Wealthsimple

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 $70 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.

The ideal candidate will excel in our dynamic, solutions-oriented environment where deep tax knowledge meets exceptional client experience. They'll join our specialized team that serves as the final escalation point for complex tax matters, transforming challenging situations into opportunities to showcase our technical expertise and human approach to financial services. This role requires someone who can confidently navigate ambiguity, communicate with precision, and find innovative solutions to our most complex tax scenarios.

As a Wealthsimple Tax Level 3 client experience associate, you'll be the definitive resource for resolving our most complex tax inquiries and technical issues. You'll leverage advanced tax knowledge, exceptional problem-solving abilities, and superior communication skills to turn challenging client situations into success stories. Working at the intersection of technical expertise and empathetic support, you'll provide guidance to both clients and internal teams while contributing to our knowledge base and process improvements.

In this role you'll have the opportunity to:

• Resolve complex and escalated tax scenarios that require specialized knowledge or investigation
• Provide authoritative guidance on sophisticated tax situations like investment income reporting and business/self-employment scenarios
• Troubleshoot and document advanced technical issues with our tax software, coordinating with programming and engineering teams when necessary
• Create educational resources that explain complex tax concepts in accessible language for both clients and L1/L2 team members
• Mentor and support L1/L2 agents through knowledge sharing and asynchronous coaching on complex tax scenarios
• Research and interpret CRA/RQ regulations and guidelines to ensure accurate information delivery
• Identify systemic issues and recommend process improvements based on client interactions and feedback patterns
• Develop specialized expertise in particular tax areas to become the team's go-to resource
• Balance thorough investigation with efficient resolution to maintain service levels during high-volume periods
• Maintain detailed documentation of complex cases for future reference and knowledge sharing

What you'll bring:

• 2+ years of customer support experience
• Advanced understanding of Canadian personal taxation concepts, including complex scenarios involving investments, self-employment, foreign income, and cross-border situations
• Demonstrated experience resolving complex technical issues and communicating solutions clearly
• Experience with tax software systems and understanding of how tax calculations are processed digitally
• Strong research skills with the ability to find, interpret, and apply information from CRA/RQ guidelines and tax legislation
• Excellent written communication with the ability to explain complex concepts at various levels of detail based on audience needs
• Proven problem-solving abilities with a systematic approach to troubleshooting
• Experience mentoring or training other team members
• Ability to maintain composure and clarity when addressing high-stress or emotionally charged situations
• Educational mindset: Ability to turn complex tax situations into learning opportunities for clients and team members
• Investigative thoroughness: Commitment to digging beyond surface-level symptoms to identify root causes
• Analytical thinking: Skill in breaking down complex problems into manageable components
• Precise communication: Ability to convey technical concepts with clarity while maintaining empathy
• Calm under pressure: Maintaining a composed, solutions-focused approach during peak tax season and critical incidents
• Systems thinking: Understanding how individual tax issues might reflect broader patterns or software limitations
• Diplomacy: Navigating challenging conversations with clients and internal teams effectively
• Intellectual curiosity: Genuine interest in understanding tax regulations and their practical applications
• Judgment and discretion: Knowing when to escalate to leadership, product teams, or external resources
• Adaptability: Quickly pivoting between different tax scenarios, client needs, and support approaches
• Proactive problem-solving: Identifying potential issues before they affect multiple clients
• Client advocacy: Balancing company policies with genuine care for client outcomes

Nice to have:

• Formal tax training or education (tax preparation courses)
• 3+ years of experience with Canadian tax software (can be personal) or customer support
• Experience with Zendesk, JIRA, and internal knowledge base systems
• Bilingual in English and French to support Québec tax scenarios
• Background in software quality assurance or testing
• Experience working directly with product or engineering teams to resolve technical issues
• Knowledge of tax law changes and the ability to interpret how they affect software functionality
• Understanding of accessibility considerations in digital products

At Wealthsimple Tax, our L3 associates embody our highest standards for technical expertise and client care. We believe that even the most complex tax situations deserve clear, accessible explanations delivered with genuine empathy. Our L3 team serves as both the final resolution point for challenging client scenarios and as knowledge leaders who elevate our entire support ecosystem.

We approach complex problems with curiosity rather than frustration, seeing each difficult case as an opportunity to expand our collective knowledge. Our communication style balances technical precision with human warmth—we're experts who speak in plain language, not jargon. We take the time to understand both the technical details and emotional context of each situation, providing guidance that addresses both the immediate issue and any underlying concerns.

Our L3 team thrives on collaboration, regularly sharing insights across departments to improve our product and processes. We celebrate intellectual generosity, with team members readily sharing their specialized knowledge to help colleagues grow. During tax season's most demanding periods, our L3 specialists become the calm center that both clients and colleagues rely on for steady guidance.

If you're energized by solving the puzzles that others find overwhelming, can explain complex concepts without making people feel intimidated, and find satisfaction in being the person who finally resolves a challenging situation, you'll thrive as a Wealthsimple Tax L3 associate.

Why Wealthsimple?

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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.

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.