Strategic Billing & Revenue Manager (Hybrid)

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

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.