Head of Product & Technology

Questrade is on a mission to help Canadians to become much more financially successful and secure.

For nearly 30 years, Questrade Financial Group has been delivering on that mission through investing, banking, mortgages, and real estate. Together, we tilt finance in favour of ambitious Canadians, creating new ways for them to seize the financial future they deserve.

We're looking for people who are ready to enter their career inflection point. Mission-driven, exceptional folks that never settle. The work here is hard because the responsibility is real. If that's the standard you've been looking for, keep reading.

Req #4190

The return on your career investment

• Compensation and incentives built to reward the value you bring.
• RRSP matching of up to 6%.
• Health and wellness resources and programs, including $5,000 in mental health practitioner coverage.
• $5,000 in tuition subsidies for job-related courses, every year.
• 100% parental top-up, up to 26 weeks for birthing parents and 18 weeks for non-birthing parents.
• A hybrid environment, with at least three days in the office built for working together.
• Paid vacation, personal, and sick days.
• A community care day to give back to the causes you care about.

This job posting is for an existing vacancy.

We’re looking for our next Head of Product & Technology

The Head of Product & Technology will bridge the gap between product strategy and technical infrastructure. You will lead a high-performing, co-located team of product directors and managers, engineers, designers, and data scientists to build secure, scalable, and customer-centric financial solutions.

This is a critical executive role for a leader who thrives on transforming legacy paradigms into modern, cloud-native architectures while maintaining the rigorous compliance, security, and stability standards required by the Canadian banking sector (OSFI).

The mandate

In this role, you will:

• Own and execute the end-to-end product and technology roadmap, aligning it with Questbank’s overarching business goals.
• Drive a product-led culture that leverages data analytics, user research, and continuous feedback loops to deliver exceptional digital banking experiences.
• Partner with business unit leaders to ensure the product stack directly enables revenue growth, customer acquisition, and retention.
• Oversee the evolution of Questbank’s architecture toward modern, API-first, and cloud-native solutions that support the product vision.
• Foster a robust engineering culture rooted in DevOps, CI/CD automation, clean code practices, and technical debt management.
• Evaluate, negotiate with, and manage critical third-party tech vendors, core banking providers, and FinTech partners.
• Ensure all product features and technology deployments comply with OSFI guidelines (specifically B-10, B-13), FCAC, and privacy regulations (PIPEDA).
• Mentor and scale a diverse team of product managers, engineers, and agile practitioners, promoting a culture of psychological safety, accountability, and continuous learning.
• Optimize the cross-functional squad model to eliminate silos between product discovery and technical delivery.
• Primary P&L leader for the bank

You’re ready for this mandate if you have the following qualifications

• 10+ years of progressive leadership experience in product management and/or software engineering, with at least 5 years in an executive or director-level capacity.
• A deep understanding of the Canadian financial services landscape, including retail/commercial banking, payment networks (Interac, Payments Canada modernisation), and core banking systems.
• Bachelor’s or Master’s degree in Business, Computer Science, Engineering, or a related discipline.
• Expertise in modern product discovery frameworks and Agile/Scrum/SAFe methodologies.
• Strong literacy in cloud computing (AWS, Azure, or GCP), microservices architecture, and modern data platforms.
• Exceptional communication and stakeholder management skills; ability to translate complex product and technical concepts into business outcomes for the C-suite and Board of Directors.

Enter your career inflection point. Apply now.

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Technology and AI

We mix human ingenuity with advanced technology. For ambitious builders like you, we provide the latest technology to enable your creativity. You'll have everything you need to build the best outcomes and products for our clients.

Diversity and Inclusion

At Questrade Financial Group of Companies, we’re committed to fostering a diverse, inclusive, and accessible work environment where individuals are treated with dignity and respect. Our global team reflects the diversity of the communities we serve and operate in.

Accessibility statement

Candidates selected for an interview are contacted directly. If you require accommodation during the recruitment or selection process, please let us know. We will work with you to meet your needs.

AI in hiring

Questrade Financial Group of companies Applicant Tracking System uses artificial intelligence (AI) for application screening. The AI system operates on predetermined criteria, with final decisions subject to human review.