[Hiring] Financial Controller @Trolley

Role Description

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 ClickUp
• 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

Qualifications

• 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 QuickBooks Online, Deel, ClickUp, 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

• 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

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