About Us

We are a dynamic and growing family office with a diverse portfolio that includes real estate investments, hospitality franchises (Second Cup, Freshii, Noodle Box), and private equity holdings. Our operations span multiple active corporations, each with distinct reporting needs and financial workflows. We are seeking a detail-oriented, proactive Bookkeeper who thrives in a multi-entity environment and can help us stay sharp and scalable.

• Note: This position is currently 100% remote. However, we are seeking candidates based in the Toronto, Ontario, GTA as we plan to transition into an office setting in the near future.

Key Responsibilities

• Accounting & QuickBooks Management
• Maintain full-cycle bookkeeping across multiple active QuickBooks entities
• Post journal entries, reconcile accounts, manage intercompany loans
• Ensure accurate recording of property mortgages (principal & interest)
• Handle daily, weekly, and monthly bank reconciliations
• Ensure compliance with HST filings for each entity
• Process and manage payroll across all active entities, ensuring compliance with federal and provincial regulations
• Identify opportunities to streamline workflows and improve automation across entities
• Coordinate with external accountants for year-end reviews and tax filings
• Property & Investment Tracking
• Manage and review quarterly cash calls across investment properties
• Track investor contributions, ownership interest and returns
• Record capital contributions and partnership transactions accurately in the books
• Support property management invoicing and reconciliation
• Assist in cash flow forecasting and variance analysis for investment properties
• Franchise Operations Oversight
• Enter high-level sales data from POS systems (detail stays in POS)
• Track Cost of Goods Sold (COGS) and employment costs
• Work closely with operations to ensure alignment of financial reports with reality
• Prepare franchise-level financial summaries and liaise with store managers to ensure accuracy of COGS and payroll allocations
• Collaboration & Reporting
• Work directly with our Controller and outsourced bookkeeper
• Assist in preparing financial reports, summaries, and dashboards for leadership
• Support VC and PE investment tracking across startups and portfolio companies
• Prepare ad hoc reports and provide financial insights to support strategic decision-making
• Qualifications
• 5+ years of full-cycle bookkeeping experience
• Strong proficiency in QuickBooks Desktop/Online (QBO)
• Direct experience with multi-entity bookkeeping and intercompany transactions is a must
• Knowledge of property and investment accounting, including cash calls, capital contributions and distributions
• Experience with hospitality/franchise operations preferred
• Understanding of HST filings, and intercompany loan tracking
• Experience managing payroll, including compliance with federal and provincial regulations
• Comfortable working with high-level summaries and also diving into granular transaction reviews when needed
• Strong Excel or Google Sheets skills
• Strong organizational and time-management skills; able to prioritize across multiple entities

High attention to detail and accountability mindset…

• Experience with POS systems or franchise management tools
• Familiarity with VC/PE tracking tools
• Prior work with family offices or high-net-worth individuals

Why Join Us?

• Fast-paced, entrepreneurial environment
• Exposure to real estate, hospitality, private equity, and franchising
• Room for growth and learning from strategic-level operations
• Be part of a values-driven team with an eye on both detail and the big picture
• Opportunity to work closely with senior leadership and gain exposure to strategic-level finance operations
• Collaborative, values-driven culture with opportunities for professional growth
• Opportunity to help shape processes and systems in a growing family office

To Apply
Please send your resume and a short note explaining why you’re the perfect fit
Job Type: Full-time
Pay: $26.88-$32.37 per hour

Benefits:

• Work from home

Education:

• Bachelor’s Degree (preferred)

Experience:

• Accounting: 5 years (required)

Language:

• English (required)

Work Location: Remot

Key Responsibilities

• Accounting & QuickBooks Management
• Maintain full-cycle bookkeeping across multiple active QuickBooks entities
• Post journal entries, reconcile accounts, manage intercompany loans
• Ensure accurate recording of property mortgages (principal & interest)
• Handle daily, weekly, and monthly bank reconciliations
• Ensure compliance with HST filings for each entity
• Process and manage payroll across all active entities, ensuring compliance with federal and provincial regulations
• Identify opportunities to streamline workflows and improve automation across entities
• Coordinate with external accountants for year-end reviews and tax filings
• Property & Investment Tracking
• Manage and review quarterly cash calls across investment properties
• Track investor contributions, ownership interest and returns
• Record capital contributions and partnership transactions accurately in the books
• Support property management invoicing and reconciliation
• Assist in cash flow forecasting and variance analysis for investment properties
• Franchise Operations Oversight
• Enter high-level sales data from POS systems (detail stays in POS)
• Track Cost of Goods Sold (COGS) and employment costs
• Work closely with operations to ensure alignment of financial reports with reality
• Prepare franchise-level financial summaries and liaise with store managers to ensure accuracy of COGS and payroll allocations
• Collaboration & Reporting
• Work directly with our Controller and outsourced bookkeeper
• Assist in preparing financial reports, summaries, and dashboards for leadership
• Support VC and PE investment tracking across startups and portfolio companies
• Prepare ad hoc reports and provide financial insights to support strategic decision-making
• Qualifications
• 5+ years of full-cycle bookkeeping experience
• Strong proficiency in QuickBooks Desktop/Online (QBO)
• Direct experience with multi-entity bookkeeping and intercompany transactions is a must
• Knowledge of property and investment accounting, including cash calls, capital contributions and distributions
• Experience with hospitality/franchise operations preferred
• Understanding of HST filings, and intercompany loan tracking
• Experience managing payroll, including compliance with federal and provincial regulations
• Comfortable working with high-level summaries and also diving into granular transaction reviews when needed
• Strong Excel or Google Sheets skills
• Strong organizational and time-management skills; able to prioritize across multiple entitie

High attention to detail and accountability mindset…

• Experience with POS systems or franchise management tools
• Familiarity with VC/PE tracking tools
• Prior work with family offices or high-net-worth individual