Strategic Initiatives & Operations Director

HIGH JUMP; Chicago (IL); Hybrid; USD 120,000 - 180,000; Full time

Benefits offered by this job

Health insurance portion paid

Dental and vision coverage

401k with employer contribution

Disability & life insurance

Paid vacation & holidays

Wellness and ancillary benefits

Job summary

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.

Qualifications

• 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.

Responsibilities

• 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.

Skills

Project management

Financial acumen

Emotional intelligence

Written & verbal communication

Strategic thinking

G-Suite

Microsoft Excel

Zoom

Board portals

Cross-team collaboration

Education

Bachelor's degree

Advanced degree preferred

Tools

Board portals

G-Suite

Microsoft Excel

Zoom

Job description

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.