Head of Finance

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 companys 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. Lets 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 - $160000-$190000/annum

What Youll 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 moments 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 dont 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 dont 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 Were 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 youve 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 dont 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 were 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

Required Experience:

Director

Employment Type : Full-Time
Department / Functional Area: Finance
Experience: years
Vacancy: 1