Lead, People Systems in Winnipeg

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 $155 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.

About the People Systems & Operations Team: The People Systems and Operations team builds and operates the systems, workflows, and automations the business runs on. We manage every stage of the employee lifecycle and own the design and optimization of the processes behind it. We're accountable for the reliability, scale, and integrity of our People systems.

What you bring to the system:

• Configure and maintain Payroll: pay components, earnings and deductions, pay groups, period schedules, and payroll-related business processes.
• Configure and maintain Absence: time-off plans, accrual rules, eligibility criteria, and leave types.
• Configure and maintain Time Tracking: time entry templates, validations, work calendars, and overtime calculations.
• Configure and maintain Core HCM foundations: supervisory organizations, staffing models, job profiles and job/compensation structures, custom organizations, and worker data integrity.
• Support annual and recurring People cycles in Workday, including compensation reviews, open enrollment configuration, and org restructures (mass supervisory org changes and job catalog updates).
• Design, build, and maintain business process definitions in both domains, including condition rules, calculated fields, custom validations, routing and approval logic, and notifications.
• Partner with the Payroll team to troubleshoot configuration-driven payroll issues, including gross-to-net discrepancies, retro calculations, and off-cycle errors.
• Bring a strong command of the Workday security model: role-based, user-based, and intersection security groups, domain security policies, business process security policies, and integration system users (ISUs).
• Support security and data audits in partnership with the broader team, using Workday delivered and custom audit reports to analyze access patterns, remediate exceptions, and uphold segregation of duties.
• Perform impact analysis before changes ship, including how HCM and security changes ripple into payroll, absence, and time data.

What you bring to the business:

• Translate business requirements from our internal partners into scalable system design, and document configuration decisions as you go.
• Build trusted relationships with partner teams, acting as a translator between technical configuration and business needs.
• Support change management for system updates and new functionality: communicate what's changing and why, prepare documentation and enablement materials, and make sure changes land well with the people who use them.
• Build and maintain advanced, matrix, and composite reports and dashboards; support mass data changes via EIB.
• Configure alerts, scheduled reports, and report security so the right data reaches the right people automatically.
• Triage and resolve day-to-day system issues, getting to root cause rather than patching symptoms.
• Actively look for where AI and automation can strengthen how People Systems works.
• Drive process automation and optimization opportunities with the broader People team and partner functions.

Qualifications:

• 7+ years of experience as a Workday Business Systems Analyst, with demonstrated expertise in system configuration, testing, and implementation.
• Workday Pro accreditations or Workday partner certifications in HCM, Payroll, Absence, Time Tracking.
• Exposure to Workday Prism Analytics, Extend, or advanced reporting beyond standard report writer.
• Experience applying AI tools to HRIS or People operations work, or strong interest in building that muscle.
• Have deep hands-on working knowledge of Workday Payroll, Absence, and Time Tracking (PATT) configuration and design, business process configuration, and Security.
• Have hands-on working knowledge of Workday Core HCM.
• Have worked in a fast-paced, high-growth environment and know how to flex between roles.
• Possess strong technical skills including understanding of Workday architecture, security models, and integration methodologies.
• Have experience with full lifecycle Workday implementations and/or significant module expansions.
• Are intellectually curious, you ask "why" before "how," explore root causes rather than symptoms, and stay current on Workday and adjacent HR tech.
• Approach problems with creativity, comfortable looking past the standard or obvious solution to find an answer that actually fits the business.
• Treat HR data security and privacy as a non-negotiable foundation in everything you build and maintain.
• Excel at building relationships and communicating effectively with technical and non-technical stakeholders at all levels.
• Are detail-oriented with strong documentation skills and a commitment to process excellence.
• Have a track record of managing multiple competing priorities, with a bias toward flexibility and impact.
• Have a collaborative mindset and willingness to pick up slack even if it goes outside your job description.

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.

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.

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.