Head of Product & Technology (Questbank)
Top Benefits
About the role
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).
Need more details? Keep reading…
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. Sounds like you? Click below to apply! #LI-LB1 #LI-Hybrid 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.
Not the right fit? Search for Product & Technology jobs in Toronto, Ontario, Canada
About Questrade Financial Group
Questrade is an award-winning low-cost digital alternative to traditional banks that is changing the Canadian financial services industry. We empower Canadians by giving them better, more affordable ways to take control of their financial future by using cutting-edge technology to develop innovative products. Questrade offers Canadians an easy way to invest in securities and foreign currency and provides online wealth management and mortgage through the Questrade Group of Companies, with more financial products in development.
At Questrade, we care deeply about helping Canadians become much more financially successful and secure. We believe in infinite possibilities, not only for our customers but for those who build careers with us. Our exceptional culture and forward-thinking workplace policies make Questrade a great place to work and build a career. We are a collaborative, diverse team that shares the same sense of infinite opportunity. Our beliefs, values, and atmosphere make you feel part of something bigger than yourself.
Throughout our multiple worldwide offices, we are reshaping the way we work, offering flexible options that allow our people to work remotely, from the office, or a hybrid mix of both.
Whether you want to kick-start your career or accelerate it, Questrade is the place for you. We offer rich learning experiences and exciting career path possibilities. Here you will be challenged. You will make your path, constantly moving forward, bringing the future of fintech into existence.
Come shape your future at Questrade.
Similar Jobs
Head of Product & Technology (Questbank)
Top Benefits
About the role
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).
Need more details? Keep reading…
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. Sounds like you? Click below to apply! #LI-LB1 #LI-Hybrid 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.
Not the right fit? Search for Product & Technology jobs in Toronto, Ontario, Canada
About Questrade Financial Group
Questrade is an award-winning low-cost digital alternative to traditional banks that is changing the Canadian financial services industry. We empower Canadians by giving them better, more affordable ways to take control of their financial future by using cutting-edge technology to develop innovative products. Questrade offers Canadians an easy way to invest in securities and foreign currency and provides online wealth management and mortgage through the Questrade Group of Companies, with more financial products in development.
At Questrade, we care deeply about helping Canadians become much more financially successful and secure. We believe in infinite possibilities, not only for our customers but for those who build careers with us. Our exceptional culture and forward-thinking workplace policies make Questrade a great place to work and build a career. We are a collaborative, diverse team that shares the same sense of infinite opportunity. Our beliefs, values, and atmosphere make you feel part of something bigger than yourself.
Throughout our multiple worldwide offices, we are reshaping the way we work, offering flexible options that allow our people to work remotely, from the office, or a hybrid mix of both.
Whether you want to kick-start your career or accelerate it, Questrade is the place for you. We offer rich learning experiences and exciting career path possibilities. Here you will be challenged. You will make your path, constantly moving forward, bringing the future of fintech into existence.
Come shape your future at Questrade.