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Controller

About us

Upstay offers short-term rentals across the United States, Eastern Canada, and South America. Our team of 160+ employees manages 400+ properties on behalf of owners. We treat every property in our portfolio as an investment with a focus on maximizing profit without sacrificing best-in-class hospitality for our guests.

Our mission is to empower homeowners by unlocking high ROI opportunities usually reserved for institutional investors.

The following opportunity is available: Controller

The ideal candidates will have years of experience in a senior financial leadership role with excellent understanding of finance, strategy, and corporate development.

• Plan, organize, and direct the financial operations of the company to ensure fiscal health and regulatory compliance;
• Establish and implement internal controls, accounting policies, and procedures to safeguard assets and support organizational growth;
• Evaluate financial reporting systems, accounting procedures, and investment activities to recommend improvements and reduce financial risk;
• Coordinate the preparation of operating and capital budgets, financial statements, forecasts, and variance analysis for executive review;
• Authorize expenditures, monitor financial performance, and ensure adherence to approved budgets;
• Provide senior leadership with financial insights and recommendations to support strategic decision-making and long-term business planning;
• Lead external audit processes and liaise with auditors, banks, and tax authorities as needed;
• Oversee payroll, accounts receivable/payable, tax filings, and all general accounting functions;
• Recruit, manage, and mentor finance team members, ensuring performance, compliance, and continuous improvement across the department.

Requirements:

• College or university diploma in Business Administration, Commerce Finance, or Project Management, or related field;
• Minimum of five (5) years of progressively responsible experience in financial management, accounting, or controllership functions, preferably in a senior leadership capacity.
• Strong strategic planning and organizational development skills;
• Exceptional financial acumen and proficiency in budgeting, forecasting, and financial analysis;
• Superior English language skills;

Additional Skills and Competencies:

• Skilled in analyzing complex financial data and identifying actionable trends
• Strong financial judgment and decision-making under pressure
• Proven leadership in managing accounting and finance teams
• Effective communicator with senior management and external partners
• High accuracy in financial reporting and regulatory compliance

Compensation:

• This is a full-time, permanent position with at least 30 hours of work per week;
• The remuneration will be set at CAD $100,000.00 per annum; overtime rate applies after 44 hours of work per week;
• Comprehensive benefits package!
• Location of Work: 727 Somerset St W., Ottawa, ON K1R 7G2

Why Upstay?

At Upstay, we’re passionate about revolutionizing the hospitality industry through innovation and excellence.

Joining our team means being part of a dynamic, collaborative environment where your ideas are valued, and your contributions make a real difference.