skywatch - Head of Finance
Requirements
• 5+ years of progressive Finance experience, with direct ownership of accounting, FP&A, and compliance in a growth-stage technology company. • Strong business acumen and analytical judgement — you think like an operator, not just an accountant. You ask why the numbers look the way they do and what it means for the business. • A CPA designation (or equivalent) is an asset but not a hard requirement — we care far more about what you've built and how you think. • Demonstrated experience with Xero or a comparable cloud accounting platform; fluency across multiple Finance systems. • Hands-on experience with AI and automation tools applied to Finance workflows — you can name specific examples and show your work. • A systems-thinking mindset: you see broken processes and immediately think about how to redesign them, not just work around them. • Comfort managing legal operations — reviewing contracts, working with external counsel, and keeping legal records organized. You don't need to be a lawyer, but you need to know when to call one. • Strong communication skills, with the ability to translate financial and legal complexity into crisp, decision-relevant summaries for a non-technical audience. • Comfort operating in ambiguity at a fast-moving company where priorities shift and the roadmap evolves. • Collaborative, low-ego, and energized by working closely with a leadership team that is deeply engaged in the business. • Hands-on experience with Runway Financial. • Familiarity with Stripe revenue reporting and reconciliation in a SaaS or marketplace context. • Prior experience managing SR&ED claims and the supporting documentation process. • Exposure to US subsidiary operations, multi-currency accounting, or government contract finance. • Experience supporting a fundraise, investor process, or M&A transaction. • Prior experience managing external legal counsel or working alongside a General Counsel at a startup.
Responsibilities
• OWN FINANCE END-TO-END • Manage all accounting operations — AP, AR, payroll, and reconciliations — with clean, audit-ready books at all times. • Close the books by the 15th of each month, every month, without exception. • Own all tax filings and compliance obligations (SR&ED, HST/GST, corporate tax, US sales tax where applicable). • Prepare and deliver shareholder updates, board reporting packages, and investor materials. • Act as the primary relationship owner with external auditors, tax advisors, and banking partners. • DRIVE STRATEGIC FINANCE & FP&A • Own our financial model in Runway Financial — keep it current, accurate, and ready to answer scenario questions at a moment's notice (pricing changes, new products, new investments, headcount shifts, and everything in between). • Translate financial data into clear, concise narratives for the CEO and leadership team — you make the numbers mean something. • Lead annual budgeting and rolling forecasting processes. • Monitor unit economics, cash runway, and key SaaS/marketplace metrics with a forward-looking lens. • Flag risks and opportunities proactively — don't wait to be asked. • AUTOMATE & SYSTEMATIZE EVERYTHING • Identify and eliminate manual, repetitive Finance work through AI tools and system integrations. • Configure and optimize our Finance tech stack (Xero, Runway Financial, Stripe, Plooto, Float, ADP) — you don't need to wait for IT. • Build workflows, automations, and reporting pipelines that allow Finance to scale without proportional headcount growth. • Stay current with new AI applications in Finance and champion experimentation across the function. • MANAGE LEGAL OPERATIONS • Serve as the internal point of contact for all legal matters — contracts, NDAs, commercial agreements, IP, employment, and regulatory compliance. • Manage and coordinate external legal counsel, ensuring work is scoped and executed efficiently. • Maintain organized, up-to-date legal records so that SkyWatch is always ready for due diligence — whether for a fundraise, partnership, or M&A process. • Review and redline routine contracts with support from external counsel on complex matters. • Identify legal risks proactively and flag them to leadership before they become problems.
Benefits
• Competitive compensation including base salary and stock options. • Flexible work environment with the expectation of being in the Kitchener office several days per week. • Generous time-off policy and employee wellness programs. • Transportation stipend. • Employee assistance program. • A front-row seat at a growing company operating in the rapidly expanding Earth observation and geospatial intelligence sector. • Accessibility at SkyWatch
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