• We’re seeking a Director of Finance & Operations to join our team. You will serve as the internal owner of finance and operations — driving rigorous reporting, owning compliance, and partnering with senior leadership on the strategic finance work that shapes how we grow
• Financial Reporting: Own the full monthly, quarterly, and annual close cycle — including P&L, balance sheet, and cash flow — producing accurate, timely reporting packages that meet the standards of institutional investors and board stakeholders. Serve as the primary day-to-day relationship owner with our external accounting firm
• AR/AP & Financial Operations: Oversee accounts receivable and accounts payable processes end-to-end with our vendors, ensuring clean execution, timely collections, and accurate records. Identify and implement process improvements to billing, collections, and payment workflows
• Strategic Finance: Partner with the VP of Strategy & Operations on budgeting, forecasting, long-range financial planning, and cash flow management. Build and maintain financial models that translate operational activity into actionable insights, and prepare investor- and board-ready materials as needed
• Compliance & Controls: Manage North American compliance requirements — including federal and state/provincial tax filings, regulatory reporting, and audit readiness. Design and maintain internal controls and finance systems that are accurate, organized, and audit-ready at all times

Benefits

• Dual hubs: experience the best of both worlds with our offices in vibrant Toronto and bustling New York
• Founder access: work shoulder-to-shoulder with our visionary founding team to shape the future of AI
• Growth investment: Accelerate your career with our dedicated professional development budget
• Unlimited time off: recharge and explore with our trust-based, limited paid time off policy
• Comprehensive healthcare: rest easy with our robust health coveage, proioritizing your well-being
• Future-proof savings: Build your financial security through our 401k plan
• Tech enablement: Stay cutting-edge with our technology reimbursement program
• Flexible lifestyle: Achieve work-life harmony with our flexible, trust-based scheduling- Deep familiarity with GAAP financial reporting and the monthly/quarterly close process
• Exceptional attention to detail — you catch errors others miss and hold yourself to an uncompromising standard of accuracy
• 6–10 years of progressive finance experience, ideally within SaaS or technology companies, including ownership of strategic finance
• Exposure to strategic finance functions: budgeting, forecasting, board reporting, and cash flow management
• Advanced Excel or Google Sheets skills; proficiency with accounting platforms such as QuickBooks
• Prior experience working within or reporting to institutional investors, or similarly rigorous reporting structures
• We encourage you to apply if you see a strong (not necessarily perfect) fit
• Demonstrated experience managing external accounting or advisory firm relationships
• Strong command of North American (Canadian and US, cross-border ideal) compliance and tax requirements
• Comfortable operating independently, managing competing deadlines, and knowing when to escalate
• Experience in a lean, high-growth startup where you’ve had to build processes from scratch
• CPA designation
• Familiarity with equity reporting or cap table management in a funded company context- Each journey includes a mix of interviews and a performance challenge. For this role, that might look like:
• 1. Online Application
• 1. Initial Screen with Director of People & Culture
• 1. Interview with Hiring Manager
• 1. Performance Challenge
• 1. Final 1:1 Interviews
• 1. Final Decision
• Generally, this entire process takes around 6 weeks, although the timing can vary due to specific candidate circumstances