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 Wealthsimplers 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 at it

In 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

Benefits

Retirement savings matching plan through Wealthsimple Work

Company equity for full-time employees

Access to Premium Client perks, including personal finance learning & advice and a boosted interest rate on deposits

Paid parental leave (6 months topped up to 100% of salary)

20 vacation days per year

90 Days Away program

Top-tier health benefits

Life & disability insurance

Generous sick and mental health days

Up to $5,000 per year for mental health supports

Employee resource plan including services like RMT, psychology, and physiotherapy

Gender Affiliation benefits

Up to $1,500 per year for professional development

Up to $1,500 per year for wellness and home office expenses

Employee resource groups

Social impact hours

Requirements

A data-driven approach:



you build measurement in from the start and let feedback and metrics decide what changes.

You use valuable judgement when leveraging AI tools to speed up content design, maintenance and program operations

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

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

Human first. You genuinely care how it feels to be new, to be learning, or to be led

Energized by a room. Facilitating is the part of your week you look forward to, and it shows

Unflappable on event day. Things go sideways, you solve them quietly, and the room never knows

Comfortable with ambiguity and shifting priorities, and able to keep momentum without waiting to be told

High agency. You see a gap and close it, and you’d rather ask forgiveness than permission

Detail‑obsessed about the operational backbone. You know a great experience is logistics done invisibly well

A builder, not a maintainer. You’d rather rebuild something properly than keep patching it

Experience producing multi‑day employee events for 200+ attendees

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

Formal instructional design or facilitation training

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📌 Learning & Employee Experience Lead (Manitoba)
🏢 Wealthsimple
📍 Manitoba