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Wealthsimple is on a mission to help everyone achieve financial freedom by reimagining what it means to manage your money. Using smart technology, we take financial services that are often confusing and expensive and make them transparent and low-cost for everyone. We’re the largest fintech company in Canada, with 3+ million users who trust us with more than $100 billion in assets. And we’re just getting started.
We’re looking for someonewho thinks big, sweats the small stuff and keeps things simple. You’ll join a high-bar, fast-paced team where people are trusted to own their work, communicate openly, and ship things that improve our clients’ lives. Collaboration, humility, and an obsession over quality are how we get stuff done.
About the Commercial Strategy & Operations Team:
The Commercial Strategy & Operations team’s purpose is to serve as the strategic engine of the Commercial organization. By integrating robust systems, high-impact enablement, scalable lead management, and streamlined revenue operations, we bridge the gap between strategy and daily execution. Working cross-functionally, we align teams, tools, and insights to drive predictable, sustainable growth.
This Role:
The Commercial Strategy & Operations team is seeking a technical and strategic Manager, AI & Agentic Workflows to lead the evolution of our Commercial team. You will be responsible for designing, deploying, and optimizing autonomous AI agents and multi-agent systems that automate complex, end-to-end workflows. As our Manager, AI & Agentic Workflows, you aren’t just automating tasks—you are architecting the future of how we work. This role will sit on the Commercial Strategy & Operations team and support growth across the Commercial, Marketing, and Customer Experience teams.
Unlike traditional automation, you will focus on agentic patterns: systems capable of reasoning, using tools (APIs), and self-correcting to achieve high-level business objectives with minimal human intervention. Your work will directly reduce manual operational effort and unlock faster, more consistent execution across the Commercial organization. In your first 6 months, you will have established an AI & Agentic Roadmap and have designed and deployed 2-3 agentic workflows that meaningfully reduce manual effort across teams.
In this role you’ll have the opportunity to:
- Be a true maker-owner: You will be the owner of the AI & agentic stack. You will take full ownership of the end-to-end roadmap and bridge the gap between 'AI potential' and 'operational reality' by shipping agents that act, learn, and resolve complex workflows independently.
- Architect Agentic Workflows: Design, deploy, and iterate on multi-agent systems to handle complex commercial tasks like customer segmentation, lead qualification, lead routing, quota planning, enablement, and proactive sales process alerts.
- Orchestrate the Commercial Stack: Develop deep, bi-directional integrations between AI agents and our core toolkit (Salesforce, Slack, Gong, Braze, etc.). You will ensure our stack isn't just a group of disconnected apps, but a unified, agent-driven nervous system.
- Prompt Engineering & Tuning: Develop and iterate on sophisticated system prompts to ensure agent outputs are accurate, brand-compliant, and grounded in company data.
- Establish Human-AI Collaboration: Design elegant "Human-in-the-Loop" (HITL) protocols. You will build the logic that allows agents to handle high-volume complexity while identifying high-stakes nuances that require a seamless hand-off to our human experts.
- Continuously Monitor Performance: Establish KPIs for AI agents (e.g., "Success Rate of Autonomous Resolution," "Time Saved per Workflow") and continuously optimize for cost and latency.
- Fortify Governance & Safety: Implement guardrails to ensure AI agents operate within ethical boundaries and maintain data privacy standards.
What you’ll bring:
- 5+ years of experience in process re-design, business transformation, or workflow optimization, with a proven track record of influencing senior stakeholders and navigating ambiguity.
- Strong experience with Python and AI orchestration libraries. Deep understanding of LLM APIs.
- Ability to map a manual, 10-step human process into a logical, automated sequence of tool calls and reasoning steps.
- Understanding of the lead-to-revenue lifecycle, sales processes, and customer journey maps.
- Demonstrated track record managing ambiguity well and driving impact in an environment where priorities and direction can evolve quickly. You should have a positive can-do attitude and be adaptable to evolving business goals.
- Excellent interpersonal and communication skills and an ability to work cross-functionally with a wide range of stakeholders
- Exposure to AI voice chat is a plus.
Compensation & Equity
🤑 Base salary range: For this role, candidates located in Canada can expect a base salary range of CAD $116,000 - $145,000. Actual compensation is determined based on skills, experience, and role level. Exceptional candidates may be considered above the top of the range, and pay can increase quickly for those who make a big impact in the role.
🚀 Total compensation: In addition to base salary, this role includes equity compensation. We use clear job levels and market-based salary bands to ensure compensation is fair and consistent across the company.
Why Wealthsimple?
🌸 Top-tier health benefits and life insurance
📈 Long-term group savings with employer match using our Wealthsimple for Business platform
🌴 20 vacation days + 4 wellness days per year, and unlimited sick and mental health days
✈️ 90 days away program: Employees can work outside of Canada for up to 90 days per calendar year
👥 A wide variety of peer and company-led Employee Resources Groups (e.g., Rainbow, Women of Wealthsimple, Black @ WS)
🌎 We’re a remote first team with over 1,500 employees across North America - and one of the best things about working here is the people. You’ll be collaborating with incredibly talented, curious, and driven teammates who care deeply about doing great work.
Be a part of our Canadian success story and help shape the financial future of millions.
Read our Culture Manual and learn more about how we work.
Technology & Innovation at Wealthsimple
We believe the future belongs to those who innovate boldly. At Wealthsimple, every team member is expected to lean into new technologies, including AI, and tooling to rethink how we work, solve problems faster, and create even greater value. We're looking for people who are not just comfortable with change but energized by it. Our commitment is to build a company that evolves at the pace of the world around us, and we want you to help lead that future.
DEI Statement
At Wealthsimple, we are building products for a diverse world and we need a diverse team to do that successfully. We strongly encourage applications from everyone regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status.
Accessibility Statement
Wealthsimple provides an accessible candidate experience. If you need any accommodations or adjustments throughout the interview process and beyond, please let us know, and we will work with you to provide the necessary support and make reasonable accommodations to facilitate your participation. We are continuously working to improve our accessibility practices and welcome any feedback or suggestions on how we can better accommodate candidates with accessibility needs.
At Wealthsimple, we want interviews to feel like genuine conversations. To support this, we use AI transcription during recruiter interviews. This allows recruiters to be fully engaged, ask thoughtful follow-up questions, and ensure your experiences are captured accurately. You’ll always have the choice to opt in or out before we begin.
BR, CA + 3 more
