Director of Investments & Strategy

Chicago Beyond • Chicago, IL

2d • $125,000 - $150,000 • Hybrid

About The Position

The Director of Investments & Strategy is a senior leader responsible for shaping and executing Chicago Beyond’s investment strategy, leading the full investment lifecycle, driving organizational strategy in partnership with senior leaders, and ensuring that learning from our partners meaningfully informs our work. The role integrates investment strategy, impact measurement, and ongoing learning to ensure that Chicago Beyond deploys resources in ways that elevate new possibilities, challenge conditions holding systemic inequities in place, and generate actionable insights for the field. Reporting to the Chief Strategy Officer, the Director will lead the Investments team, steward the investments process from sourcing to contracting and partnership management, and ensure that our work is aligned with our mission, values, and long-term goals. In addition to what is outlined below, you will be responsible for other duties as assigned to support the goals and objectives of the organization.

Requirements

• Exceptional judgment and pattern recognition in complex ecosystems with the ability to see connections, identify underlying dynamics and leverage points, and synthesize information to guide strategic choices
• Demonstrated experience leading investment strategy, due diligence, partnerships, or complex strategic initiatives.
• Strong analytical and systems-thinking skills, with the ability to synthesize qualitative, quantitative, contextual, and narrative evidence.
• Strong strategic planning and project management skills, with the ability to set clear goals, develop actionable plans, and drive results.
• Demonstrated ability to develop KPIs, dashboards, measurement frameworks, and reporting mechanisms that drive insight and decision making.
• Exceptional communication and storytelling skills with the ability to translate complex ideas into compelling, structured narratives.
• Strong collaborator with the ability to translate strategy into actionable plans and deliver measurable results.
• Excellent leadership, management, and interpersonal skills, with experience building strong internal culture and high-performing teams.
• Strong strategic thinker who can connect the dots across issue areas, organizations, and ecosystem conditions.
• Highly organized and detail-oriented with the ability to manage multiple priorities in a fast-paced environment.

Responsibilities

• Identifying & Translating Trends into Investment Strategy
• Learning & Insight Capture
• Organizational Strategy & Strategic Initiatives
• Investment Process
• Investment Partnership Management
• Impact
• Systems & Tools
• Team Leadership & Management
• Stakeholder Engagement & Field Leadership

Benefits

• Chicago Beyond provides a comprehensive benefits package, including competitive medical, dental, and vision plans, a matching 401(k) program, and generous paid time off.

What This Job Offers

• Job Type: Full-time
• Career Level: Director
• Education Level: No Education Listed