Lead, People Systems - Payroll, Absence and Time-Tracking

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.

We're proud of what we've built — and we're just getting started. Read our Culture Manual and learn more about how we work .

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 — the Payroll team owns processing; you own the configuration behind it

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), with sound judgment about when to leverage each as you configure and troubleshoot across domains

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, from testing, documentation, and requirements drafting to ticket triage and report generation, using Anthropic's own tools as part of your daily workflow