Senior Director, Controller

This position is posted by Jobgether on behalf of a partner company. We are currently looking for a Senior Director, Controller in Canada.

This is a high-impact leadership role responsible for shaping and scaling the financial backbone of a fast-growing, technology-driven organization operating at the intersection of fintech, payroll, and production accounting. You will own the integrity of financial systems, ensuring accuracy, transparency, and reliability across all accounting, billing, payroll, and reporting processes. Acting as a key partner to the CFO and cross-functional leadership teams, you will lead the evolution of a modern, AI-enabled accounting function built for scale. This role goes far beyond traditional controllership, combining deep technical accounting expertise with a product-oriented mindset toward financial systems design. You will drive automation, improve financial workflows, and strengthen audit readiness while building a high-performing accounting organization. This is a strategic opportunity for a builder-leader who thrives in complex, fast-moving environments and wants to redefine how modern finance teams operate.

Accountabilities

* Own the accuracy, integrity, and consistency of financial data across all accounting, payroll, billing, procurement, and reporting systems

* Lead the monthly, quarterly, and year-end close processes, ensuring efficiency, reliability, and continuous improvement

* Oversee the design and evolution of financial systems architecture, partnering with Product and Engineering to build scalable solutions

* Drive automation across accounting workflows, leveraging AI and modern tools to reduce manual effort and improve reporting quality

* Ensure audit readiness and maintain a strong internal controls environment across all financial operations

* Lead technical accounting policies and ensure full compliance with GAAP and regulatory requirements in the US and Canada

* Deliver clear, actionable financial reporting and insights to executive leadership to support strategic decision-making

* Build, lead, and scale a high-performing accounting team, including hiring, development, and organizational design

* Oversee tax compliance across multiple jurisdictions, ensuring accuracy and timeliness

* Act as a cross-functional finance leader, promoting financial discipline across Product, Operations, and Go-to-Market teams

Requirements

* 10+ years of progressive experience in accounting and financial operations, with CPA designation required

* Strong background in high-growth SaaS, fintech, or similarly complex, multi-system environments

* Proven experience building and scaling accounting functions with a systems-driven and automation-first mindset

* Deep technical accounting expertise, including revenue recognition and audit readiness leadership

* Experience designing and implementing scalable financial systems in partnership with engineering or product teams

* Hands-on experience leveraging AI tools and automation technologies to optimize accounting workflows

* Strong leadership experience managing and developing high-performing accounting teams

* Excellent communication skills with the ability to translate complex financial concepts into clear business insights

* Strong analytical and problem-solving skills with a builder mentality and comfort in ambiguity

* Experience overseeing multi-jurisdictional tax compliance (US and Canada)

Benefits

* Competitive compensation package aligned with senior finance leadership roles

* Fully remote work across Canada and the United States

* Unlimited paid time off

* Health and dental coverage

* Home office setup allowance for equipment and productivity tools

* Internet and mobile phone reimbursement support

* RRSP/401(k) matching program

* Learning and professional development opportunities

* Opportunity to build and transform a modern, AI-driven finance function at scale

* High-impact leadership role with strong visibility to executive leadership and board-level reporting

How Jobgether Works

We use an AI-powered matching process to ensure your application is reviewed quickly, objectively, and fairly against the role's core requirements. Our system identifies the top-fitting candidates, and this shortlist is then shared directly with the hiring company. The final decision and next steps (interviews, assessments) are managed by their internal team.

We appreciate your interest and wish you the best!

Why Apply Through Jobgether?

Data Privacy Notice: By submitting your application, you acknowledge that Jobgether will process your personal data to evaluate your candidacy and share relevant information with the hiring employer. This processing is based on legitimate interest and pre-contractual measures under applicable data protection laws (including GDPR). You may exercise your rights (access, rectification, erasure, objection) at any time.

We may use artificial intelligence (AI) tools to support parts of the hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our recruitment team but do not replace human judgment. Final hiring decisions are ultimately made by humans. If you would like more information about how your data is processed, please contact us.