(Hybrid) Project Specialist, President's Office

Job Descriptions:

Position Summary

The Project Specialist in the President’s Office plays a critical role in advancing the strategic priorities of The Chicago Community Trust by managing highly sensitive, high-impact special projects and key internal initiatives. This position operates at the center of the organization, supporting cross-functional collaboration, driving execution on leadership priorities, and ensuring seamless coordination of internal engagements such as Trust Connections and All Staff meetings.

This role requires exceptional judgment, discretion, and organizational skills, as well as the ability to navigate complex relationships and manage projects that often involve confidential or high-stakes information.

A successful project specialist’s core competencies include:

• Strategic thinking and execution

• Project management

• Relationship management and collaboration

• Adaptability and problem-solving

• Initiative and accountability

• Cultural competency and commitment to equity

Position Responsibilities

• Support senior leadership in advancing strategic initiatives and organizational priorities.

• Manage the planning, execution, and completion of high-priority, sensitive projects.

• Coordinate across departments to ensure alignment, accountability, and timely delivery of project milestones.

• Develop project plans, track progress, and proactively address risks or challenges.

• Prepare briefings, reports, and presentations for senior leadership.

• Manage the design and execution of priority organization-wide initiatives such as Trust Connections and All Staff meetings, as well as other special projects as assigned.

• Develop agendas, coordinate speakers, and ensure content aligns with organizational priorities and values.

• Partner with internal and external stakeholders to create meaningful, engaging experiences that foster connection, transparency, and shared purpose, such as volunteer activities, staff events, and neighborhood tours.

• Evaluate and continuously improve internal engagement efforts based on feedback, surveys, and organizational needs.

• Serve as a key liaison between the President’s Office and internal teams, ensuring clear communication and follow-through on execution of projects.

• Draft high-quality communications, memos, and talking points for internal and external audiences.

• Maintain strict confidentiality and exercise sound judgment in handling sensitive information.

• Improve processes and systems that support internal coordination and project execution.

• Manage multiple priorities simultaneously in a fast-paced, dynamic environment.

• Track and report on progress toward strategic goals and internal initiative outcomes.

• Report to multiple leaders, managing competing priorities and conflicting timelines as well as varying management styles.

• Other duties as assigned.

Required Experience:

Position Qualifications

• Bachelor’s degree or equivalent experience.

• 3-6 years of experience in project management, nonprofit or public administration, consulting, or a related field.

• Demonstrated ability to manage complex, cross-functional projects with multiple stakeholders.

• Exceptional organizational skills and attention to detail.

• Strong written and verbal communication skills.

• High level of discretion and ability to handle confidential information.

• Proficiency in Microsoft Office suite.

Preferred Qualifications

• Experience working in a nonprofit, philanthropy, or community foundation setting.

• Familiarity with equity-centered practices..

• Experience supporting senior executives or working within an executive office, and reporting to multiple leaders.

• Experience with project management software.

• Experience leveraging AI tools to enhance productivity, streamline workflows, and support project execution.

Keyword: consulting

From: The Chicago Community Trust