Director, Product Enablement

Questrade Financial Group (QFG), through its companies - Questrade, Inc., Questrade Wealth Management Inc., Community Trust Company, Zolo, and Flexiti Financial Inc., provides securities and foreign currency investment, professionally managed investment portfolios, mortgages, real estate services, financial services and more. Questrade uses cutting-edge technologies to develop innovative products that give customers better, more affordable ways to take control of their money. 
 
We are everything a traditional financial institution is not. At QFG, you will be constantly moving forward, bringing the future of fintech into existence. You will be a part of a collaborative team that cares deeply about our mission and each other. Your team members will help you conquer challenges, push boundaries and discover what you are truly capable of.
 
At QFG, we have a culture of innovation where technology serves people—both our team and our customers. We see AI as a collaborative and transformative enabler, and we are seeking forward-thinking individuals who can effectively integrate it into their daily work. The ideal candidate will be a catalyst for change, helping us use AI to create a more efficient and rewarding employee experience while also developing cutting-edge solutions that delight and serve our customers. Join us in shaping a future where AI empowers our team to do their best work and helps us deliver unparalleled customer experiences. 

This is a place where you can explore, discover and learn with continuous growth. As a diverse and inclusive place to work, with a hybrid working environment you can unleash your creativity and curiosity with no limits. If you share the same 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

We're looking for a Director of Product Enablement. Could It Be You?

As the Director, Product Enablement, you will be a strategic operational leader responsible for driving product excellence and coordination across our high-priority product lines, including Retail Everyday Banking, Unsecured Lending (Credit Cards, LoC), and Secured Lending (Mortgages). This role reports directly to the Head of Product and is immediately responsible for leading and scaling a dedicated Product Enablement team. You will be the central point of coordination and governance, optimizing the flow of work, data, and communication among Product Management, Engineering, Legal/Compliance, and Operations teams in a high-growth Canadian Fintech environment.

Need more details? Keep reading…

The Director, Product Enablement will be responsible for three core pillars:

1. Strategic Leadership & Team Building

• Lead and grow the Product Enablement team, providing mentorship and structure to foster a culture of operational rigor and continuous improvement.

• Define, implement, and govern the end-to-end Product Development Lifecycle (PDLC), including standardized planning, OKR setting, and roadmap review processes.

• Manage the Product Operations budget, including oversight of vendor relationships and strategic input on spending for the product tech stack.

2. Risk & Regulatory Maturity

• Drive the maturation of the product compliance practice, designing and enforcing governance frameworks that embed complex Canadian regulatory requirements (e.g., OSFI, FINTRAC) directly into the development workflow.

• Establish mandatory risk assessment and audit-readiness protocols, ensuring all new features, especially in Lending, meet regulatory standards prior to launch.

• Own the Launch Readiness (GTM) process, securing cross-functional sign-offs from Legal, Compliance, Marketing, and Operations to ensure successful and compliant product launches.

3. Operational Excellence & Tooling

• Own the Product Technology Stack (e.g., analytics, roadmapping, feedback tools), leading selection, implementation, and driving high user adoption across the organization.

• Establish and maintain a single source of truth for product performance, defining key metrics (KPIs) and building robust dashboards to inform executive and product decision-making.

• Design and manage a rigorous customer feedback loop and intake process, ensuring qualitative and quantitative data is synthesized and prioritized by product teams.

So are YOU our next Director of Product Enablement? You are if you…

• Have 8+ years of experience in Product Enablement, Product Management, or a similar strategic operational leadership role.

• Have 4+ years of experience specifically within the Fintech, Digital Banking, or other highly regulated industry.

• Have demonstrable expertise in digital product lifecycles that require coordination across multiple stakeholders with regulatory accountability.

• Have Proven People Leadership experience, including hiring, managing, and scaling operational or technical teams.

• Have strong regulatory acumen with a track record of implementing compliance and risk controls into a product development environment, ideally within Canada.

• Have expertise in strategic product tooling selection and governance, with proven ability to leverage data to drive execution.

• Have deep experience developing and launching products in an Agile, Scrum, or Lean environment.

Additional kudos if you have…

• Experience at a high velocity venture backed startup.

• MBA or advanced degree in a related field.

• Experience launching products across multiple Canadian provinces or with inter-provincial regulatory requirements

Sounds like you? Click below to apply

#LI-KS2 | #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.