Enterprise - Senior Bookkeeper

Segal GCSE LLP•Toronto, ON

9d•$50 - $75•Hybrid

About The Position

We are seeking a highly organized and detail‑oriented Senior Manager / Bookkeeper to support 2 -3 clients, the largest being a private family office, with day‑to‑day financial administration, document management, banking activities, and coordination across multiple entities. This role is ideal for someone who thrives in a confidential, fast‑moving environment and enjoys a wide range of responsibilities—from bookkeeping and cash flow monitoring to dealing with investment reports and philanthropic commitments.

Requirements

Proficiency with QuickBooks and strong Excel/financial literacy skills.
Exceptional attention to detail and ability to manage sensitive information with discretion.
Strong organizational skills and ability to work independently.
Excellent communication and follow‑through.
A Canadian CPA designation or equivalent experience.
Minimum of 5 years of relevant experience in a public accounting firm.
Strong accounting and general ledger, cash receipts, cash disbursements, investment company accounting and Canadian personal and corporate tax.
Proficient in Microsoft Office and QuickBooks Online.
Advanced written and verbal communication skills.
Team player with a positive perspective and approach.
Creative problem solving and experience in delivery of quality client service.

Nice To Haves

Experience in a family office, accounting firm, or financial administration.

Responsibilities

Manage incoming financial documentation, including broker statements, bank statements, CRA correspondence, and accounts payable.
Enter and reconcile monthly bank transactions in QuickBooks.
Reconcile intercompany loan accounts.
Prepare quarterly cash flow reports to monitor the group’s cash position.
Prepare tax estimates for corporate entities.
Assist accounting staff with year‑end entries for each entity.
Prepare cheques and remittance letters for approval/signature, including: Suppliers (business + personal), Personal and corporate tax installments, Shareholder draws, Payroll remittances, RRSP, TFSA, RESP contributions, Insurance premiums (Foundation + shareholders).
Manage bank accounts, including wire transfers, GIC renewals, deposits, and ensuring adequate USD funds.
Monitor Visa account activity and oversee automatic transfers.
Organize and file documents received via mail and portal into the family office’s system.
Handle email follow‑up for the principal, including: Summaries of transactions, Tracking days spent in the U.S., Ordering items online.
Respond to inquiries and requests from family members and their spouses.
Maintain the Foundation’s budget, commitment schedule, and payment tracking.
Coordinate with Bell Kearns on investment reports, tax forms, and ownership documentation.
Provide administrative involvement in real estate entities as required.

Benefits

The hourly rate for this role is $50.00 - $75.00/ hour CAD, based on skills, experience, and education. We benchmark regularly to ensure fair, competitive pay and recognize individual contribution.
Segal supports community involvement through events through our Giving Beyond Today program our annual paid volunteer day.
Firm-wide special events.
Catered lunches.
On-site games (PS5, pool table, foosball).
Team BINGO.
Dedicated mediation room.
Regular event draws.
Free ROM and AGO tickets.
Fun activities through-out the year.
Commitment to creating a workplace where everyone feels valued, respected, and empowered to be their authentic selves.
Fostering an inclusive culture that celebrates diverse backgrounds and perspectives.
Striving to ensure equity and fairness in all aspects of employment— from hiring practices to professional development opportunities.
Accommodation provided as part of the recruitment process.