Website City Year

Number of Positions: 1

Work Location: 100% On-Site


Position Overview

City Year Chicago is seeking a skilled fundraising professional with an entrepreneurial mindset to be the Managing Director of Development. The ideal candidate is an ambitious and sophisticated forward-thinker, communicator, and equity-driven fundraising professional who thrives in roles that require them to be strategic, creative, and collaborative.

Reporting to the Executive Director, as a member of the site’s Executive Leadership Team, the Managing Director of Development (MDD) will lead a team of 5 development professionals to manage and implement the fundraising strategy for the Chicago office. This person is responsible for developing and implementing the Development strategy for City Year Chicago to raise and sustain at least $3.75M from the private sector in FY25 and grow annually. The MDD will develop and execute strategic, diversified development plans to raise funds through grant writing, individual giving, and institutional partners, such as corporations and foundations. A focus on establishing multi-year contributions, identifying new funding sources and management of ongoing donors will be expected.

The ideal candidate is an initiative-taking problem-solver and strategic thinker who is committed to helping advance educational equity by developing leaders and supporting students in Chicago’s most under-resourced schools.

City Year values and continuously works to build an equitable and inclusive culture where people with diverse lived experiences feel they belong.

The salary range for this role is $135K – $163K annually, commensurate with experience.


Job Description

The Managing Director, Development will focus on establishing multi-year contributions, identifying new funding sources and management of current donors. The Managing Director, Development (MDD) will oversee a team that will be responsible for achieving the site’s fundraising goals including major gift solicitation, grant writing, event planning, as well as the site’s external communications and marketing efforts. The MDD will serve on the site leadership team, helping to drive and support site-wide initiatives and projects.


Fundraising Strategy:
In partnership with the Executive Director and the City Year Chicago’s Board and Development team, leverage and enhance the site’s existing Development plan to implement a strategic and diversified fundraising plan that meets the current goal of raising $3.75M from the private sector and anticipates future needs and growth objectives.
In partnership with the Executive Director, Develop, implement and monitor progress toward short- and long-term fundraising strategy and goals.
Develop strategies to identify and secure partnerships with corporations and foundations that reflect their marketing and business needs as well as philanthropic and community engagement goals.
Create strategies to identify and secure new individual supporters, fully leverage existing relationships, increase multi-year commitments, and maintain or elevate current commitments.
Implement a high-quality stewardship program that engages, recognizes, and thanks supporters to strengthen their relationship with the organization.

People Management & Team Leadership:
Hire, lead, and retain a team of 5 development professionals.
Directly supervise the Director of Corporate Partnerships, Director of Individual Giving, Director of Foundations and Grants, and the Development Operations Manager. Support ongoing coaching, career growth, and professional development for a diverse staff.
Relationship Cultivation and Fundraising Management:
Build meaningful relationships that result in securing both monetary and in-kind multi-year support for City Year Chicago.
Able to grow a transactional relationship into a transformational relationship.
Oversee and support Corporate Partnerships and Major Gifts Development fundraising efforts.
Serve as a public representative of the organization, including cultivating relationships with community members, including prospective gift givers in order to build awareness of and commitment to City Year Chicago’s work.
Maintain oversight over all fundraising activities including major giving, grants, special events, direct mail appeals, corporate partnership initiatives.
Manage relationships and communication with current corporate and foundation funders.
Manages the identification and cultivation of new corporate and foundation partnerships, as well as the grant proposal and reporting processes for corporate, foundation and government funders.
Develop successful identification, cultivation, solicitation and stewardship strategies to direct and monitor the progress of current and future donor relationships.
Ensure diversity and sustainability of site donor base.

Portfolio Management:
Build and manage a portfolio consisting of donors and prospects with $25,000+ capacity for giving, and a focus on prospects capable of giving $100,000+.  Cultivate, solicit, and close annual, major gift and multi-year contributions.
Achieve 75 meaningful contacts with portfolio prospects annually and make 50 intentional asks.
Document and maintain clear and timely records and call reports to track contacts, donor giving, and notes in the Salesforce database.

Board Management and Engagement:
In partnership with the Executive Director, the MDD will engage the Board to meet critical financial and advocacy goals for the organization.
Participate in quarterly Board of Directors meetings and prepare monthly, quarterly and annual reports as requested by the Executive Director and Board.
Serve as primary relationship manager for Development Committee or Development focused board members.
Provide regular updates and maintain engagement (both financially and otherwise) to ensure Board retention and satisfaction.
Oversee the execution and strategy of the associate board and alumni board to support site fundraising efforts and strategic initiatives

Events and Civic Engagement Program Strategy Leadership:
In partnership with site leadership and Development team, drive strategies to leverage large-scale fundraising events, including our annual Ripples of Hope Gala as well as smaller events to thoughtfully engage donor communities.
Partner with the Managing Director of Partnerships and Civic Engagement to drive the strategy around how to leverage our Civic Engagement efforts to create fundraising and service opportunities for corporate partnerships and individual donors.

Marketing and Communications:
Experience crafting communication on behalf of others with keen awareness of audience and impact.
Ability to manage and execute compelling communication tools that drive people to support and champion City Year Chicago, including press releases, media advisories, social media communication and marketing events.
Experience communicating with both internal and external audiences of varying levels of seniority.

Development Operations:
In partnership with the Development Operations staff, support development business processes from donor identification through to stewardship, ensuring accurate maintenance of records and donor information in the Salesforce database.
Direct monthly pipeline meetings with the Development team and Executive Director to provide updated revenue figures, pipeline reports, and progress towards monthly/quarterly goals.
Identify areas for operational improvements and drive continual improvements of processes.

Organizational Leadership:
Help shape organizational strategy and play a leadership role in implementing the site’s local operating plan as a member of the Executive Leadership Team.
Work collaboratively with other site departments and City Year’s national and regional staff. Represent, respect, and role-model City Year’s organizational culture and values internally as a member of the site Senior Leadership Team, and externally as a primary representative of the organization.
Actively contribute as leadership team member and support our ongoing Diversity, Equity, Inclusion & Belonging work. Partner with all departments through site events, projects, and cross-departmental committees as needed to ensure site-wide goals are met.

Bachelor’s degree and master’s degree highly preferred
At least 5-7 years of non-profit fundraising experience, gained in a frontline fundraising role.
Direct experience leading Development program, including managing diverse teams.
Proven track record of raising funds from diverse sources, including major gifts from individuals, foundations, corporations
Skilled in working across all levels of employees and stakeholders, including Board members and committees.
Strong interpersonal, networking, and relationship building skills.
Persuasive written and verbal communication skills.
Ability to problem solve, work independently, meet deadlines, and balance multiple high-profile partner priorities simultaneously.
Passion for service, the empowerment of young people, and City Year’s mission to provide educational equity and school success for those who are further from opportunities.
Flexibility to attend in-person donor meetings, work related events, respond to unpredictable partnership needs, and other duties as assigned, which at times are outside of standard working hours.
Experience with navigating a complex political landscape and developing relationships with key stakeholders
Knowledge of high-net-worth and philanthropic community in Chicago via local business, civic, and cultural networks desirable.
City Year/AmeriCorps experience a plus
Experience with Salesforce preferred
Deep understanding of and commitment to City Year’s values, for more information visit:

Key Competencies:
In order to succeed in this role, the applicant must have the following competencies:
External Relationship Development: takes initiative in establishing new partnership and external opportunities; ability to secure new commitments to the organization; strong interpersonal and relationship building skills in one-on-one and large group settings.

Strategic Thinking and Planning: develops and translates strategies into action plans that build the capacity of the site/department; creative out-of-the-box thinker.

Executes to Results: is proactive and a problem-solver, produces high quality work, prioritizes appropriately, and accepts accountability; delegates responsibilities and holds others accountable.

Communication: ability to communicate mission and vision to diverse audiences using creative storytelling to connect to individual/corporate passions and purpose; clearly articulates information and ideas orally and in writing.

Desire to Learn: City Year has a unique service model and organizational culture. Successful applicants will have strong experience and a proven track record of success in the above areas but must also be willing and eager to continue to learn.

Full time employees will be eligible for all benefits including vacation and 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 and vision, life, accidental death and dismemberment and disability coverage, Flexible Spending Accounts (FSA), 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.

COVID-19 Notice

Our number one priority is the health and safety of our employees and AmeriCorps members and their families; our students and school partners; and the community at large from COVID-19. Proof of COVID-19 vaccination is required for employment and service – all staff members, including remote staff, and AmeriCorps members are required to be fully vaccinated* no later than their start date. If you are unable to be vaccinated for medical reasons or sincerely-held religious beliefs, we will consider requests for reasonable accommodation consistent with our policy, and where we are able to provide such accommodations without undue hardship to the organization pursuant to applicable law. Notwithstanding any language herein, City Year will comply with any state, local, or federal orders, statutes, or regulations that may conflict with the COVID-19 vaccination policy.

*Individuals are considered fully vaccinated 14 days after the completion of their primary vaccination series.

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