Short Term Rental Property Manager Jobs in Toronto, ON

TBROS Group is a founder-led holding company operating three growing businesses with distinct focuses:

• Kasu Capital – a U.S. real estate investment fund

• Sozul – a luxury short-term rental property portfolio

• RevWhisper – an AI-powered revenue optimization platform for short-term rental operators

While each business operates independently, they share one thing in common: a commitment to building scalable businesses through smart systems, thoughtful decision-making, and a hands-on approach.

We operate with a lean team where every person has meaningful ownership and the opportunity to make a measurable impact. If you enjoy solving problems, improving processes, and working closely with leadership in a collaborative environment, you'll find plenty of opportunities to grow here.

TBROS Group is looking for an experienced Senior Accountant to oversee accounting operations across Kasu Capital, Sozul, and RevWhisper. This is a hands-on role responsible for owning the full accounting cycle across multiple entities, from month-end close and financial reporting to treasury, banking, reconciliations, and accounts payable.

Reporting directly to the Co-Founders, you'll also provide guidance to administrative team members who support finance and operations while helping establish scalable financial processes as the businesses continue to grow.

Success in this role means delivering timely, accurate financial reporting, improving month-end close efficiency, maintaining strong financial controls, and creating repeatable processes that support better business decisions.

• Own the full month-end close across multiple entities and deliver accurate, timely financial statements

• Prepare management reporting packages including profit and loss statements, balance sheets, cash flow reporting, budget-to-actual analysis, and financial insights

• Maintain charts of accounts, intercompany transactions, eliminations, and consistent accounting policies across the organization

• Perform monthly balance sheet reconciliations and maintain organized supporting documentation

• Manage banking activities across multiple entities, including CAD and USD accounts, cash positioning, and intercompany transfers

• Reconcile bank accounts, credit cards, merchant accounts, Stripe transactions, and property management revenue

• Monitor cash flow and identify upcoming funding needs

• Oversee the complete accounts payable process, including vendor onboarding, invoice management, approvals, and payment processing

• Administer Ramp expense management, company card programs, and expense coding

• Maintain organized vendor records, contracts, and financial documentation

• Manage and mentor administrative staff supporting finance and operations

• Build and improve accounting processes, internal controls, and documentation that scale with company growth

• Support fund accounting and investor reporting for Kasu Capital

• Maintain property-level financial reporting for Sozul

• Manage service revenue reporting and Stripe reconciliations for RevWhisper

• Coordinate with external accountants, tax advisors, auditors, fund administrators, and cross-border finance partners in Canada and the U.S.

• 5+ years of progressive accounting experience with hands-on ownership of the full month-end close process

• Experience managing accounting across multiple legal entities

• Strong background in banking, treasury, reconciliations, and accounts payable

• Hands-on experience using QuickBooks Online

• Experience managing financial operations involving both Canadian and U.S. currencies

• Previous experience supervising or mentoring finance or administrative staff

• Comfortable using AI tools to improve reporting, automate repetitive tasks, and increase efficiency

• Exceptional attention to detail with strong organizational skills and the ability to manage confidential financial information

• CPA designation or active CPA candidate

• Experience with Ramp, Stripe, Airtable, U.S. GAAP, GST/HST, sales tax, 1099 reporting, or cross-border tax coordination

• Fund accounting or real estate investment accounting experience

• Experience with investor reporting, capital accounts, distributions, or waterfalls

• Short-term rental, hospitality, or property management accounting experience

• Experience with service revenue recognition, client billing, and revenue reporting

• Experience building accounting systems and processes within a growing entrepreneurial company

Compensation: $100,000-130,000$ CAD annually, based on experience

Benefits:

• Comprehensive benefits package

• Healthcare spending or reimbursement accounts

• Hybrid work environment

• Opportunity to work directly with company founders

• Exposure to multiple growing businesses across real estate, hospitality, and technology

Schedule: Full-time

Location: Hamilton, Ontario, Canada