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Senior Specialist, Payroll

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.


Reporting to the Payroll Manager, the Senior Specialist, Payroll will be responsible for ensuring compliant and accurate payroll operations for Canada, including Quebec, and the US. This role provides oversight of end-to-end payroll processes, including benefits operations and provides guidance and review to the Payroll Specialists. It is an opportunity to refine scalable workflows and ensure smooth and timely administration.


In this role, you will have the opportunity to:
  • Review and oversee the end-to-end payroll process, including onboarding, status changes, leave management (e.g., pregnancy, parental, and disability), and offboarding, ensuring accuracy and compliance.
  • Serve as a point of escalation for more complex payroll transactions, providing advice on best practices and resolving issues efficiently.
  • Collaborate with the Payroll Specialists and HR Operation Specialists to streamline workflows, ensuring smooth information flow and accurate data in our HRIS (Workday).
  • Build strong relationships with payroll providers, troubleshooting issues like amending ROEs, handling special pay runs, and resolving time-sensitive payroll matters.
  • Respond to CRA or IRS inquiries, and other payroll partners.
  • Support payroll-related aspects of group benefits and retirement programs (GRSP and 401K) ensuring accurate deductions, contributions, and compliance.
  • Provide the business with payroll expertise and support on ongoing projects. 


We're looking for someone who brings:
  • Payroll certification (PCP or PLP).
  • 7+ years of payroll experience, including multi-province (Quebec) and US payroll, with experience reviewing and ensuring the accuracy of others’ work.
  • A strong understanding of payroll compliance and legislation across Canada and the US.
  • Proven initiative and accountability for delivering high-quality work, with a focus on continuous improvement.
  • Exceptional time management skills, with the ability to meet deadlines and manage priorities effectively.
  • Excellent verbal and written communication skills, with the ability to explain complex payroll matters clearly and concisely.


Please apply by January 24th 2025.


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.

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What You Should Know About Senior Specialist, Payroll, Wealthsimple

Are you ready to take your payroll expertise to new heights? Wealthsimple, Canada's largest fintech company, is excited to welcome a Senior Specialist, Payroll to our vibrant team in Toronto. At Wealthsimple, we’re all about making financial management uncomplicated and accessible, and as part of our mission, you will play a crucial role in overseeing the payroll operations for Canada and the U.S. Your experience will shine as you navigate the end-to-end payroll processes, ensuring compliance and accuracy at every step—from onboarding to offboarding and everything in between. You will be the go-to person for resolving complex payroll matters, guiding our Payroll Specialists, and collaborating seamlessly with HR teams to enhance workflow efficiencies. Your role will involve building strong relationships with payroll providers and offering your expertise on group benefits and retirement programs. If you have over 7 years of payroll experience, combined with a solid understanding of multi-province and US payroll legislation, we want to hear from you! With a focus on continuous improvement, you’ll thrive in a culture that values high-quality work and inclusive collaboration. Wealthsimple offers a competitive salary, comprehensive health benefits, and opportunities for professional development. If you love financial technology and want to make a tangible impact, this is your chance to be part of an inspiring team that is shaping the financial future for millions. Join us and let’s grow together!

Frequently Asked Questions (FAQs) for Senior Specialist, Payroll Role at Wealthsimple
What are the key responsibilities of the Senior Specialist, Payroll role at Wealthsimple?

As a Senior Specialist, Payroll at Wealthsimple, you'll be responsible for overseeing the end-to-end payroll process in Canada and the U.S. This includes handling onboarding, managing leave requests, and ensuring compliance with payroll legislation. You'll also provide guidance to Payroll Specialists, collaborate with HR staff to optimize workflows, and serve as a point of escalation for complex payroll inquiries. Building relationships with payroll providers and supporting benefits administration are key components of this role, ensuring that everything is accurate and timely.

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What qualifications are needed to apply for the Senior Specialist, Payroll position at Wealthsimple?

To apply for the Senior Specialist, Payroll position at Wealthsimple, candidates should possess payroll certification (PCP or PLP) and have at least 7 years of experience in payroll, specifically with multi-province (including Quebec) and U.S. payroll. A strong understanding of payroll compliance and legislation is crucial, along with excellent communication skills and a proactive approach to continuous improvement. If you're meticulous and can manage time effectively, you'll be a great fit!

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How does Wealthsimple ensure payroll compliance and accuracy for its employees?

Wealthsimple ensures payroll compliance and accuracy through a rigorous oversight process in which the Senior Specialist, Payroll reviews payroll processes and transactions. You will implement scalable workflows, manage leave requests, and respond to CRA or IRS inquiries. Collaborating with Payroll and HR teams helps maintain accurate data in the HRIS, ensuring that employees' payroll matters are handled promptly and efficiently.

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What tools and systems do Payroll Specialists at Wealthsimple use?

At Wealthsimple, Payroll Specialists use Workday as their Human Resource Information System (HRIS) to streamline payroll workflows and manage employee data. This platform allows for efficient handling of onboarding, pay processing, and compliance checks. As a Senior Specialist, you'll collaborate closely with Payroll and HR Operation Specialists to ensure data accuracy and effective information flow through this system.

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What kind of company culture can one expect while working as a Senior Specialist, Payroll at Wealthsimple?

Working at Wealthsimple as a Senior Specialist, Payroll means joining a remote-first team that values inclusion, collaboration, and continuous growth. The company encourages open communication and offers various Employee Resource Groups to support diversity and well-being. Employees enjoy competitive salaries, generous vacation allowances, and mental wellness days, all within an environment that promotes innovation and accountability. You'll be part of a team that is passionate about transforming the financial landscape for everyone.

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Common Interview Questions for Senior Specialist, Payroll
How do you ensure the accuracy of payroll in a multi-province environment like Canada?

To ensure payroll accuracy in a multi-province environment, I carefully keep updated on the latest payroll legislation and tax codes for each province, especially for Quebec, which has unique requirements. Implementing rigorous checks during the payroll processing stages and collaborating with HR to verify employee data also helps maintain accuracy. Furthermore, regular audits and continuous improvement practices play a crucial role in identifying areas for enhancement.

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Can you describe your experience with payroll systems, particularly Workday?

I have extensive experience with payroll systems, specifically Workday. I’ve managed end-to-end payroll processes within Workday, from employee onboarding to managing offboarding, ensuring that data flows seamlessly through the system. Regularly leveraging its reporting features has helped me monitor data for compliance and accuracy. Proficient with workarounds and custom reports, I can extract valuable insights to refine payroll workflows further.

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How do you handle complex payroll inquiries from employees or tax authorities?

When dealing with complex payroll inquiries, I first approach the situation with empathy, ensuring that the employee feels heard. I gather all relevant information and review the transaction details before responding. If necessary, I collaborate with our payroll providers or tax authorities to resolve the issue efficiently. Keeping thorough documentation helps maintain transparency and serves as a reference for similar issues in the future.

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What strategies do you use to stay compliant with payroll legislation?

To stay compliant with payroll legislation, I prioritize continuous education by attending workshops, webinars, and networking sessions within the payroll field. I also subscribe to relevant publications that highlight changes in legislation. Additionally, I foster a strong relationship with legal and compliance teams within the organization to ensure that we preemptively address upcoming changes in regulations impacting payroll.

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How do you approach collaboration with HR to streamline payroll processes?

Collaboration with HR is essential for streamlining payroll processes. I arrange regular meetings with HR specialists to discuss workflows, assess areas that can be improved, and ensure we’re aligned on employee data accuracy. Streamlining communication and leveraging technology to share updates and documents in real-time has also proven effective in enhancing collaboration and ensuring timely resolution of issues.

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Describe a time when you identified a significant payroll error and what steps you took to resolve it.

In a previous role, I identified a discrepancy in tax deductions due to a software glitch. Upon noticing the error, I immediately flagged it for review and conducted a thorough audit of the payroll data to understand the scope. After verifying the affected employee records, I coordinated with our payroll provider to rectify the deductions and communicated the update to all impacted employees, ensuring clarity and transparency throughout the process.

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What methods do you use to improve payroll efficiency?

To improve payroll efficiency, I consistently analyze our existing workflows and identify bottlenecks. Implementing technology solutions, such as automated payroll processing features in our HRIS, has greatly improved efficiency. I also champion a culture of continuous feedback and enhance training for Payroll Specialists to equip them with the knowledge to manage tasks with greater speed and accuracy. Regularly measuring our KPIs also helps pinpoint areas for improvement.

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How do you ensure data privacy and security when handling payroll information?

Ensuring data privacy and security is crucial within payroll operations. I adhere to best practices by implementing strict access controls to sensitive payroll data within our systems. Regular data audits are performed, and I educate the payroll team on data handling protocols to minimize risk. Lastly, I collaborate with IT for regular system updates and utilize encryption whenever possible to safeguard payroll information.

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Can you explain your approach to managing payroll during high-volume times, such as year-end?

During high-volume payroll periods, such as year-end, I begin preparation well in advance. This includes creating a detailed schedule with key deadlines and ensuring that all team members are informed and prepared. Leveraging payroll software features to process bulk transactions efficiently is vital, while proactive communication with staff ensures they are on the same page. Post-processing audits and reconciliations help catch any discrepancies early and maintain smooth operations.

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What motivates you to work in payroll, and specifically at Wealthsimple?

My motivation for working in payroll stems from a passion for supporting employees and contributing to an organization’s success via accurate financial management. At Wealthsimple, the culture of innovation and commitment to making things simple resonates with my professional ethos. I want to be part of a team that not only values and respects its employees but also plays a role in transforming financial services for everyone. Knowing my work has a direct impact on someone’s financial peace gives me a profound sense of purpose.

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