This senior leadership role oversees all core operational systems for City Year Milwaukee, ensuring that infrastructure, financial operations, facilities, talent acquisition, technology, and cross-departmental workflows are efficient, compliant, and aligned with organizational goals. Reporting to the Senior Managing Director of Program and Operations, the Director acts as a key operational partner, translating policy into site-level guidance, anticipating risks, and managing high-stakes projects.
Responsibilities
Lead the strategy and day-to-day management of City Year Milwaukee's office and training spaces, maintaining high standards of integrity, safety, functionality, and readiness
Manage relationships with property management and third-party contractors, oversee building expenses, conduct routine facility reviews, and resolve maintenance concerns and operational risks promptly
Lead major office transitions and relocation projects, including space planning, vendor coordination, technology and equipment moves, staff communications, timeline management, building access, and operational continuity
Serve as the site operational lead for lease-management support and coordination with building management, engineers, cleaning staff, and other facility partners
Manage the site talent acquisition process in partnership with the Senior Managing Director of Program and Operations and hiring managers, from job posting and candidate sourcing through screening, interviews, selection, reference checks, offer stages, and handoff to onboarding
Establish and maintain consistent hiring workflows, candidate trackers, interview materials, selection documentation, scheduling systems, and communications that support an equitable, timely, and high-quality candidate experience
Advise hiring managers on process, policy, documentation, and timelines; monitor hiring progress and identify barriers or risks that could delay critical staffing needs
Manage the site's annual operating budget and ongoing budget tracking across departments; maintain accurate forecasts, monitor spending, identify variances, and provide regular budget updates and recommendations
Own the district and partner billing process, including preparing billing documentation, validating service and financial data, coordinating submissions, tracking receivables, reconciling discrepancies, and maintaining complete audit-ready records
Lead routine auditing and quality-control processes for district billing, purchasing, invoices, vendor payments, reimbursements, and other financial transactions to ensure accuracy, completeness, policy compliance, and timely resolution of discrepancies
Oversee site purchasing systems and finance workflows; interpret and socialize finance policies; establish internal controls and record-keeping standards; support PCard holders and budget owners; and ensure invoices, contracts, purchase requests, travel needs, and reimbursements are processed accurately and on time
Millions of jobs, with real people getting hired every day
200,000+
New jobs added daily
7,000,000+
Verified job listings
1,000,000+
Tailored applications submitted
Partner with HQ and the Senior Managing Director of Program and Operations to define platform use, administer site systems, resolve technology and workflow challenges, and develop sustainable processes for information management
Manage CyConnect and other site platforms across departments, including resource organization, privacy settings, access, troubleshooting, and coordination with HQ IT
Maintain the MKE Site Calendar and support site technology and equipment management
Read, interpret, and operationalize organizational policies, contracts, procedures, and compliance requirements
Build clear site guidance, controls, tools, and communication processes so staff understand expectations and systems are implemented consistently
Provide strategic oversight of the site uniform fulfillment process for staff and AmeriCorps members, ensuring accurate inventory, ordering, distribution, returns, issue resolution, and cross-departmental communication
Oversee AmeriCorps onboarding and offboarding operational processes related to site and national benefits, ensuring members receive accurate information, enrollment support, and timely escalation of complex issues
Ensure corps-facing operational systems—including benefits support, technology, transportation/parking resources, and other site services—are reliable, well-documented, and coordinated with Impact leadership and HQ partners
Serve as a member of the site's operational leadership structure and provide strategic counsel on organizational risk, process improvement, budget stewardship, staffing operations, facilities, and systems effectiveness
Lead or oversee site retreats, internal special events, operational planning cycles, and major cross-functional projects requiring detailed project management, vendor coordination, budget oversight, and staff communication
Partner across Impact, Development, and People & Operations to improve systems, clarify ownership, strengthen accountability, and ensure operational workstreams support site goals
Develop dashboards, trackers, standard operating procedures, and other tools that improve visibility and execution
Requirements
Bachelor's degree or equivalent combination of education and relevant professional experience
5+ years of progressively responsible experience in operations, finance administration, office/facilities management, talent acquisition, project management, or a related field, including experience owning complex processes from planning through execution
Demonstrated experience leading multiple concurrent projects with competing deadlines, cross-functional stakeholders, shifting priorities, and significant organizational impact
Strong financial management experience, including organizational budget development and tracking, district or partner billing, invoice processing, reconciliation, auditing, purchasing controls, and financial record keeping with a high degree of accuracy
Proficiency with Microsoft 365 (Outlook, Teams, Word, Excel, PowerPoint, SharePoint) and demonstrated ability to learn, administer, and improve business systems and platforms
Excellent written and verbal communication skills, with demonstrated ability to read, interpret, operationalize, and communicate organizational policies, contracts, procedures, and financial requirements to staff and leaders
Ability to physically support facilities work, including moving event walls and lifting or organizing uniform shipments up to 30 lbs.
Commitment to City Year's mission, values, and culturally responsive practices
Nice to have:
Prior City Year, AmeriCorps, nonprofit, education, public-sector, or mission-driven organizational experience
Experience managing end-to-end talent acquisition processes, including posting, screening, interviewing, candidate selection, and offer stages
Experience managing district, government, grant-funded, or partner billing processes and preparing documentation for financial or compliance audits
Experience leading office relocation, facilities transitions, commercial lease coordination, and vendor relationships
Experience owning organizational or departmental budgets, financial forecasting, expense controls, and executive-level reporting
Advanced proficiency with Microsoft 365, particularly Excel for budget tracking, reconciliation, audit support, and operational analysis; strong working knowledge of Outlook, Teams, Word, PowerPoint, and SharePoint
Strong systems-management skills, including the ability to administer platforms, troubleshoot issues, establish workflows, document procedures, and partner effectively with IT and HQ teams
Demonstrated financial acumen across budget management, district/partner billing, auditing, purchasing, invoice processing, reconciliation, forecasting, and internal controls
Demonstrated ability to read and interpret policies, contracts, procedures, and compliance requirements and translate them into practical guidance, tools, and site-level operating practices
Benefits
Health insurance with a Flexible Spending Account
Paid vacation
Holidays
Parental leave
401(k)
Medical, dental, vision, life, accidental death and dismemberment and disability coverage
Flexible Spending Accounts (FSA)
Application Process
Submit your online application
Attach a resume and thoughtful cover letter on the "My Experience" page in the "Resume/CV" field
Important Details
Number of Positions: 1
About the Company
City Year is a mission-driven organization.
City Year helps students and schools succeed, while preparing the next generation of leaders.
