AI-forward finance leadership at SkyWatch centers on accounting, FP&A;, taxes, compliance, and legal operations. Build scalable systems while advising business leaders.
As Head of Finance, you own SkyWatch’s entire Finance and Legal function. You manage accounting, reporting, forecasting, tax obligations, compliance, and day-to-day legal operations. The role partners with the CEO and leadership team, translating complex financial and legal matters into actionable decisions. You will also use AI tools to reduce manual work and accelerate reporting.
Key Responsibilities: Manage AP, AR, payroll, reconciliations, and audit-ready books
Close monthly books by the 15th
Own tax filings and compliance obligations
Prepare shareholder, board,



and investor reporting materials
Lead external auditor, tax advisor, and banking relationships
Requirements: Business acumen and analytical depth
Judgement translating complexity into transparent decisions
Experience owning finance and legal functions
AI-forward approach to automation and reporting
Ability to manage hands-on operational work
Lead SkyWatch finance and legal operations through accounting, FP&A;, compliance, reporting, and AI-enabled automation.

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📌 Head of Finance and Legal (Ontario)
🏢 SkyWatch
📍 Ontario