Director, Strategy

Get AI-powered advice on this job and more exclusive features. 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. At QFG, we are everything a traditional financial institution is not. You will be constantly moving forward, bringing the future of fintech into existence. You will be part of a collaborative team that cares deeply about our mission and each other. 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. We’re looking for our next Director, Strategy. The Director, Strategy will act as a lead architect of Questrade Financial Group’s future growth. In this high‑visibility role, you will be responsible for defining where we play and how we win. You will lead the evaluation of organic and inorganic growth opportunities, while simultaneously acting as an internal consultant to our business units to refine long‑term strategies. Benefits 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 Responsibilities Internal Strategy & Advisory: Serve as a trusted strategic partner to business unit leaders, driving initiatives to enter new verticals, optimize growth frameworks, and solve critical operational bottlenecks. Value Creation & Deal Execution: Champion a rigorous "Build vs. Buy vs. Partner" framework to maximize enterprise value. Lead the execution of complex transactions, from initial valuation through to due diligence and negotiation. Pipeline Development & Sourcing: Proactively cultivate a pipeline of high‑potential acquisition targets and strategic partnerships across the North American fintech landscape that accelerate Questrade’s ecosystem expansion. Financial Modeling & Commercial Validation: Develop robust financial models and business cases to validate strategic initiatives. Translate complex financial data into clear investment recommendations for the Executive Committee. Cross‑Functional Program Leadership: Orchestrate cross‑functional teams (Product, Legal, Risk, Ops) to drive high‑priority strategic projects from ideation to execution, breaking down silos to ensure rapid delivery. Market Intelligence & Foresight: Monitor the pulse of the fintech industry and macroeconomic trends. Provide the Board with forward‑looking insights on competitive threats, emerging technologies, and disruptive opportunities. Enterprise Strategic Planning: Facilitate the annual and long‑range planning cycles, collaborating with the C‑Suite to define corporate objectives (OKRs) and allocate resources against our highest‑leverage opportunities. Qualifications Have 8–12 years of total experience, with a minimum of 3–5 years in Investment Banking, Management Consulting, or Private Equity. Have experience in Financial Services (FIG) or Fintech. Have a strong understanding of the mechanics of banking and self‑directed investing. Have the ability to bring structure and rigor to ambiguous strategic problems. Have exceptional communication skills. Are a strategic and analytical thinker. Have strong analytical capabilities with an outstanding attention to detail. Have an ability to quickly assimilate large amounts of information; effectively comprehend, synthesize, analyze, structure and facilitate strategic decision making. Have demonstrated experience working with and influencing cross‑functional teams in a collaborative manner. Have solid business acuity, professionalism, and integrity. Are a self‑starter with the ability to work independently and prioritize multiple competing initiatives. Have sophisticated knowledge of Microsoft Office tools, particularly PowerPoint and Excel. Sounds like you? Click below to applyAt Questrade Financial Group of Companies, we are committed to fostering a diverse, inclusive and accessible work environment. We provide accommodations during the recruitment/selection process. Candidates selected for an interview will be contacted directly. #J-18808-Ljbffr