Job description

Position Overview

We are seeking a meticulous and highly skilled Financial Controller to manage complex multi-entity financial operations remotely. This role requires impeccable attention to detail, organizational strength, and the capability to ensure financial accuracy and compliance across various entities.

Key Responsibilities

Lead the weekly and monthly close procedures for multiple entities with full financial reconciliation.
Ensure all financial records are balanced with no uncategorized amounts.
Oversee accounts payable processes, vendor payments, and manage W-9/1099 documentation and approval workflows.
Actively monitor cash flow, account balances, and maintain tax reserve schedules.
Administer payroll processing and reconciliation through Deel platform.
Maintain well-organized, audit-ready financial documentation and data rooms.
Collaborate with CPAs, legal counsel, FP&A teams, and company leadership to manage compliance and reporting tasks.
Drive automation initiatives for reconciliation and reporting through integration of available tools.
Track budgets versus actual expenses and alert on any irregularities or financial risks.
Ensure compliance with filing deadlines and uphold strong internal financial control systems.

Collaboration and Communication

Work in close partnership with the CEO, FP&A, Senior Bookkeeper, CPAs, and legal partners.
Use ClickUp to maintain visibility on finance workflows and track progress systematically.
Provide structured and proactive financial updates without the need for follow-ups.
Escalate financial risks, missing approvals, and operational bottlenecks promptly.
Engage in strategic and operational financial discussions to support cross-functional initiatives.

Qualifications and Skills

Proven experience managing financial operations, reconciliations, and closing activities across multiple entities.
In-depth knowledge of U.S. GAAP principles, accounts payable and receivable processes, audit preparedness, and regulatory compliance.
Hands-on experience with finance tools such as QuickBooks Online, Deel, ClickUp, and other modern operational software.
Exceptional operational discipline, organizational ability, and documentation skills.
Excellent discretion and accuracy handling sensitive financial workflows.
Proactive communicator with a strong sense of ownership and accountability.
Comfortable working independently in dynamic, fast-paced environments.
Prior experience supporting founders, startups, or fast-growing companies is highly advantageous.

Ideal Candidate Profile

Highly attentive to discrepancies and acts swiftly to resolve them.
Operates with great precision and responsibility.
Approaches finance functions with a systems-thinking and control-oriented mindset.
Identifies and resolves issues preemptively.
Maintains composure under pressure and adapts to changing priorities.
Takes initiative without awaiting supervision or instructions.

About the Company

Trolley AI is a rapidly expanding creative operations firm delivering impactful digital and marketing solutions to leading clients. The company embraces an AI-driven, founder-minded approach emphasizing ownership, execution excellence, and continuous operational improvement.

Benefits

Work fully remotely with flexible scheduling and time off.
Access to cutting-edge AI tools to enhance productivity.
Opportunity to work directly alongside company leadership.
Clear pathways for long-term career advancement.
Join a high-trust, fast-paced, and collaborative team culture.