Lead, People Systems

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 $169 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 Team

The People Systems & Operations team builds and runs the systems, workflows, and automations that support every stage of the employee lifecycle at Wealthsimple. We own the design of the processes behind those systems, and we're accountable for their reliability, scale, and integrity. We sit within People & Comms and work closely with Engineering, IT, Legal, Security, and Compliance to make sure our people programs are practical, secure, and actually used.

About the role

Workday is the backbone of how Wealthsimple runs its people programs, and this role keeps it secure, connected, and reliable as we grow. You'll be the team's senior Workday expert across security, configuration, and integrations, owning the work that has to be right: who can see what, how data moves between systems, and how every release lands.

What you'll do

What you bring to the system:

• Model end to end: security groups, domain and business process security policies, role assignments, and proxy and delegation access, with sound judgment about when to use each

• Lead security and data audits using delivered and custom audit reports to analyze access patterns, remediate exceptions, enforce least-privilege access, and uphold segregation of duties

• Own Core HCM and Advanced Comp configuration: including supervisory organizations, staffing models, job and compensation structures, location and cost center hierarchies, and worker data integrity

• Design, build, and maintain inbound and outbound integrations using EIB, Core Connectors, Workday Studio, Orchestration, and Workday web services (SOAP/REST, RaaS)

• Own integration security and reliability: integration system users (ISUs), integration system security groups, credential management, and monitoring and alerting on integration failures

• Manage integrations with downstream and upstream systems, including identity providers, applicant tracking, benefits carriers, finance, and other internal tools, partnering with Engineering and IT on data contracts and error handling

• Lead impact analysis and regression testing for Workday’s biannual feature releases and for internal changes, including how HCM, security, and integration changes ripple through our systems

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

• Partner with Legal, Security, and Compliance teams to make sure People data handling meets our regulatory, privacy, and audit obligations

• 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

• Configure alerts, scheduled reports, and report security so the right data reaches the right people automatically

• Triage and resolve day-to-day system and integration 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, integration monitoring, and report generation

• 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 or Workday Integrations specialist, with demonstrated expertise in system configuration, testing, and implementation

• Workday Pro accreditations or Workday partner certifications in HCM, Security, and/or Integrations

• Hands-on experience building and supporting Workday integrations (EIB, Core Connectors, Studio, web services), plus working knowledge of XML, XSLT, JSON, and API authentication patterns

• Exposure to Workday Extend, Orchestrate, or advanced reporting beyond standard report writer

• Experience applying AI tools to HRIS or People operations work

• Experience supporting audits or controls work (SOC 2, SOX, or equivalent) in a regulated environment is an asset

• 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

• 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

Who you are

• A translator between configuration and business needs: you can explain a security model to an HR partner without losing them

• Detail-oriented, and you write things down so the next person doesn't have to reverse-engineer your work

• Someone who gets to the root cause; a recurring integration failure is a problem to solve, not a ticket to close

• Calm with competing priorities, and good at knowing which ones matter most

• Someone who builds trust with partner teams by being reliable, clear, and easy to work with

• Curious about where automation and AI can take repetitive work off the team's plate

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. The people are one of the best parts of working here: you'll collaborate with incredibly talented, curious, and driven teammates who are deeply committed to doing great work.
*Unlimited paid sick days, Wellness Days and the 90 day away program do not apply to certain roles.

ICYMI

Technology & Innovation at Wealthsimple: We move quickly and build thoughtfully. That means we're always looking for better ways to work — whether that's new tools, AI, or rethinking how we approach a problem. We don't expect you to have all the answers, but we do expect curiosity and a willingness to evolve alongside the products we're building.

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. We also welcome any feedback on how we can better accommodate candidates with accessibility needs.

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. If you have questions about how your data is used, reach out to us.