Company Description:

SkyWatch is at the forefront of revolutionizing how earth observation data is accessed and utilized globally. Our innovative platform empowers businesses, researchers, and governments to easily integrate satellite data into their operations, driving informed decision-making and unlocking new opportunities for growth and efficiency. Founded on the principle of democratizing access to space-based technology, SkyWatch provides a seamless interface that aggregates data from numerous satellite sources, offering unparalleled access and insights. Whether monitoring agriculture, managing infrastructure, or advancing scientific research, our scalable solutions cater to diverse industries with a commitment to reliability, security, and sustainability.

Our Products:

Our suite of applications is tailored to meet the diverse needs of users on the SkyWatch platform. Whether you are an individual purchasing data for a project, a business seeking to store and share geospatial data, a GIS specialist in need of imagery for maps or workflows, a developer looking to build innovative solutions with our API, or a data provider seeking to sell to our user network, you can do it with SkyWatch.

Our Culture:

Culture is the personality of a company. It is our company's shared beliefs, values, and practices. At SkyWatch, our culture is incredibly important to us, and we practice it every day. Both as a company and in our products, we value simplicity, dependability, and empathy. Let’s face it — the best jobs boil down to a handful of things: getting the chance to work with amazing people in a great culture with leaders who have your back while pursuing a vision that you can get passionate about.

Please note that SkyWatch may use AI throughout various portions of the talent process.

About the Role

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.

Forecasted Salary Range: Base - $160,000-$190,000/annum

What You'll Do

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.

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. 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.

Nice to Haves

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.

What We Offer

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.
A front-row seat at a growing company operating in the rapidly expanding Earth observation and geospatial intelligence sector.

Accessibility at SkyWatch

At SkyWatch, we believe every candidate deserves a fair and inclusive experience. If you require an accommodation at any stage of the recruitment process, please let us know — we're happy to work with you to ensure your needs are met.

To request an accommodation, please advise any member of the talent team or contact us at accommodation@skywatch.com.

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