Accounting Manager, Revenue and Billing

Cross Street; Chicago (IL); Hybrid; USD 90,000 - 130,000; Full time

Job summary

Cross Street Real Estate LLC in Chicago, IL is seeking an Accounting Manager, Revenue and Billing to lead a distributed team responsible for multi-entity billing, invoicing, cash reconciliation, and revenue/commission close processes. The role owns billing decisions tied to contract terms and collaborates with the AP Manager on cash reporting and month-end close.

The ideal candidate will manage a remote/offshore team, maintain SOPs, and oversee prorations and client offboarding.

Qualifications

• Bachelor’s degree in accounting, Finance, or related field, or equivalent experience.
• 5+ years of progressive accounting experience.
• 2 years directly managing or supervising staff.
• Demonstrated experience managing remote or offshore team members.
• Experience with contract-based billing, including handling contract changes and client offboarding/proration.
• Hands-on month-end close experience, ideally with exposure to revenue and commission accounting.
• Experience with bank reconciliation and cash reporting.
• Proficiency with QuickBooks Online; advanced Excel skills (pivot tables, lookups, reconciliation workbooks).
• Strong organizational and prioritization skills; comfortable managing shifting priorities and a high-variability workload.
• Clear, proactive communicator able to collaborate cross-functionally (e.g., with an AP Manager).

Responsibilities

• Lead a small distributed team across onshore and offshore staff.
• Coach and onboard new team members; maintain SOPs for billing, invoicing, and collections.
• Own billing decisions based on contract terms and client onboarding changes.
• Oversee billing for offboarding clients, including prorated fees.
• Oversee commission and fee calculation.
• Review AR aging, approve credit memos and bad-debt write-offs; set escalation thresholds.
• Ensure invoices are distributed correctly to clients.
• Produce weekly cash reporting in collaboration with AP Manager.
• Coordinate month-end close activities and reporting for revenue and commissions.
• Assist with budgeting for revenue and commission line items.
• Monitor shared inboxes and ensure timely task completion.

Skills

Remote team management

Contract-based billing

Month-end close

Bank reconciliation

QuickBooks Online

Excel (Pivot, Lookups)

Cross-functional collaboration

Education

Bachelor's degree in accounting/Finance

Tools

QuickBooks Online

Ramp

Google Workspace

MS Office

Job description

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.

Key Responsibilities

• Manage, 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.
• Own 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 Authority

• Review AR aging, approve credit memos and bad-debt write-offs, and set escalation thresholds for the Collections Specialist.

Invoicing Oversight

• Ensure all invoices are distributed correctly, right method, right recipient, by directing and coordinating the team's efforts across a high-variability client environment.

Cash & Reporting

• Perform bank-to-book cash review and produce weekly cash reporting in collaboration with the AP Manager.

Month-End Close & Budgeting

• Coordinate month-end close activities and reporting related to revenue and commission items.
• Assist with the budget process for revenue and commission line items.

Workflow Management

• Monitor shared department inboxes, assign responsibility for incoming items, and follow up to ensure timely completion.

Systems Used

• QuickBooks Online
• Ramp
• Google Workspace
• MS Office

Required Experience & Skills

• Bachelor's degree in accounting, Finance, or a related field, or equivalent experience
• 5+ years of progressive accounting experience
• 2 years directly managing or supervising staff
• Demonstrated experience managing remote or offshore team members
• Experience with contract-based billing, including handling contract changes and client offboarding/proration
• Hands-on month-end close experience, ideally with exposure to revenue and commission accounting
• Experience with bank reconciliation and cash reporting
• Proficiency with QuickBooks Online; advanced Excel skills (pivot tables, lookups, reconciliation workbooks)
• Strong organizational and prioritization skills; comfortable managing shifting priorities and a high-variability workload
• Clear, proactive communicator able to collaborate cross-functionally (e.g., with an AP Manager)

Preferred

• Knowledge of multifamily real estate concepts & operations
• Prior experience overseeing or working closely with a Collections function
• Familiarity with commission plan structures and calculations
• Experience in a professional services, subscription, or contract-driven revenue environment

Direct reports (3): Senior Accountant (offshore), Bookkeeper (offshore), Collections Manager

Location: Chicago, IL Hybrid

More information: Cross Street Real Estate LLC - Accounting Manager, Revenue and Billing