Head of Finance

SkyWatch • Kitchener, ON

1d • $120,000 - $155,000 • Hybrid

About The Position

As Head of Finance, you will own the entire Finance and Legal function at SkyWatch — 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.

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.
• 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.

Nice To Haves

• 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.
• 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

• 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.
• 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.
• 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 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.
• Extended health benefits.
• 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.

What This Job Offers

• Job Type: Full-time
• Career Level: Senior
• Education Level: No Education Listed