Senior Director, Development

Application Instructions

Click Apply to submit your online application. Please attach a resume and thoughtful cover letter on the "My Experience" page in the "Resume/CV" field.

Active City Year Staff members must login to Workday to apply internally.

Number of Positions: 1
Compensation: $90,000.00 - $ 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…