City Year

City Year

Chief Of Staff

Milwaukee, WI
Jul 15, 2022
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Reporting to the Executive Director/Senior Vice-President of City Year Milwaukee, the Chief of Staff oversees the activities of the Executive Office, administrative operations, and human potential operations and systems, and advances City Year Milwaukee’s agenda. The selected candidate will assist the Executive Director with strategic priorities and prioritize and monitor tasks related to the execution and implementation of a broad agenda. They approach the work with a cross-functional (department, organization, and community) mindset and will assume primary responsibility for selecting projects and initiatives as directed.

The CoS serves as a trusted senior advisor to the Executive Director and acts in their place, as appropriate, including representing them in high level meetings and discussions. The Chief of Staff 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.

The CoS oversees a wide range of operations at the site including human resources, finance, office operations and internal communication. The CoS Staff is supported by the Senior Operations Manager, Data Analytics and Corps Experience Manager who directly reports to the Chief of Staff.

The target start date for this position is August 22nd, 2022.


Site Strategy and Special Initiatives (30%)

  • Serve as thought-partner and strategist adviser to the ED, standing in on meetings, challenging ideas, offering a different perspective, and following up on actions steps with the team accordingly.
  • Conduct research, presentation and talking points for the Executive Director on an array of topics and for a breadth of constituencies (when applicable) connected to site strategy.
  • Provide analysis, recommendation, and options to the ED regarding high impact decisions.
  • Track high priority initiatives for the Executive Director to identify any/potential obstacles, provide actionable recommendations and ensure outcomes are achieved.
  • Foster collaboration at the site level by developing agendas, meeting cadence, as well as the scope and sequence for Site Leadership Team (SLT), Directors, Staff and Village meetings.
  • Lead, manage, support, and monitor the development and implementation of City Year Milwaukee’s site advancement plan (SAP) to ensure departmental, individual, and site-wide goals are met through the application of continuous improvement principles while ensuring the plan remains aligned with staff capacity, financial resources, and stakeholder support.
  • Lead in collaboration with the data analytics manager the quarterly review of site and programmatic data to identify successes and gaps to respond to plans to redeploy resources, develop training, and build capacity through an asset-based lens.
  • Champion City Milwaukee Year efforts to be an anti-racist organization through the building and maintaining of an inclusive and diverse workplace by supporting ED in the development and implementation of site vision for DBEI to drive change, working with DBEI committee to create an environment that enables high-performing and inclusive team members to bring their authentic selves to CY MKE and advance in CY, serve as member of City Year Inc. DBEI team.

Human Resources and Site Operations Management (25%)

  • Identify, develop, and direct all human resources management systems and activities for City Year Milwaukee to maximize their strategic use including but not limited to: effective talent acquisition and on-boarding processes, ensuring fidelity of use of PMR system, design and delivery of development programming aligned with site’s strategic talent need to ensure managers can assist employees to be successful, implementation of employee relations programs to foster strong site culture and promote a high level of employee morale, productivity, engagement and retention, etc.
  • Serve as the key human resources subject matter expert, coach and site strategic planner and consultant, promoting site and org. wide initiatives, advising site directors and senior staff on best practices, and providing tools and guidance for effective management.
  • 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.
  • Establishes and maintains collaborative relationships internally and externally to maximize human resource contributions and attain critical strategic priorities.
  • Understand and communicate City Year policies and procedures on behalf of City Year Milwaukee and in consultation with City Year Inc. necessary to ensure appropriate equitable decision-making protocols are followed.
  • Develop, formulate, and interpret personnel policies and procedures providing staff guidance, instruction, and interpretation for application.
  • Develop, coordinate, implement and monitor participation in site wide committees that support City Year Milwaukee.
  • Supervise the director of people, senior manager of operations, and data analytic manager and director of people in the day-to-day execution of their duties and provide ongoing support, guidance, development, and feedback to ensure their success as a team member and professional.
  • Work on the behalf of the Executive Director for critical staff position searches.
  • Consult with Executive Director and Headquarters staff to ensure effective HR and site operations management.

Budget Development and Financial Monitoring (15%)

  • Organize and support the site in the annual budget development process in consultation with the Executive Director and Headquarters staff.
  • Support development where necessary to analyze financial statements and revenue projections.
  • Monitor site’s financial progress and make recommendations to the Executive Director and department heads as appropriate.
  • 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 site operation planning, staff reviews, and provide training and support to department finance managers as needed.

Board and Internal Communication Support (10%)

  • In collaboration with the Director of Communication, 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.
  • With the support of the Senior Operations Manager, build and execute an internal communications strategy for City Year Milwaukee including regular staff and AmeriCorps members newsletters.
  • Serve as the staff point for the board nomination committee and assist other committees with special projects by conducting research, collecting, and analyzing data, drafting reports, and preparing presentations for internal and external stakeholders.
  • Create board pre-read documents, presentations, and collateral materials for site board quarterly meetings focused on human resources, finance, and operations.
  • Support the media and messaging needs of crisis management for the site.

Americorps Policy Work (10%)

  • In collaboration with the ED establish and maintain relationships with local and state policy makers.
  • On behalf of the office of the ED work directly with lobbyists to promote City Year Milwaukee and other Americorps serving organizations.
  • Serve as convener of local Americorps serving organizations to collaborative build out policy agenda.

Organization Initiatives (5%)

  • Serve a member of SLT, providing strategic insights and leadership.
  • Work collaboratives with COS from other City Site sites, HQ People team on a frequent basis.
  • Partner on cross-department projects and initiatives including but not limited to the AmeriCorps member selection process, stakeholder engagement, service day participation and cross-departmental committees as needed to ensure site-wide goals are met.
  • Attend and help for whole site events including Opening Day, MLK Day, Global Youth Service Day, Annual Dinner, Graduation, and other site-wide designated events.
  • Attend an overnight and other national events to represent the site (when applicable).
  • Participate in City Year Milwaukee portfolio groups on topics of interest.
  • Assume other tasks as delegated by the ED.

Basic Qualifications

  • A background in Business, Public Policy or Non-Profit Management is very strongly preferred
  • Minimum of 5 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 conducting conflict resolution, coaching, and group facilitation exercises
  • Leadership, influencing and negotiation skills a must
  • Experience leading HR systems and processes strongly preferred
  • Deep understanding of City Year’s mission and core values

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.
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