Lead, Learning

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.

As Lead, Learning & Employee Experience, you own the experiences that shape how it feels to join, learn and grow at Wealthsimple: our onboarding and learning programs, and the employee events that bring Wealthsimple rs together in person and remotely. You design, deliver and run all of it, end to end. This is a hands-on facilitation role reporting to our Senior Lead, Program Manager within People Operations, so you will be in front of a room regularly and often, and you will be exceptional  your first 6-12 months, success looks like new hires getting productive faster, leaders ready to run a team well from their first quarter, and company-wide events that send people back to their teams more connected and clearer on what we're building and why.

Our Employee Experience team sits within People Operations and owns the experiences that define life at Wealthsimple: new employee onboarding, learning and development, mandatory and compliance training, and the company-wide events that bring us together. We're a small, high-autonomy team that partners closely with Talent Acquisition, People Systems, Communications, IT, Brand and departmental leaders across the business. We're in a build-and-scale phase, modernizing how we deliver learning, automating the operational backbone of onboarding, and raising the standard for our employee events and experiences.

• Own new employee onboarding end to end. Design, deliver and run every cohort, from pre-boarding communications through to the live sessions, and build tailored paths with department leaders. Same for new leader, intern and returning-employee onboarding.

• Facilitate, regularly and often. You will lead live learning and onboarding sessions for groups of ten to sixty-plus, in person and remotely. This is core to the job, not an occasional add-on, so you need to love it and be great at it.

• Design, develop and oversee our key employee events, delivered both in person and remotely and thinking about how these fit together in a cohesive way. You own the plan and the day: experience and agenda design, workback, budgets and vendors, executive briefings, communications, registration and production.

• Build and run our learning programs. Design the curriculum, from leadership foundations to mandatory and compliance training, build it in our learning platform yourself, and own the logistics that keep it running.

• Measure what you build and bring people with you. Create the feedback loops that show whether a program is working, and keep Talent, Communications, IT, Brand and senior leaders aligned so it lands. You ship, learn, and iterate - no program you own is ever delivered the same way twice.

• 5+ years designing, delivering and running onboarding, learning or employee experience programs, owning them end to end rather than executing someone else’s design.

• Demonstrated excellence as a facilitator: you've led live sessions regularly for mixed and senior audiences, in person and remotely, and can speak to how you hold a room, adapt in the moment and land the outcome.

• Hands-on experience planning and producing employee events from concept to delivery, covering experience design, budgets, vendors, communications and logistics, with real accountability for the result.

• Instructional design and curriculum-building experience: you can turn a business need into a program people actually learn from, and build it in a learning platform yourself.

• A data-driven approach: you build measurement in from the start and let feedback and metrics decide what changes. You use good judgement when leveraging AI tools to speed up content design, maintenance and program operations.

• Hands-on experience building in a learning management system (Docebo or similar)

• Experience producing multi-day employee events for 200+ attendees

• Formal…