onboarding workflows for new Board directors and non-director committee members.
Communicates directly with Board members on strategic initiatives and executive projects.
Owns internal financial management and vendor accountability, including managing annual budgeting, reforecasting, monthly financial reporting, budget-to-actuals variance management, monthly close, and cash flow visibility.
Manages the PEO/benefits vendor relationships, employee benefits enrollment, payroll execution oversight, and organizational HR compliance.
Oversees office operations, facility contracts, vendor management, hybrid work rhythms, and physical space management.
Creates the strategy and monitoring for roles and responsibilities with the PEO and Chief Officers related to personnel systems, employee policies, HR compliance, and internal talent processes.
Directs organizational contracts, risk, insurance, and core operating infrastructure.
Assists with the creation of administrative procedures and development of communication systems across the organization.
Serves as the central project manager for organizational goal-tracking, working in collaboration with High Jump’s Chiefs (Programs, Advancement, Executive Officer) to track progress against strategic plan priorities.
Leads major cross-departmental operational initiatives, including fiscal year calendar transitions, and risk management monitoring.
Serves as the administrative and operational continuity lead during executive sabbatical periods, maintaining institutional systems under a "Business as Usual" model.
Researches and follows up on incoming operational issues and concerns addressed to the CEO, including those of a sensitive or confidential nature.