Financial Controller

We are only reviewing applications submitted through the following link:

https://forms.clickup.com/9017085020/f/8cqbk2w-42777/HQAY19Y2GOAXZ71JUQ

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.

• 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

• 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

• 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

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

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.