Head of Product & Technology (Questbank)

Community Trust Company; Canada; On-site; CAD 180,000 - 270,000; Full time

Benefits offered by this job

Health & wellbeing resources

Paid vacation & sick days

Hybrid work environment

Competitive compensation

Career growth opportunities

Community involvement

Job summary

Questrade Financial Group, via Questbank, seeks a Head of Product & Technology to bridge product strategy and technical infrastructure. Lead a cross-functional team to build secure, scalable financial solutions in a hybrid workplace.

The role demands 10+ years in leadership with a track record of delivering modern, cloud-native systems while maintaining rigorous compliance and security standards for banking.

Qualifications

• 10+ years of progressive leadership in product management or software engineering.
• At least 5 years in an executive or director-level capacity.
• Bachelor's or Master's degree in Business, CS, Engineering, or related discipline.

Responsibilities

• Own and execute the end-to-end product and technology roadmap, aligning with Questbank goals.
• Drive a product-led culture using data analytics and user research.
• Partner with business units to enable revenue growth and customer acquisition.
• Oversee evolution to API-first, cloud-native solutions supporting the vision.
• Foster a DevOps culture with CI/CD, clean code, and debt management.
• Evaluate and manage critical third-party vendors and FinTech partners.
• Ensure OSFI (B-10, B-13) and privacy (PIPEDA) compliance.
• Mentor a diverse team of product managers, engineers, and agile practitioners.
• Optimize cross-functional squads to reduce silos between discovery and delivery.
• Primary P&L leader for the bank.

Skills

Leadership

Product management

Software engineering

Cloud computing

Microservices

Agile / SAFe

Stakeholder management

Communication

Education

Bachelor's or Master's in Business, CS, Engineering, or related

Tools

AWS

Azure

GCP

Job description

Head of Product & Technology (Questbank)

5700 Yonge St, North York, ON M2M 4K2, Canada

Job Description

Posted Tuesday, July 28, 2026 at 4:00 AM

Questrade Financial Group (QFG), through its companies - Questrade, Questbank, Questrade Wealth Management, Community Trust Company, Zolo, and Flexiti, provides securities and foreign currency investment, professionally managed investment portfolios, mortgages, real estate services, financial services and more. We use cutting-edge technology to help Canadians become much more financially successful and secure.

At QFG, we combine human-centric collaboration with AI-driven innovation to redefine financial services. The ideal candidate will be a catalyst for change, using AI to transform and deliver unparalleled customer experiences and shaping a future where AI empowers our teams to do their best work.

Join our diverse, inclusive, and hybrid workplace to unleash your creativity and nurture your curiosity without limits. If you share this sense of infinite possibility, come shape your future at QFG.

What's in it for you as an employee of QFG?

• Health & wellbeing resources and programs
• Paid vacation, personal, and sick days for work-life balance
• Competitive compensation and benefits packages
• Work-life balance in a hybrid environment with at least 3 days in office
• Career growth and development opportunities
• Opportunities to contribute to community causes
• Work with diverse team members in an inclusive and collaborative environment

This job posting is for an existing vacancy.

We're looking for our next Head of Product & Technology. Could It Be You?

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).

In this role, responsibilities include but are not limited to:

• 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

So are YOU our next Head of Product & Technology? You are if you…

• Have 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.
• Have a deep understanding of the Canadian financial services landscape, including retail/commercial banking, payment networks (Interac, Payments Canada modernisation), and core banking systems.
• Have a Bachelor's or Master's degree in Business, Computer Science, Engineering, or a related discipline.
• Have expertise in modern product discovery frameworks and Agile/Scrum/SAFe methodologies.
• Have strong literacy in cloud computing (AWS, Azure, or GCP), microservices architecture, and modern data platforms.
• Have 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.

At Questrade Financial Group of Companies, with multiple office locations around the world, we are committed to fostering a diverse, inclusive and accessible work environment. This is an environment where individuals are treated with dignity and respect. Here, the unique skills and experience you bring will be valued. You will be supported and motivated, so that you can harness your unlimited potential. Our team reflects the diversity of the communities we serve and operate in. Having a collaborative and diverse team helps us push boundaries to bring the future of fintech into existence- not only for the benefit of our customers, but for those who build their career with us.

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

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