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Financial Controller

Job in Chicago, Cook County, Illinois, 60290, USA
Listing for: Trolley AI
Full Time position
Listed on 2026-07-08
Job specializations:
  • Accounting
    Financial Compliance, Financial Controller, Financial Reporting, Payroll
Job Description & How to Apply Below

Financial Controller | Full-Time | PST or EST Time Zones

Location:

Remote

Type:
Full-Time Contractor

Hours:

40 hours/week

Reports To:

CEO (Moj Mahdara)

Who We're Looking For

We're looking for a highly organized, operationally strong Financial Controller who can oversee multi-entity financial operations with precision, accountability, and zero tolerance for errors. This is not a basic bookkeeping role. The Financial Controller acts as the operational backbone of the finance function — ensuring all entities remain reconciled, compliant, audit-ready, and financially organized at all times. The ideal candidate is proactive, detail-oriented, systems-minded, and capable of independently managing AP, reconciliations, payroll, compliance, banking, and reporting across multiple entities without constant oversight.

You should thrive in high-accountability environments, communicate proactively, and understand how to maintain financial hygiene inside fast-moving companies.

What You'll Own
  • Oversee weekly and monthly close processes across multiple entities
  • Maintain fully reconciled financials with zero uncategorized balances
  • Manage AP workflows, vendor payments, W-9/1099 documentation, and approval tracking
  • Monitor cash flow, account balances, and tax reserve schedules proactively
  • Manage payroll processing and reconciliation through Deel
  • Maintain organized, audit-ready financial records and data rooms
  • Coordinate with CPAs, legal teams, FP&A, and leadership across reporting and compliance workflows
  • Support automation of reconciliation and reporting systems using available integrations and tools
  • Maintain budget-to-actuals tracking and flag anomalies or risks proactively
  • Ensure compliance, filing deadlines, and internal financial controls remain current and organized
Workflow & Collaboration
  • Work directly with the CEO, FP&A, Senior Bookkeeper, CPAs, and legal partners
  • Maintain finance visibility and workflow tracking inside Click Up
  • Deliver structured financial updates proactively without requiring follow-up
  • Escalate risks, missing approvals, or operational blockers early
  • Support cross-functional operational and strategic finance discussions when needed
What We Need From You
  • Experience managing multi-entity financial operations, reconciliations, and close processes
  • Strong understanding of U.S. GAAP, AP/AR workflows, compliance, and audit readiness
  • Experience with Quick Books Online, Deel, Click Up, and modern finance operations tools
  • Strong operational discipline, organization, and documentation management
  • Ability to manage sensitive financial workflows with accuracy and discretion
  • Proactive communication and strong ownership mentality
  • Comfort operating independently in fast-moving environments
  • Experience supporting founders, startups, or high-growth companies is strongly preferred
Who Thrives Here

This role is best suited for someone who:

  • Notices inconsistencies and resolves them quickly
  • Operates with high precision and accountability
  • Thinks in systems, controls, and operational structure
  • Escalates issues before they become problems
  • Maintains calm under pressure and shifting priorities
  • Takes ownership without waiting for reminders or direction
About Us

Trolley is a fast-growing creative operations company delivering high-impact digital and marketing solutions for high-profile clients. We operate with an AI-first, Founder Mode mindset focused on ownership, execution, operational excellence, and continuous improvement.

Benefits
  • Fully remote work
  • Flexible schedule and time off
  • Access to leading AI tools
  • Direct collaboration with leadership
  • Long-term career growth opportunities
  • High-trust, fast-moving team culture
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