Vice President, Finance & Operations

Drive Capital; Kitchener; On-site; CAD 150,000 - 210,000; Full time

Benefits offered by this job

Stock options

Extended health benefits

Flexible work environment in Kitchener

Generous time-off policy

Transportation stipend

Employee assistance program

Front-row seat at growth

Job summary

SkyWatch is seeking a senior finance and operations leader to partner with the CEO and board, owning planning, reporting, and compliance for a growth-stage tech company. You will build a scalable, AI-first finance function, manage end-to-end processes from accounting to contracts, and drive corporate performance across data, software, and services.

You will work closely with executive leadership in a fast-paced, collaborative environment, balancing strategic oversight with hands-on execution in

Qualifications

• 8+ years of progressive finance experience in growth-stage technology companies.
• Leadership of a finance function and collaboration with operations or legal.
• Fluency across cloud accounting, planning, billing, payments and payroll platforms.
• Hands-on experience applying AI and automation to finance workflows.
• Experience with contract management and tracking financial obligations.
• CPA or equivalent; government contracts or grants experience preferred.
• Experience with multi-currency accounting and US subsidiary operations preferred.

Responsibilities

• Build financial planning and FP&A: annual budget, rolling forecasts, revenue by data/software/services.
• Own finance end to end: accounting operations, month-end close, tax & compliance filings.
• Run government funding and contract compliance: grants, tax credits, reporting.
• Run operations: vendor management, workplace, and company cadence.
• Run contract management and compliance: manage agreements, renewals, and payments.
• Build it, then automate it: implement AI-first finance/ops systems and pipelines.

Skills

Finance leadership

AI automation

FP&A ownership

Contract compliance

Education

CPA or equivalent

Tools

Cloud accounting platforms

Billing and payroll systems

AI tools for finance

Job description

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.

The mission

Turn SkyWatch into a high-performing, revenue-generating machine.

You will build the financial and operating backbone that lets a small team run like a much larger one: every dollar, contract and process tied to growth, and every number in front of the people who can act on it. The role brings Finance, Operations and contract management together under one leader.
The role

You are the CEO's business partner on how the company runs: the plan, the numbers and the operating rhythm. Our revenue is a mix of data, software and professional services, and it is transacted three ways: prepaid commitments, credit card and monthly billing. Turning that mix into a plan the company can run on, and a forecast it can trust, is the core of this job. You make sure the company is always audit-ready and diligence-ready.

This is a role for a builder. There is no finance team waiting for instructions and no playbook to inherit. In the early days you will roll up your sleeves and build the financial plan, the monthly close and the operating cadence yourself, then automate them so they run without you.

Key responsibilities

• Build financial planning and FP&A. Maintain our existing financial model and turn it into the operating plan: annual budget, rolling forecasts, and a clear view of revenue across data, software and services and across prepaid, card and monthly-billed customers. Monitor unit economics, cash runway, prepaid balances and subscription metrics, and deliver the board package, shareholder updates and investor materials.

• Own finance end to end. Accounting operations (AP, AR, payroll, reconciliations) with clean, audit-ready books; close by the 15th of every month; tax and compliance filings, including SR&ED, HST/GST, corporate tax and US sales tax where applicable; relationships with auditors, tax advisors and banking partners.

• Run government funding and contract compliance. Own the finance side of government contribution agreements, grants and tax-credit programmes: eligible-cost tracking, claims and evidence, reporting schedules and covenant compliance, alongside the programme owners.

• Run operations. Own the company operating cadence, annual planning and company-wide targets; the vendor and contract base; the workplace; and the processes that let a small team operate like a much larger one.

• Run contract management and compliance. Stand up the system where every agreement lives, then track and operate to what we have signed: when the next supplier payment is due and how much, when an agreement expires or renews, how many credits a customer bought against how many rolled over. Weigh in on risk and on whether we can meet the reporting, AP and AR obligations in a deal before it is signed. Contract structure, drafting and negotiation stay with the executive team, with outside counsel as an advisory layer.

• Build it, then automate it. Stand up the finance and operations systems yourself, replace manual work with AI tools and integrations, and build reporting pipelines that let the function scale without proportional headcount.

Who you are

• An operator with a finance core. You have owned accounting, FP&A and compliance, and you care more about the decision a number drives than the number itself.

• A builder. You have built a finance or operations function from a blank page, not just run one. You are happy doing the work yourself before there is anyone to delegate it to.

• AI-first by habit. You can name the specific workflows you have automated and show the work.

• A systems thinker. When a process is broken you redesign it rather than work around it.

• A clear communicator. You turn financial and operational complexity into crisp, decision-ready summaries for a non-technical audience.

Qualifications

• 8+ years of progressive finance experience in growth-stage technology companies, including direct ownership of accounting, FP&A and compliance.

• Prior leadership of a finance function and at least one adjacent function, such as operations or legal, including building one from an early stage.

• Fluency across cloud accounting, planning, billing, payments and payroll platforms.

• Hands-on experience applying AI and automation to finance or operations workflows.

• Experience standing up contract management and tracking financial obligations across supplier and customer agreements.

• CPA or equivalent. Asset

• Experience with government contribution agreements, grants, SR&ED or government contract finance. Strongly preferred

• Experience with a fundraise, investor process or M&A transaction, US subsidiary operations or multi-currency accounting. Preferred

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.

  Why SkyWatch

• Scope. Finance and Operations, with a direct line to the CEO and board, at a company small enough that every system you build is used by everyone.

• Leverage. A blank page and a mandate to build an automated, AI-first function from day one, aimed squarely at growth.

• The frontier. A front-row seat in the fast-growing 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 [e-mail].