Reporting to the Executive Director of City Year Milwaukee, the Chief of Staff oversees the activities of the Executive Office, administrative operations and the operations departments of the site, and advances City Year Milwaukee’s Long Term Impact goal. The selected candidate will assist the Executive Director with strategic priorities, and prioritize and monitor tasks related to the execution and implementation of new systems to sustain growth. He/she will approach the work with a cross-functional (department, organization, and community) mindset and will assume primary responsibility for select projects and initiatives as directed.

The Chief of Staff serves as a trusted senior advisor to the Executive Director and acts in his place, as appropriate, including representing them in high level meetings and discussions. He/she will provide oversight on time sensitive issues and initiatives that include cross-functional, organizational, and community dimensions. They are also responsible for building and sustaining an effective support structure for the site’s senior leadership team.

Site Strategy and Special Initiatives

• Manage the implementation, review, and modification of City Year Milwaukee’s strategic long term impact plan to ensure that departmental and site-wide progress is met and remains aligned with staff capacity, financial resources, and stakeholder support.
• Support the development/execution of City Year Milwaukee’s High Priority Goals and assist departments with the development of their annual operation plans.
• Support departments and senior staff in the establishment of strategic and sustainable long-term partnerships with public and private organizations.
• Monitor departmental and individual progress towards annual goals, recommend action, and advise Executive Director concerning interventions as necessary.
• Work with team to conduct research, prepare speeches, presentations, and talking points for the Executive Director on an array of topics and for a breadth of constituencies.
• Work on the behalf of Executive Director for critical staff positions searches and other site needs.

City Year Milwaukee Board

• Oversees coordination of meetings, retreats, and communications to City Year Milwaukee Board.
• Assist committees with special projects by conducting research, collecting and analyzing data, drafting reports, and preparing presentations for internal and external stakeholders.
• Manage a Board member committee.
• Serve as staff liaison in supporting the board, development team and other staff board relationship managers to increase communication and efficiency.

Budget Development and Financial Monitoring

• Organize and support the site in the annual budget development process in consultation with Executive Director and Department Directors.
• Support development where necessary to analyze financial statements and revenue projections.
• Monitor site’s financial progress and make recommendations to Executive Director as appropriate, with support from the Operations Coordinator.
• Collaborate with the financial analyst and development team to identify cost savings and revenue generation opportunities, prepare program budgets, and align operating budgets with strategy and donor intent.
• Lead the site through operation planning such as staff reviews, staff planning, staff development, site expansion, etc. 

Executive Office Management and Site Operations

• Prioritize agenda and schedule of the Executive Director and manage work flow of the Executive Office and Senior Leadership Team.
• Supervise Executive Office team (Operations Coordinator, Special Projects Manager, Communications and Brand Manager) and contribute to their development as a skilled professional.
• Write and review correspondence on behalf of the Executive Director to ensure communication is accurate, timely, and coordinated with other City Year Milwaukee and City Year Inc. initiatives.
• Anticipate the needs of the Executive Director and Senior Leadership Team in order to ensure efficiency and effectiveness.
• Foster productive and collaborative relationships internally and externally on behalf of the Executive Director and Department Directors.
• Establish and communicate site-wide processes and policies on behalf of City Year Milwaukee and in consultation with City Year Inc.
• Respond to and meet with a broad range of internal and external individuals, frequently related to matters of immediate concern, and coordinate responses, solutions and follow-up.
• Understand City Year policies and procedures necessary to ensure that appropriate decision-making protocols are followed.

Participate in Organizational Initiatives

• Attend and help mobilize your team(s) for whole site events like Opening Day, Make A Difference Day, MLK Day, National Youth Service Day, Annual Gala, Graduation and other site-wide designated events.
• Attend overnight events including BTR, ATR, Academy (a conference for all City Year Staff held in Boston in July) and other national events.

• College degree required, advanced degree preferred.
• Minimum of 4 years of experience successfully leading cross-functional teams.
• Demonstrated ability to lead directors and managers in the creation and implementation of multi-faceted operating plans and budgets.
• Experience developing new programmatic and financial partnerships with community-based organizations, corporations, and civic leaders.
• Strong project management and organizational skills, and the ability to manage multiple priorities in a complex environment.
• Excellent analytical, verbal and written communication skills along with a high level of diplomacy, discretion and problem solving ability.
• Proven success in developing collaborative relationships, and a successful track record of providing successful advice and counsel to senior leaders.
• Experience in conducting conflict resolution, coaching, and group facilitation exercises.
• Leadership and negotiation skills a must.
• Deep understanding of City Year’s mission and core values.

Compensation and Benefits

Compensation commensurate with experience. Great benefits including health insurance with Flexible Spending Account, paid vacation, holidays, parental leave, 401K, and more.