Senior Associate, Principal Gifts & Engagement

At The Obama Foundation, our mission is to inspire, empower, and connect people to change their world.  We seek to build an active democratic culture where people are equipped and motivated to make change in the communities where they live, work, and play. Right here on the South Side of Chicago, we’re building a home for this vision, a global center for change with a range of opportunities - coordinated programming, community outreach events, educational moments, and more - that invite visitors from down the block or across the globe to turn hope into action.

Achieving our ambitious goals starts with an exceptional team built on our Hope to Action Values - Courage, Empathy, Integrity, Accountability, Community, Inclusivity, Pragmatism, Resilience, Imagination, and Hope. A Framework that anyone, anywhere, can use to build trust, activate participation, and expand opportunity in their community.

Purpose of the RoleThe Senior Associate, Principal Gifts & Engagement is a vital strategic and operational role designed to directly support the Vice President, Principal Gifts & Engagement in launching, building, and executing the Obama Foundation's inaugural principal giving strategy program. In this capacity, the Senior Associate serves as a core engine of the subteam, managing critical operational pipelines, driving comprehensive prospect briefing processes, and tracking metrics that empower the Vice President to effectively manage a premier portfolio of ultra-high-net-worth individuals focused on eight-figure, transformational investments. This role offers a unique opportunity for an entrepreneurial, highly detailed, and collaborative professional to build systemic infrastructure during a period of landmark growth.
The Senior Associate will work across divisions—liaising closely with Donor Relations, Events, Prospect Research, and Central Operations—to ensure that high-stakes interactions, personalized proposals, and executive or Board briefings are executed with absolute precision and alignment with the Foundation’s long-term sustainability goals.

Core Job Responsibilities

• VP Portfolio & Strategy Support: Partner directly with the Vice President to build out, operationalize, and track the long-term roadmap for the principal giving team. Manage the day-to-day coordination of the Vice President’s premier donor portfolio, tracking movement, multi-year engagement schedules, and critical next steps within the pipeline.

• Executive & Team CEO Liaison: Serve as a key operational bridge between the Principal Gifts subteam and Team CEO to streamline calendar alignment, track executive fundraising actions, and facilitate seamless execution of follow-up deliverables from high-priority meetings.

• Foundation-wide Collaboration & Workflow Integration: Partner extensively with programmatic, leadership, and operational teams across the entire foundation to unify fundraising strategies, cultivate a shared culture of philanthropy, and mobilize cross-functional resources for principal-level donor engagements.

• Briefing & Asset Management: Oversee the end-to-end briefing process for principal-level solicitations and meetings involving the Vice President, CEO, Board of Directors, or Obama network surrogates. Coordinate the development of highly personalized, visionary proposals, bespoke stewardship materials, and comprehensive briefing memos.

• Cross-Functional Collaboration: Act as the primary operational liaison between the Principal Gifts subteam and the Donor Relations & Events team to ensure top-notch execution of "white glove" donor experiences, custom pitch decks, and landmark on-site engagement opportunities at the Obama Presidential Center.

• Research Integration: Collaborate closely with the Prospect Research & Portfolio Insights subteam to monitor and synthesize profile analytics for top-tier prospects, ensuring that newly qualified leads are

• Perform other duties as assigned. 

Key Deliverables / Outcomes

• Top-notch operational execution and system maintenance during the foundational launch of the Principal Giving strategy team.

• On-time, meticulous production of high-stakes donor briefings, customized proposal materials, and follow-up communications supporting eight-figure investments. 

• Seamless multi-divisional coordination on high-level donor experiences, tracking deliverables precisely across Salesforce and shared trackers.

• Maintenance of real-time data integrity for principal-level portfolios, providing clear and actionable tracking metrics to the Vice President.

Required Qualifications

• A minimum of 3-4 years of professional experience in nonprofit development, strategic operations, or executive-level frontline fundraising support, preferably within a complex institution or capital campaign environment.

• Proven capability to handle hyper-sensitive donor information and navigate complex external and internal environments with absolute discretion, high integrity, and mature emotional intelligence.

• Excellent project management skills, with a track record of driving multi-layered processes across diverse, cross-functional teams under tight deadlines.

• Excellent written and oral communication skills, with sharp attention to detail required to produce board-ready briefings and high-quality stewardship collateral.

• Strong systems literacy, featuring advanced proficiency in donor management systems (Salesforce preferred) and the ability to utilize data analytics to inform fundraising strategy.

The salary range for this role is between $79,040 and $98,800.

This is a hybrid role based at our Chicago office.

Don’t check off every box in the requirements listed above? Please apply anyway! If you’re excited about this role but your past experience doesn’t align perfectly with every qualification in the job description, we encourage you to still consider submitting an application. You may be just the right candidate for this role or another one of our openings!

Equal Opportunity Employer

The Foundation is committed to creating a diverse work environment and is proud to be an equal opportunity employer. The Foundation does not discriminate on the basis of race, color, national origin, sex, gender identity, religion, sexual orientation, age, disability, parental status, veteran status, or any other protected status under applicable laws. We encourage individuals of all backgrounds to apply. If you are a qualified candidate with a disability, please e-mail us at [email protected] if you require a reasonable accommodation to complete this application.