Director, Client Experience Operations

Your career is an investment that grows over time!

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, opaque and expensive and make them transparent and low-cost for everyone. We’re the largest fintech company in Canada, with over 4 million users who trust us with more than $50 billion in assets.

Our teams ship often and make an impact with groundbreaking ideas. We're looking for talented people who keep it simple and value collaboration and humility as we continue to create inclusive and high-performing teams where people can be inspired to do their best work.

About the Role

We’re looking for a visionary, execution-driven Director of Customer Experience Operations to define and lead the strategy for how we scale, optimize, and innovate the systems, tools, and processes that power our customer experience. This is a high-impact, cross-functional leadership role with both strategic and operational scope. You’ll serve as a thought leader and strategic partner across CXO and R&D, setting the direction for how we leverage technology, AI, knowledge, and process excellence to enable high-quality, efficient, and scalable customer support. You’ll lead a team to drive the evolution of our core CX systems, oversee the design and implementation of AI solutions (e.g., chatbots and automation), evolve our knowledge and content strategy, ensure operational readiness for product releases, and champion continuous improvement across workflows. You’ll build and lead a small but mighty team and have a direct hand in shaping the future of the customer experience function.

• Strategic Leadership & Vision
• Set the strategic vision for how systems, AI, knowledge, and workflow optimization work together to elevate CX and operational performance.
• Act as a thought leader across the company for how we modernize and scale our CX ecosystem.
• Partner closely with leadership to align CX systems and enablement strategy with broader client experience goals.
• Systems Strategy & Optimization
• Own the roadmap, design, and administration of CX systems (e.g., Zendesk, Five9)
• Identify and drive system enhancements, automations, and integrations that improve team efficiency and customer outcomes.
• AI & Automation for Customer Support
• Lead the strategy and execution of AI/automation initiatives — including chatbots, self-service flows, and intelligent routing.
• Partner with R&D teams to ensure AI solutions are data-informed, human-centered, and continuously optimized.
• Stay ahead of emerging AI trends and assess applicability to our customer operations.
• Content & Knowledge Management
• Own the internal and external client experience knowledge strategy, ensuring content is accessible, accurate, AI-optimized, and effectively supports customers and frontline teams.
• Define content governance frameworks and evolve tools to support proactive knowledge sharing.
• Drive alignment between content, product updates, and support readiness.
• Release Readiness & Change Management
• Oversee cross-functional processes to prepare CX teams for new product and feature launches.
• Ensure frontline teams are equipped with the right knowledge, tools, and processes to support change effectively.
• Act as a key connector between Product, CX, and Enablement teams to ensure tight coordination.
• Workflow Optimization & Process Improvement
• Oversee strategic initiatives to optimize and scale customer support workflows.
• Use data to identify inefficiencies, reduce operational friction, and improve team and customer experience.
• Embed a culture of continuous improvement and cross-functional collaboration.

• 8–10+ years of experience in customer experience, business systems, enablement, or CX strategy roles, with leadership experience in scaling operations or tools.
• Passion for creating efficient, high-quality customer experiences and enabling others to do their best work.
• Demonstrated ability to set strategic direction and deliver cross-functional programs that transform how teams work and customers are served.
• Familiarity with deploying AI/automation use cases in customer-facing or support workflows.
• Strong communication and stakeholder management skills — capable of influencing across departments and levels.

Why Wealthsimple?

🤑 Competitive salary with top-tier health benefits and life insurance

📈 Retirement savings matching plan using Wealthsimple Work

🌴 20 vacation days per year and unlimited sick and mental health days

📚 Up to $1,500 per year towards wellness and professional development budgets respectively 

🛫 90 days away program: Employees can work internationally in eligible countries for up to 90 days per calendar year 

🌎 A wide variety of peer and company-led Employee Resource Groups (ie. Rainbow, Women of Wealthsimple, Black @ WS)

💖 Company-wide wellness days off scheduled throughout the year

We’re a remote-first team, with over 1,000 employees coast to coast in North America. Be a part of our Canadian success story and help shape the financial future of millions — join us!

Read our Culture Manual and learn more about how we work.

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.