Head of Finance

About the Role
As Head of Finance, you will own the entire Finance and Legal function at Sky Watch — accounting, FP&A, taxes, compliance, shareholder reporting, and day‑to‑day legal operations. This is a hands‑on leadership role: you will both do the work and build the systems that scale it.

You will be a trusted business partner to the CEO and leadership team — someone with the business acumen, analytical depth, and judgement to translate financial and legal complexity into clear, actionable decisions. Critically, you are not just a finance operator — you are an AI‑forward thinker who sees automation not as a future possibility but as your default approach. You actively experiment with AI tools to eliminate manual work, accelerate reporting, and make Finance a force multiplier for the business.

Forecasted Salary Range :
Base $120,000–$155,000 per annum

What You’ll Do

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, U.S. 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.

Own the financial model in Runway Financial — keep it current, accurate, and ready to answer scenario questions at a moment’s notice.

Translate financial data into clear, concise narratives for the CEO and leadership team.

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.

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.

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 Sky Watch is always ready for due diligence.

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.

What We’re Looking For

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.

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.

Comfort managing legal operations — reviewing contracts, working with external counsel, and keeping legal records organized.

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.

Nice to Haves

Hands‑on experience with Runway Financial.

Familiarity with Stripe revenue reporting and reconciliation in a SaaS or marketplace…