Senior Program Manager, Brokerage Automation

Build something people love

Wealthsimple is Canada’s leading financial innovator. The company offers a full suite of simple, sophisticated financial products across managed investing, do-it-yourself trading, cryptocurrency, tax filing, spending and saving. Wealthsimple currently serves more than 4 million Canadians and holds over $125 billion in assets under administration. The company was founded in 2014 by a team of financial experts and technology entrepreneurs, and is headquartered in Toronto, Canada.

We're proud of what we've built — and we're just getting started. Read our Culture Manual and learn more about how we work .

As a Senior Program Manager, Brokerage Automation , you will act as the vital bridge between Wealthsimple’s Brokerage functions and our technical teams (Engineering and AI Builders). Reporting to the VP, Head of Capital Markets & COO, you will not just manage tasks, but strategically architect, prioritize, and translate business operational needs into technical requirements, ensuring large-scale transformation initiatives are executed flawlessly.

Your primary focus will be driving holistic workflow improvements and technical integrations that directly impact back-office operations. You are the translator who understands enough about how AI and systems are built to have deeply credible conversations with engineers, while keeping a sharp eye on project tracking, impact, and timelines.

What You'll Do

• Drive operations transformatio n: Reimagining workflows across the Brokerage functions. Develop a clear roadmap for optimizing your processes in these functions, ensuring alignment with leadership and organizational priorities.

• Bridge Business and Tech: Act as the primary liaison between Brokerage stakeholders and technical teams (Engineering and AI builders). Translate complex back-office operational needs into clear, actionable technical requirements.

• Be a true maker-owner: Lead the strategy to transform the back office through automation while using AI agents and tooling where possible. Develop metrics and dashboards to create visibility into the impact of this transformation. Push the teams to think outside of the box and what has always been done to find new, exciting and highly efficient ways to do things.

• Drive Program & Project Management: Own the end-to-end lifecycle of transformation initiatives. Establish robust project tracking, manage roadmaps, define milestones, and hold cross-functional teams accountable to deadlines.

• Prioritize and Track Impact: Evaluate potential initiatives based on business impact, technical feasibility, and resource constraints. Design mechanisms to track, measure, and report on the ROI and operational efficiency of deployed solutions.

• Architect Solutions & Translate Work: Analyze existing back-office process gaps and collaborate with technical teams to design scalable automation and AI-driven workflows. Ensure technical constraints and trade-offs are clearly communicated to business leadership.

• Influence and Align Stakeholders: Partner with senior leaders across Brokerage, and engineering to build consensus on priorities, secure resources, and align diverse teams toward common strategic goals.

• Build the Playbook: Develop and maintain program documentation, operational frameworks, and change-management playbooks to ensure smooth adoption of new technologies across the broader Brokerage functions

Skills You Bring

• Program Management Excellence: 5+ years of experience leading complex, cross-functional business transformation or technical program management (TPM) initiatives, ideally within a fast-paced fintech or financial services environment.

• Technical Credibility (AI & Engineering): A strong conceptual understanding of how modern software and AI systems are built. You don't need to write the code, but you must be able to navigate technical discussions with engineers, understand technical trade-offs, confidently challenge assumptions and suggest new ways of operating and tackling problems.

• Back-Office Operational Acumen: Deep familiarity with operations and workflow optimization environments. You understand how the business functions and how technology can scale those operations.

• Exceptional Communication & Translation: A proven track record of translating complex technical concepts for business stakeholders, and vice versa. You can convey strategy clearly to senior executives and precision requirements to developer teams.

• Data-Driven Prioritization: Able to look at the full picture not just one project at a time. Find efficiencies across the whole org and leverage efficiencies across teams

• Strategic Influence & Ambiguity Navigation: Demonstrated ability to drive alignment across distinct organizational pillars (e.g., Brokerage vs. Engineering), manage competing priorities, and bring structure to ambiguous, fast-moving situations.

Why Wealthsimple?

Top-tier health benefits and life insurance

Long-term group savings with employer match, through Wealthsimple for Business

20 vacation days, 4 wellness days, and unlimited sick and mental health days per year

✈️ 90 days away: work outside Canada for up to 90 days per year

Employee resource groups, including Rainbow (2SLGBTQ), Women of WS, and Black at WS

We are a hybrid team with over 1,500 employees across North America. The people are one of the best parts of working here: you'll collaborate with incredibly talented, curious, and driven teammates who are deeply committed to doing great work.

ICYMI

Technology & Innovation at Wealthsimple: We move quickly and build thoughtfully. That means we're always looking for better ways to work — whether that's new tools, AI, or rethinking how we approach a problem. We don't expect you to have all the answers, but we do expect curiosity and a willingness to evolve alongside the products we're building.

Inclusion Statement: We're building products for a diverse world, and we need a diverse team to do it well. We strongly encourage applications from everyone, regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status.

Accessibility Statement: We're committed to an accessible hiring experience. If you need any accommodations throughout the interview process, please let us know — we'll work with you to make sure you have what you need. We also welcome any feedback on how we can better accommodate candidates with accessibility needs.

AI in Hiring: We may use artificial intelligence (AI) tools to support parts of our hiring process, such as reviewing applications, analyzing resumes, or assessing responses. These tools assist our team but don't replace human judgment – all final hiring decisions are made by people. If you have questions about how your data is used, reach out to us.