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Controller - Chicago - Aigentless
Description
Position: Controller
Reports to: Head of Operations
Location: Chicago, IL OR New York City (NYC)
Type: Full-time | In-office
The Company
Aigentless is a fast-growing proptech software company redefining the residential leasing experience through automation and AI. Trusted by some of the largest real estate operators in the country, our platform enables property teams to deliver seamless, self-guided tours while improving operational efficiency across their portfolios.
As we continue to scale, we are building the operational and financial infrastructure to support growth — creating opportunities for high-impact team members who want ownership in a fast-moving startup environment.
The Role
We are seeking a hands-on Controller to lead the day-to-day financial operations of a growing startup. This role is ideal for someone who enjoys owning the details, creating financial clarity, and ensuring strong financial discipline across accounting, contracts, receivables/payables, and reporting.
You will work closely with leadership to deliver accurate financial visibility and scalable processes that support the company's continued growth.
Key Responsibilities
Financial Operations & Reporting
· Own the monthly close process and preparation of financial statements
· Produce accurate income statements and management reporting
· Maintain financial records, reconciliations, and internal controls
· Support budgeting, forecasting, and financial analysis
Contracts & Revenue Administration
· Manage financial components of client contracts and SOWs
· Ensure billing accuracy and alignment with contract terms
· Oversee invoicing workflows within the ERP system (Rillet)
· Manage manual billing processes where required
Accounts Receivable & Payable
· Oversee AR/AP processes to ensure timely billing and collections
· Monitor cash flow and payment cycles
· Maintain vendor relationships and payment controls
Systems & Process Ownership
· Maintain and optimize accounting workflows within Rillet ERP
· Improve financial processes and automation as the company scales
· Partner with leadership to implement operational best practices
Qualifications
· years of accounting or finance experience, ideally in startup or high-growth environments
· Strong understanding of financial reporting and income statement management
· Experience managing AR/AP and contract-driven billing processes
· ERP experience required (Rillet experience a plus)
· Experience in a SaaS (Software-as-a-Service) or recurring revenue business model preferred
· Highly organized with strong attention to detail
· Comfortable working independently in a fast-paced environment
· CPA or accounting degree preferred
What Success Looks Like
· Clean, reliable monthly financial reporting
· Accurate contract-to-billing execution
· Efficient AR/AP workflows
· Strong financial visibility for leadership decision-making
· Scalable accounting processes that support company growth
Employee Benefits
Employment Contingencies
Aigentless is an Equal Opportunity Employer—we do not discriminate based on race, religion, sex, national origin, age, disability, veteran status, sexual orientation, gender identity, or any other legally protected characteristic.
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