Number of Positions: 1

Compensation: $90,000.00 – $100,000.00 Annually Commensurate with Experience and Location

Position Overview

City Year Chicago is seeking a dynamic Senior Director of Development who will lead efforts to secure financial support from individuals in the metro Chicago area. Reporting to the Managing Director of Development and working closely with other members of the development team, senior leaders, volunteers, and board members, the Senior Director of Development is responsible for meeting quarterly and annual goals by identifying, cultivating, soliciting, and stewarding a diverse base of individual donors.

This position will play a critical role by assisting the Managing Director of Development in the successful execution of a substantial and sustainable individual giving program, the Red Jacket Society, and the execution of our primary fundraising event, Ripples of Hope. This individual will work in close partnership with other members of the Development team. The Senior Director of Development will also work closely with City Year Chicago’s Marketing & Communications team to fully leverage the site’s outreach activities and events to meaningfully engage prospective and current donors and alumni. The Development Department is responsible for securing more than $3.5M in annual support from individual, corporate, and foundation sources.

Job Description

Responsibilities

Fundraising and Donor Acquisition Strategy

Oversee a portfolio of 125 individuals to meet a $750,000 personal fundraising goal by securing $250,000 or more in new or increased donations within 12 months.

Renew at least 85% of the current donors in your pipeline.

Work closely with the Development team and Site Board to build a prospect portfolio and ensure the flow of prospects into the giving pipeline, from identification through stewardship.

Serve as owner of our annual Ripples of Hope Gala (500-person seated dinner) and support the efforts of our board to identify and solicit prospects to sponsor and attend the event.

Develop strategies to identify, cultivate, and solicit $10,000+ annual support and multi-year commitments from new donors by building a robust Red Jacket Society.

Strategy & Revenue Leadership – Individual Giving

Own and lead the strategic vision for individual giving at City Year Chicago, including goal-setting, donor segmentation, pipeline development, and multi-year growth planning.

Partner with the Managing Director of Development and other senior leaders to align individual giving strategies with overall site priorities and revenue targets.

Leverage data and donor insights to inform personalized engagement plans, stewardship strategies, and donor retention efforts across giving levels.

Build and expand the Red Jacket Society by creating a scalable plan to attract, upgrade, and retain $10,000+ annual donors.

Develop and implement moves management strategies for key prospects and donors, including targeted cultivation touchpoints, personalized stewardship, and strategic use of events and volunteer opportunities.

Regularly assess the performance of individual giving efforts, using metrics and qualitative feedback to refine approach and maximize ROI.

Cultivation and Stewardship

Ensure the successful stewardship of current Red Jacket Society members by managing appropriate frequency of outreach, communication, appreciation and involvement.

Work with staff and key stakeholders to develop, execute and evaluate strategies to engage Red Jacket Society members through outreach, education, and invitations to special events.

Collaborate with the Marketing and Communications department to create and implement communications and acknowledgement related to cultivation and stewardship of grants and foundation partners.

Development Operations

Work with the Senior Manager of Development Operations to ensure accurate tracking and reporting of institutional gifts and engagement using City Year’s Salesforce CRM.

Partner with the Senior Manager of Development Operations and other team members to hold regular prospecting, pipeline, revenue forecasting, and moves management meetings.

Work closely with fellow Development team members to understand priorities and business goals and develop strategies to meet the organization’s needs.

Work with the development team to leverage events to increase giving, such as City Year’s Ripples of Hope fundraiser, service days (school beautification projects), and school visits for potential donors.

Represent City Year at external and partner functions to establish and deepen potential and current donor relationships.

Qualifications

Communication: clearly articulates information and ideas verbally and in writing; inspires diverse audiences through compelling, tailored messaging; communicates with confidence and credibility; listens carefully and is responsive to feedback

Relationship Development: Establishes and builds diverse, mutually beneficial, and sustainable partnerships within City Year Chicago.

Team Collaboration & Leadership: Leverages diverse strengths of team members to achieve desired results; coaches and empowers others to lead; addresses and resolves team conflicts swiftly and effectively

Requirements

Bachelor’s degree preferred; seven or more years of relevant work experience including knowledge of fundraising for non-profit or educational organization preferred.

Strong knowledge base of all aspects of fundraising with a strong emphasis on individual giving programs.

Proven ability to lead and motivate a diverse team of volunteers to meet fundraising goals.

Experience using donor/relationship management software to track donors, establish goals, and generate reports (experience with Salesforce preferred).

Exceptional verbal and written communication skills with an ability to engage and inspire a wide range of audiences.

Excellent organizational skills, ability to handle multiple tasks and think critically.

Passion for and understanding of City Year’s work within the national service movement and education sphere.

Proficiency with Microsoft Office platforms required.

City Year and AmeriCorps alumni are encouraged to apply.

Required Documents

A cover letter and resume must be submitted to be considered for this position. Preferred resume formats will depict not only a candidate’s responsibilities and job functions in previous work, but will include specific, quantitative results where applicable. Additional quantitative context around specific budget sizes, team sizes, or other work environment information will help City Year compare the scale of your work environment with our operations

Benefits

Full-time employees will be eligible for all benefits including vacation, sick days and organization holidays. You may participate in all benefit programs that City Year establishes and makes available to eligible employees, under (and subject to all provisions of) the plan documents that govern those programs. Currently, City Year offers medical, dental, vision, life, accidental death and dismemberment and disability coverage, Flexible Spending Accounts (FSA), and other benefits including 401(k) plan(s) pursuant to the terms and conditions of company policy and the 401(k) plan document. For more information, click here.

Employment at City Year is at-will.

City Year does not sponsor work authorization visas.

Senior Director of Development

Job Type