Head of Product & Technology (Questbank)

Questrade Financial Group•Toronto, ON

4d•Hybrid

About The Position

Questrade Financial Group (QFG) is seeking a Head of Product & Technology for Questbank. This role bridges product strategy and technical infrastructure, leading a team of product directors, managers, engineers, designers, and data scientists to build secure, scalable, and customer-centric financial solutions. The ideal candidate will be a catalyst for change, using AI to transform financial services and deliver unparalleled customer experiences. This executive role involves transforming legacy systems into modern, cloud-native architectures while adhering to strict Canadian banking sector compliance, security, and stability standards (OSFI). QFG offers a diverse, inclusive, and hybrid workplace that encourages creativity and curiosity.

Requirements

10+ years of progressive leadership experience in product management and/or software engineering.
At least 5 years in an executive or director-level capacity.
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.

Responsibilities

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.