Director of Strategic Initiatives and Operations

HIGH JUMP; Chicago (IL); Híbrido; USD 120.000 - 180.000; Jornada completa

Ventajas ofrecidas por este puesto de trabajo

Health insurance portion paid

Dental and vision coverage

401k with employer contribution

Disability & life insurance

Paid vacation & holidays

Wellness and ancillary benefits

Descripción de la vacante

HIGH JUMP seeks a Director of Strategic Initiatives & Operations to partner with the CEO and oversee core enterprise functions including finance, HR, risk, and governance. This role directs strategic plan execution, drives board governance activities, and unlocks organizational capacity.

The position is full-time in a hybrid work environment in Chicago, with a comprehensive benefits package and opportunities to shape the organization's mission and impact across staff and boards.

Formación

• Minimum 4–6 years of nonprofit operations, governance management, corporate administration, or strategic project management.
• Strong fluency with financial reports, budget monitoring, and accounting workflows.
• Bachelor's degree required; advanced degrees in relevant fields preferred.

Responsabilidades

• Serve as the primary operational partner and strategic liaison to the Board of Directors.
• Oversee operational cadence, meeting agendas, minutes, action-item tracking, and administrative support across all six Board committees.
• Direct quarterly preparation and distribution of Board packets, financial dashboards, and governance reports, co-owning cadence with Board Chair and Chief Officers.
• Partner with Board Chair, CEO, and Chief Officers to align board meeting agendas, financial reporting, and high-level strategy with organizational goals.
• Manage Board tracking systems, engagement metrics, directory updates, and onboarding workflows for new Directors.
• Communicate directly with Board members on strategic initiatives and executive projects.
• Own internal financial management and vendor accountability, including budgeting, forecasting, monthly reporting, variance management, and cash flow visibility.
• Manage HR benefits enrollment, payroll oversight, and HR compliance in collaboration with PEO/vendor.
• Oversee office operations, facility contracts, vendor management, and hybrid work rhythms.
• Create strategy for personnel systems, policies, HR compliance, and internal talent processes with PEO and leadership.
• Direct contracts, risk, insurance, and core operating infrastructure.
• Assist with administrative procedures and communication systems.

Conocimientos

Project management

Financial acumen

Emotional intelligence

Written & verbal communication

Strategic thinking

G-Suite

Microsoft Excel

Zoom

Board portals

Cross-team collaboration

Educación

Bachelor's degree

Advanced degree preferred

Herramientas

Board portals

G-Suite

Microsoft Excel

Zoom

Descripción del empleo

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 infrastucture (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.

POSITION STATUS:

This is a full-time position in a hybrid work environment. The generous, comprehensive benefits package includes employer paid health contributions over 75% of monthly enrollment costs, high quality dental and vision plans, 401k with a 6% employer contribution after one year, short and long term disability, life insurance, and many ancillary enrollment options. In addition to contractual time off and 14 holidays, the organization provides two additional and flexible weeks of paid vacation for all staff.

QUALIFICATIONS:

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

PRINCIPAL DUTIES AND RESPONSIBILITIES:

Board Governance & Strategic Liaison Management

• 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.

Enterprise Finance, HR & Operations Management

• 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.

Strategic Plan Tracking & Special Initiatives

• 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.

KNOWLEDGE AND SKILLS:

• Exceptional organizational skills and project management rigor, with the ability to manage multi-departmental projects and prioritize multiple tasks seamlessly.
• Strong financial acumen and operational analytical skills.
• 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.
• Forward-looking thinker who actively seeks opportunities, proposes solutions, and demonstrates proactive decision-making capabilities.
• 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.

OTHER ITEMS:

• 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.
• Will involve periodic work on Saturdays from September through May and some evenings throughout the year for board meetings and key events.
• High Jump is an equal opportunity employer and all qualified applicants will receive consideration for employment without regard to race, color, religion, sex, sexual orientation, gender identity or expression, pregnancy, age, national origin, disability status, genetic information, protected veteran status, or any other characteristic protected by law.