Description:

Bookkeeper

Greybox Legal  ·  Mid-level  ·  Full-time

About Greybox Legal

Greybox Legal is a boutique law firm built for clients who move capital, close deals, and plan legacies. We operate at the intersection of business, tax, and private capital — advising founders, owner-operators, family enterprises, and high-net-worth individuals who demand precision, discretion, and clarity when it matters most.

Our work spans corporate structuring, tax planning, mergers and acquisitions, and private client matters — including estate planning and intergenerational wealth. We think strategically, act confidentially, and measure our success by the value we create for our clients. Law is our tool. Value is our outcome.

About the Role

We are seeking a detail-oriented and experienced Bookkeeper to join the Greybox Legal team. This is a critical role in our operations — you will own the firm’s day-to-day financial functions, from trust accounting and payables to filings, cash flow, and reporting. You take pride in clean books, stay ahead of deadlines without being reminded, and have the confidence to ask the right questions when something is unclear. You understand that in a legal environment, precision and compliance are non-negotiable — and you bring both naturally.

Key Responsibilities

• Maintain accurate general ledger, accounts payable, accounts receivable, and bank reconciliations in QBO, with matters tracked through Clio.
• Manage and reconcile trust accounts in strict compliance with Law Society rules, with zero tolerance for error.
• Own the accounts payable cycle end-to-end — processing, approvals, and payment execution through Plooto — ensuring all vendor and supplier obligations are met on time.
• Maintain a clear view of upcoming payable deadlines and proactively flag any cash flow pressures to the managing partner before they become issues.
• Process client invoices, monitor outstanding balances, and follow up on overdue accounts in a professional and timely manner.
• Process payroll and expense claims accurately and on time.
• Manage all required filings — GST/HST, payroll remittances, and other statutory obligations — meeting every deadline without exception.
• Prepare and maintain regular cash flow forecasts, keeping the partners informed of the firm’s financial position and any forward-looking concerns.
• Prepare monthly, quarterly, and year-end financial reports and liaise with external accountants for year-end close.
• Ask questions when something is unclear — and do so early. We value good judgement over assumptions, and expect this role to seek clarity proactively rather than proceed on guesswork.

What Success Looks Like

The books are always current and reconciled. Trust accounts are airtight. No filing deadline is ever missed. Payables are processed through Plooto on time, every time. The partners have a clear picture of cash flow without having to ask for it. When something unusual comes up, you flag it early and ask the right question rather than guessing. You’re a trusted and steady presence in the firm — someone who takes full ownership of the financial function and keeps everything running with quiet confidence.

Why You’ll Love Working Here

• Competitive compensation.
• Comprehensive health and dental coverage.
• Generous vacation and paid time off.
• Convenient on-site parking.
• Support for professional growth and development.
• A collegial, collaborative team environment.