Accounting Manager, Revenue and Billing

The Accounting Manager, Revenue & Billing, leads a small, distributed team responsible for multi-entity billing, invoicing, cash reconciliation, and revenue/commission close processes. This role owns billing decisions tied to contract terms, overseeing the full invoice lifecycle, and partners closely with the AP Manager and broader finance team on cash reporting, month-end close, and budgeting. Success in this role requires strong leadership across onshore and offshore staff, sound judgment on contract-driven billing questions, and the ability to keep a high-variability workload organized and on schedule.
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Key ResponsibilitiesTeam LeadershipManage, coach, and hold accountable a team of three direct reports: a Senior Accountant (offshore), a Bookkeeper (offshore), and a Collections Manager (onsite). Train and onboard new team members.Maintain SOPs for billing, invoicing, and collections; identify opportunities to automate or streamline processes.Billing & Contract ComplianceOwn billing decisions based on contractual terms, coordinating with the Senior Accountant on setup during client onboarding and on changes to existing contracts.Oversee billing for offboarding clients, including coordinating team efforts to calculate and bill prorated fees.Oversee commission and fee calculation.AR Management & Write-Off AuthorityReview AR aging, approve credit memos and bad-debt write-offs, and set escalation thresholds for the Collections Specialist.Invoicing OversightEnsure all invoices are distributed correctly, right method, right recipient, by directing and coordinating the team's efforts across a high-variability client environment.Cash & ReportingPerform bank-to-book cash review and produce weekly cash reporting in collaboration with the AP Manager.Month-End Close & BudgetingCoordinate month-end close activities and reporting related to revenue and commission items.Assist with the budget process for revenue and commission line items. xzbcwsv Workflow ManagementMonitor shared department inboxes, assign responsibility for incoming items, and follow up to ensure timely completion.Systems UsedQuickBooks OnlineRampGoogle WorkspaceMS OfficeRequired Experience & SkillsBachelor’s degree in accounting, Finance, or a related field, or equivalent experience5+ years of progressive accounting experience2 years directly managing or supervising staffDemonstrated experience managing remote or offshore team membersExperience with contract-based billing, including handling contract changes and client offboarding/prorationHands-on month-end close experience, ideally with exposure to revenue and commission accountingExperience with bank reconciliation and cash reportingProficiency with QuickBooks Online; advanced Excel skills (pivot tables, lookups, reconciliation workbooks)Strong organizational and prioritization skills; comfortable managing shifting priorities and a high-variability workloadClear, proactive communicator able to collaborate cross-functionally (e.g., with an AP Manager)PreferredKnowledge of multifamily real estate concepts & operationsPrior experience overseeing or working closely with a Collections functionFamiliarity with commission plan structures and calculationsExperience in a professional services, subscription, or contract-driven revenue environmentDirect reports (3): Senior Accountant (offshore), Bookkeeper (offshore), Collections ManagerLocation: Chicago, IL Hybrid More information: Cross Street Real Estate LLC - Accounting Manager, Revenue and Billing