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Wealthsimple, Canada's leading financial innovator serving 4+ million Canadians with $155B+ in assets under administration, is seeking a Lead, Learning & Employee Experience to own the end-to-end design and delivery of onboarding, learning programs, and employee events.
In this hands-on facilitation role reporting to the Senior Lead, Program Manager within People Operations, you will design and deliver new employee onboarding (including new leader, intern, and returning-employee cohorts), lead live learning and onboarding sessions regularly for groups of 10–60+ participants in person and remotely, design and oversee company-wide employee events both in-person and remote, build and run learning programs including curriculum design and learning platform management, and measure program effectiveness through feedback loops and metrics to drive continuous iteration.
You'll partner closely with Talent Acquisition, People Systems, Communications, IT, Brand, and departmental leaders. The team is in a build-and-scale phase, modernizing learning delivery, automating onboarding operations, and raising the standard for employee experiences.
Success in the first 6–12 months means new hires becoming productive faster, leaders ready to manage teams from day one, and company-wide events that strengthen connection and clarity on company mission.
Key characteristics: You are energized by facilitation and leading rooms. You have high agency, solving gaps without waiting for permission. You remain unflappable during event execution. You obsess over operational details that create seamless experiences. You're a builder who prefers rebuilding properly to patching. You're comfortable with ambiguity and shifting priorities. You genuinely care how it feels to be new, learning, or being led.
Wealthsimple offers top-tier health benefits and life insurance, long-term group savings with employer match, 20 vacation days plus 4 wellness days and unlimited sick/mental health days, 90 days per year to work outside Canada, employee resource groups (Rainbow, Women of WS, Black at WS), and a hybrid team of 1,500+ talented, curious, driven employees across North America.
REQUIREMENTS:
- 5+ years designing, delivering, and running onboarding, learning, or employee experience programs end-to-end (not executing someone else's design)
- Demonstrated excellence as a facilitator: regular live session leadership for mixed and senior audiences, in-person and remote, with ability to hold a room, adapt in the moment, and land outcomes
- Hands-on experience planning and producing employee events from concept to delivery, including experience design, budgets, vendors, communications, logistics, with real accountability for results
- Instructional design and curriculum-building experience: ability to turn business needs into programs people learn from, and build in a learning platform yourself
- Data-driven approach: building measurement from the start, using feedback and metrics to guide changes, and good judgment with AI tools for content design and program operations
NICE TO HAVE:
- Hands-on experience building in a learning management system (Docebo or similar)
- Experience producing multi-day employee events for 200+ attendees
- Formal instructional design or facilitation training
