Manager of Annual Giving

Communities In Schools of Chicago•Chicago, IL

2d•$63,000 - $65,000

About The Position

At Communities In Schools (CIS) of Chicago, we believe students can enhance their learning when their needs are met. Every day, we partner with Chicago Public Schools (CPS) and hundreds of community organizations to bring no-cost, high-quality programs directly to schools. These programs help students stay focused, engaged, and on track to graduate. During the 2025–26 school year, we are serving 80,000 students across 250 schools, connecting them to life-changing support from arts and academic enrichment to health and mental wellness services. And we need your help to make it happen. We're looking for a Manager of Annual Giving to join our team. If you're passionate about building meaningful donor relationships, creating thoughtful stewardship experiences, and strengthening long-term philanthropic support for Chicago students, this is your opportunity to make an impact. Position Overview The Manager of Annual Giving is responsible for leading Communities In Schools of Chicago's strategy to cultivate, steward, and retain donors. This role combines thoughtful stewardship with a creative, data-informed approach to annual giving-building meaningful relationships while scaling outreach through automation and innovation. The Manager will oversee CIS of Chicago's annual giving programs, including digital and mail campaigns, ensuring a seamless and personalized donor experience at every touchpoint. In addition to managing their own portfolio of annual giving donors, the Manager will collaborate closely with colleagues to design automated workflows, segmented campaigns, and creative content that brings donor impact to life. This role blends strategy and creativity to ensure that every donor feels connected, valued, and inspired to invest in Chicago's students.

Requirements

Bachelor's degree or equivalent experience.
3–5+ years of experience in development, with a focus on donor stewardship, annual giving, or individual fundraising.
Proven success using CRM systems, data segmentation, or marketing automation to enhance donor communication and retention.
Strong writing, creative, and analytical skills; ability to craft compelling donor messages and evaluate campaign performance.
Experience creating and executing multi-channel annual fundraising campaigns.
Strong writing, communication, and relationship-building skills, with an ability to convey impact and gratitude clearly and authentically.
Excellent organizational skills and attention to detail; ability to manage multiple priorities and deadlines.
Passion for education equity and CIS of Chicago's mission.

Nice To Haves

Familiarity with donor databases (e.g., Virtuous, Salesforce, Raiser's Edge) preferred.

Responsibilities

Lead the development and execution of CIS of Chicago's annual giving campaigns from individuals, with an emphasis on data-driven segmentation and automated outreach.
Identify, cultivate, solicit and steward a small portfolio of annual donors who have the capacity to give up to $99,999 annually.
Partner with the major gifts team to identify annual donors who have the capacity to give a major gift of $50,000+ (with a focus on $100,000+).
Develop and implement a comprehensive stewardship strategy for all donors within the annual giving program.
Design and implement creative strategies to grow and retain the donor base, including recurring giving programs, investor calls, and digital engagement initiatives.
Utilize technology and CRM tools to streamline donor communication, track engagement, and deliver personalized stewardship at scale.
Partner with CIS' Associate Director of Communications to craft donor-centered communications, appeals, and storytelling that highlight the impact of CIS of Chicago's mission.
Analyze campaign performance and donor trends to continuously refine and enhance annual giving efforts.
Lead the development of a comprehensive stewardship program that ensures donors at all levels feel appreciated, informed, and connected to the organization's impact.
Create automated and manual stewardship touchpoints, including thank-you messages, impact updates, and recognition moments, tailored to donor segments.
Collaborate with program and communications staff to capture stories, visuals, and outcomes that illustrate the real-world difference donor support makes.
Coordinate with the broader Development team to ensure alignment between annual giving, events, and major gifts for a seamless donor experience.
Work closely with Development and Communications colleagues to integrate technology, creativity, and storytelling into donor engagement strategies.
Represent CIS of Chicago at donor events, school visits, and community gatherings to deepen relationships and highlight mission impact.
Contribute to a culture of philanthropy that values stewardship, innovation, and collaboration.