Operations Director

City Year•Milwaukee, WI

43d•$60,000 - $65,000•Onsite

About The Position

The Operations Director is a senior site leader responsible for the strategic oversight, execution, and continuous improvement of City Year Milwaukee's core operational systems. The Director ensures the site's infrastructure, financial operations, facilities, talent acquisition processes, technology systems, and cross-departmental workflows are effective, compliant, and aligned to organizational priorities. Reports to: Senior Managing Director of Program and Operations. Reporting to the Senior Managing Director of Program and Operations, the Operations Director serves as a key operational partner and connector across Impact, Development, and People & Operations. This role translates organizational policy into clear site-level systems and guidance, anticipates operational risks, manages high-stakes projects and transitions, and ensures leaders have accurate information to make sound decisions.

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 Haves

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.

Responsibilities

Lead the strategy and day-to-day management of City Year Milwaukee's office and training spaces, maintaining a high standard of facility integrity, safety, functionality, and readiness.
Manage relationships with property management and third-party contractors; oversee building supply and maintenance expenses; conduct routine facility reviews; and ensure maintenance concerns and operational risks are resolved 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 before, during, and after a move.
Serve as the site operational lead for lease-management support and coordination with building management, engineers, cleaning staff, and other facility partners. Ensure meeting, event, parking, technology, and workspace needs are effectively supported.
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 to the Senior Managing Director of Program and Operations.
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.
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 to the Senior Managing Director of Program and Operations 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.