Accounting Manager, Revenue and Billing in Chicago, Illinois at Cross Street Real Estate LLC

Title: Accounting Manager, Revenue and Billing

Reports to: Financial Controller

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

Location: Chicago, IL Hybrid

Position Summary

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

Team Leadership

• 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.

Billing & Contract Compliance

• 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

What We Offer

• Compensation: $120,000-$130,000 annually
• Comprehensive benefits package including Medical (BCBS), Dental and Vision Insurance
• Eligibility for participation in a 401(k) plan
• Paid time off including vacation and sick days
• 15 Company paid Holidays and your Birthday off
• A collaborative and entrepreneurial culture committed to innovation and career growth.