Position: Director, Program-Related Investments

Reports to: Chief Financial and Investment Officer

Location: Los Angeles, CA, hybrid (in the field, in-office minimum two days, and work from home)

Position Overview

The Director, Program-Related Investments is a senior member of the Foundation’s finance and investment function, with primary responsibility for the Foundation’s $45 million Program-Related Investment (PRI) portfolio, sourcing and closing approximately three to five new investments annually. This is a rigorous investment role: the Director leads strategy development, manages the deal pipeline, and oversees underwriting, structuring, and portfolio monitoring, working with external advisers who provide back-office support.

What makes this role distinctive is where it sits organizationally. The Director is a structural participant in Weingart’s Strategy and Impact team, at that table not as a programs generalist but as a finance and investment voice — helping Program Directors identify where flexible capital can complement grantmaking, surfacing PRI-eligible opportunities collaboratively, and sourcing deals with people who have deep community relationships. Part of this role’s frontier is helping sharpen Weingart’s own thinking about what an economic-justice lens on capital deployment concretely means: who is excluded from capital and why, what terms actually build community wealth rather than merely avoid harm, and how to structure deals that interrupt rather than reproduce exclusion. For the right candidate, this is a rare leadership opportunity at the frontier of foundation practice, where financial rigor, deep roots in Southern California communities, and strategic creativity converge.

Beyond the PRI portfolio, the Director partners with the CFIO to advance Weingart’s “One Foundation” approach – contributing to its goal of deploying capital coherently across grantmaking, PRIs, and mission-aligned endowment investments. The Director attends all Investment Committee meetings — leading presentation of PRI recommendations and portfolio updates, addressing any Committee questions, and contributing programmatic and community perspective across the broader agenda.

Position Responsibilities

1. Leading PRI strategy. Proactively develop, refine, and advance the Foundation’s PRI strategy in collaboration with the CFIO, Foundation leadership, and the Investment Committee. Bring strategic recommendations to leadership and the IC. Track emerging trends and innovations in community development finance and mission-aligned investing, and translate them into actionable strategic options for the Foundation.
2. Sourcing and pipeline development. Build and maintain a robust PRI pipeline through proactive outreach, field relationships, and close collaboration with Program Directors. Serve as a structural participant in Strategy and Impact team strategy discussions, bringing an investment perspective to community work: helping Directors identify where flexible capital can complement grantmaking, surfacing PRI-eligible opportunities they encounter in the field, and jointly developing the pipeline that results. Part of this function is building Directors’ fluency in recognizing and evaluating flexible capital opportunities — deepening the team’s collective capacity to see and act on them over time.
3. Underwriting and deal structuring. Develop investment recommendations on prospective PRIs, directing diligence — project and operational feasibility, financial modeling, risk assessment, repayment analysis, and governance and management evaluation — conducted with the support of the Foundation’s external advisers. Structure creative, mission-aligned financial transactions that serve both the Foundation’s goals and its partners’ best interests. Present recommendations to leadership and the Investment Committee, leading the Committee through questions and follow-up.
4. Deal closing and execution. Manage the closing process for approved investments, working with external advisers and legal counsel to finalize loan documents, reporting requirements, disbursement schedules, and other closing conditions. Ensure deals close on terms that are financially sound, fair to all parties, and that reflect the Foundation’s commitment to community partners alongside its own fiduciary responsibilities.
5. Partner engagement. Serve as the primary point of contact on PRI matters for active investees, in coordination with colleagues where the broader relationship is shared. Engage each partner as a resource and thought partner over the life of the investment: proactively checking in rather than only responding to requests, and connecting organizations to other capital, technical assistance, or relationships that can support their work.
6. Portfolio monitoring and management. Oversee the active PRI portfolio with support from external advisers: reviewing financial and narrative reports, evaluating amendment and modification requests, monitoring repayment schedules, and flagging risks or opportunities to leadership. Manage the closeout process for completed investments. In conjunction with the Controller, ensure accurate accounting and reporting for the PRI portfolio.
7. PRI impact reporting. Working primarily in coordination with the CFIO and with support from external advisers, develop impact reports for the PRI portfolio in close collaboration with the Foundation’s Impact and Learning function. Support leadership in contextualizing Weingart’s approach to program-related investing and communicating its outcomes to internal and external audiences. This work is a contribution to a shared institutional effort, developed in coordination rather than independently.
8. Partnering with the CFIO on integrated capital. Partner with the CFIO to advance the One Foundation approach to capital deployment, identifying opportunities where Weingart’s tools — grants, PRIs, and mission-aligned endowment investments — can work in concert to advance shared goals.
9. Partnering with the Strategy and Impact team. Serve as a standing investment resource for the Strategy and Impact team, working alongside Program Directors to identify, evaluate, and develop PRI opportunities that emerge from community relationships and field work. This partnership is built on reciprocal learning: the Director brings investment expertise to programmatic conversations, and the team deepens the Director’s understanding of community context and strategy.
10. Representing the Foundation. Represent the Foundation in the community development finance and mission-aligned investing field: participating in peer convenings, serving on discussion panels, and maintaining relationships with CDFIs, community lenders, and other field actors that inform the Foundation’s strategy and pipeline.
11. Contributing broadly. Manage external advisers supporting PRI operations. Perform special assignments and duties as needed.

Dedication to our mission

Genuine commitment to racial, social, and economic justice and to the communities the Foundation serves. Alignment with our core values and a demonstrated interest in the intersection of finance and community impact.

Relevant experience

Significant experience in investment analysis, underwriting, or structured finance, with a demonstrated record of negotiating and closing complex transactions — recoverable grants, guarantees, subordinate debt, blended capital stacks, or special-purpose-entity structures — including direct negotiation with institutional co-lenders and legal counsel. Ideally with exposure to mission-aligned, community development, or impact investing contexts. Relevant backgrounds include community development finance (CDFI), nonprofit lending, real estate finance, impact investing, and mission-aligned investment management. We highly value candidates whose experience includes lived knowledge of the communities we serve, in addition to demonstrated financial and underwriting capability.

Skills, knowledge, and abilities

Required

1. Strong financial analysis and modeling skills: the ability to assess organizational and project feasibility, structure transactions, evaluate repayment risk, and produce analysis that holds up to rigorous scrutiny.
2. Experience structuring and underwriting creative, impact-oriented financial transactions — loans, guarantees, recoverable grants, or other flexible capital instruments — is required.
3. Comfort being directly involved in closing a transaction: working through final negotiation points, documentation details, amendments, covenants, and closing conditions alongside counsel.
4. The ability to develop independent recommendations and contribute effectively in strategic and governance contexts, alongside the judgment to engage colleagues and leadership when doing so maintains alignment, surfaces important considerations, or advances a culture of transparency and collaboration.
5. Proficiency with standard financial and office software.

Preferred

1. Deep familiarity with Los Angeles and broader Southern California, including its communities and the local community development finance landscape.
2. Knowledge of community development finance and the evolving landscape of mission-aligned investing: trends, innovations, key actors, and the regulatory and tax environment affecting PRIs.
3. Direct experience in CDFI lending, impact investing, or mission-aligned investment management, including PRI or investment roles at peer foundations.
4. Experience monitoring an active loan or investment portfolio after closing: reviewing financial and narrative reports, evaluating amendment or modification requests, and managing distressed-asset or workout situations.
5. Experience presenting to a governing board or investment committee.
6. Strong written and oral communication skills, including the ability to translate complex financial analysis into clear, accessible recommendations for non-finance audiences.
7. Ability to manage multiple transactions and workstreams simultaneously, with strong attention to detail and follow-through.

Working style

1. Proactive and self-directed: comfortable developing strategic recommendations and bringing them forward.
2. Collaborative across functions: genuinely interested in working alongside Program Directors as a thought partner, not just a transaction executor.
3. Rigorous and mission-committed in equal measure: unwilling to sacrifice analytical quality for mission alignment, or mission alignment for financial tidiness.
4. Curious, open to innovation, and committed to ongoing learning in a field that is still evolving.

Diversity, equity, and inclusion

Demonstrated experience working effectively with people from diverse backgrounds, and a strong commitment to an inclusive environment that places a high value on equity. Understanding of and sensitivity to the communities the Foundation serves is a genuine asset in this role.

Education

An MBA, CFA, or equivalent graduate or professional credential in finance, economics, business, or a related field is preferred. Demonstrated capability and relevant experience are weighted alongside formal credentials; candidates without a graduate degree but with strong track records in community development finance or mission-aligned investing are encouraged to apply.