Director of Investments & Strategy

About Chicago Beyond

Chicago Beyond is a national philanthropic organization that addresses systemic inequity by backing solutions led by those closest to the issues. Since our inception in 2016, Chicago Beyond has invested more than $65 million in catalytic funding in over 250 individuals and community organizations while leading national systems change initiatives. Because there is no single barrier to equity, Chicago Beyond engages in opportunities across philanthropy, justice, health, and beyond.

We address systemic inequity in three ways:

• Investments: We make catalytic investments to increase the impact of solutions led by those closest to the issues.
• National Initiatives: We lead national initiatives in partnership with change makers to challenge and reshape the status quo.
• Insights: We provide insights to disrupt and reimagine “systems as usual” and share learnings on equitable funding, practices, and policies.

About Chicago Beyond’s Partners

Through flexible funding, strategic support, and an equitable approach, Chicago Beyond’s partners are strongly positioned to provide high-quality services to their communities and reshape systemic structures to improve lives.

Our investment partnerships include:

• Multiyear Investment Partners: Through multimillion-dollar, flexible grants and partnership support, we work to increase the impact of solutions led by those closest to the issues.
• Rapid Response Fund: This fund quickly delivers unrestricted grants to organizations and individuals with solutions for their own communities across the country. Our investments strengthen partners’ wide-ranging work.
• Leader in Residence: The Leader in Residence program offers funding and support to selected leaders, empowering them to develop innovative, transformative ideas that create meaningful impacts in targeted communities.

Chicago Beyond was founded by Liz Dozier, a nationally renowned former educator and high school principal. Chicago Beyond’s innovative and impactful work has been featured on both the local and national level from the Chicago Tribune to the Clinton Global Initiative to Aspen Ideas Festival and Stanford Social Innovation Review. For more information on Chicago Beyond, please visit chicagobeyond.org.

Position Details

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.

Key Responsibilities:

1. Identifying & Translating Trends into Investment Strategy: Evaluate ecosystem trends and partner learnings to identify emerging patterns, insights, and high-leverage opportunities for impact. Lead Chicago Beyond’s investment strategy, ensuring alignment with mission, values, systemic opportunities, and organizational priorities. Develop and refine investment theses that articulate the problem, systemic levers for change, and the potential models that can drive change.
2. Learning & Insight Capture: Ensure the consistent capture of learnings from diligence, partner conversations, and field experiences. Build structures (templates, trackers, debriefs, reflection routines) that surface insights early and reliably before they become obvious to the field. Lead the organization in identifying how these insights can shift practices in the field. Redesign approaches to partner learning conversations that unlock new ideas, strengthen outcomes, and generate insights that drive systems change, future external insights products, and our voice in the field. Develop approaches for internal learning conversations that translate insights into strategic shifts and organizational priorities.
3. Organizational Strategy & Strategic Initiatives: Partner with the Chief Strategy Officer to lead organizational strategic planning, ensuring strategy remains adaptive and informed by partners, ecosystem shifts, and internal reflection. Lead major strategic initiatives from concept to execution, managing cross-functional timelines, resources, and deliverables. Identify emerging opportunities, risks, and areas requiring strategic shifts and advise senior leadership on recommended next steps. Work with Communications and leadership to translate investment insights into compelling strategic narratives for the field.
4. Investment Process: Lead the Investment’s team sourcing and due diligence process. Ensure diligence processes are rigorous, timely, equitable, and anchored in Chicago Beyond’s values. Oversee development of investment proposals and materials for decision-making, ensuring they reflect clear logic & structure, systemic framing, and alignment with Chicago Beyond’s goals. Facilitate cross-team collaboration to integrate insights, contextual analysis, and trends into investment recommendations. Oversee the contracting process and establish strong processes for contract management, timelines, deliverables, and disbursement. Continuously improve the investments process and approach.
5. Investment Partnership Management: Oversee partnership management across the full portfolio, ensuring investment partners have a high-quality, trust-based experience. Identify, track, and surface patterns, risks, opportunities, and strategic adjustments. Define and steward partnership models, expectations, engagement rhythms, and learning structures. Manage relationships with Fellows and Leader in Residence partners.
6. Impact: Lead Chicago Beyond’s qualitative and quantitative impact measurement approach across investments and key bodies of work. Define KPIs, impact frameworks, and approach for data collection & capture. Develop and optimize dashboards, tracking tools, and evaluation systems that synthesize qualitative, quantitative, and contextual data. Develop methods to identify signals of systemic change. Produce memos, insights briefs, and leadership updates that inform decisions and shape field influence.
7. Systems & Tools: Own and improve systems that support investment processes, impact tracking, and strategic execution (e.g., CRM, trackers, dashboards). Ensure documentation, data, and learning are organized, accessible, and high quality. Lead continuous improvement of tools and processes that strengthen decision-making, coordination, and organizational learning.
8. Team Leadership & Management: Lead and develop the Investments team, providing clear direction, coaching, development, and accountability. Foster a culture of curiosity, collaboration, equity, trust, and excellence. Ensure team members are supported, aligned, and empowered to execute effectively.
9. Stakeholder Engagement & Field Leadership: Cultivate relationships with proximate leaders, funders, community partners, and experts to strengthen strategy and ecosystem context. Support Chicago Beyond’s field influence by ensuring patterns and learnings are surfaced for future insights and communications work.

Qualifications:

• 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.

Working at Chicago Beyond

We are an agile, ambitious team with diverse experience across various sectors. We thrive on challenging each other and continuously learning, united by our passion for equity and lasting impact. If you are an entrepreneurial individual looking to join a dynamic community with significant opportunities to grow and shape what you do, then this will be a perfect role for you. Please note that this role is based in our Chicago office and operates in a hybrid work environment.

Our values guide our work.

• Always Equitable – People in our communities face unimaginable obstacles to achieving their fullest human potential. So, we must fight for equity, not equality.
• Incessantly Urgent – The simple fact is that lives are literally at stake right now. The unacceptability of the situation requires our relentless bias to action in order to accelerate our impact.
• Endlessly Creative – To dramatically impact the lives of our youth and communities, we must employ imagination to augment or replace the usual, typical, and predictable.
• Stubbornly Audacious – Entrenched challenges require disruptive ideas boldly applied. We must be unafraid to embrace risks.
• Uncompromising Integrity – How we achieve our mission is equally as important as our mission. We must do right by our youth, our communities, our partners, our teammates and ourselves.

Benefits

The salary range for this role is $125,000 - $150,000. Chicago Beyond provides a comprehensive benefits package, including competitive medical, dental, and vision plans, a matching 401(k) program, and generous paid time off.

Chicago Beyond is an equal opportunity employer and strongly encourages applications from people of color, persons with disabilities, LGBTQ+, and other underrepresented applicants.