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SPECIALIST CYBER DIPLOMACY & GOVERNANCE (BUSINESS STRATEGY & PLANNING)
City of Toronto
Toronto, ON
Division & Section: Toronto Cyber Security, Cyber Operations

Wealthsimple Technologies

Lead, Learning & Employee Experience

Remote, Canada

Remote

$116,000 to $145,000 CAD / year · Full-time

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Job details

Pay: $116,000 to $145,000 CAD / year
Job type: Full-time
Workplace: Remote
Experience: 5+ years designing, delivering and running onboarding, learning or employee experience programs, owning them end to end rather than executing someone else’s design.
Posting language: English
Posted: Oct 29, 2026

Original job description

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 role

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.

About the team

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.

What you’ll do

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.

Skills you'll bring

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.

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

Who you are

Energized by a room. Facilitating is the part of your week you look forward to, and it shows.
High agency. You see a gap and close it, and you’d rather ask forgiveness than permission.
Unflappable on event day. Things go sideways, you solve them quietly, and the room never knows.
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.
Comfortable with ambiguity and shifting priorities, and able to keep momentum without waiting to be told.
Human first. You genuinely care how it feels to be new, to be learning, or to be led.

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.

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More about this job

Responsibilities

You will own the end-to-end design and delivery of onboarding, learning programs, and employee events for both remote and in-person settings. This role involves facilitating sessions, managing budgets and vendors, and iterating on programs based on feedback and performance metrics.

Requirements

Candidates must have 5+ years of experience in onboarding, learning, or employee experience programs with a strong background in facilitation. You should be proficient in instructional design, event production, and using data to measure and improve program effectiveness.

Skills

Onboarding
Learning and development
Employee experience
Facilitation
Instructional design
Curriculum development
Event planning
Project management
Data-driven decision making
Stakeholder management
Budget management
Vendor management
Communication
Leadership development
Compliance training
Learning management systems

Benefits

Health benefits
Life insurance
Long-term group savings with employer match
20 vacation days
4 wellness days
Unlimited sick days
Unlimited mental health days
90 days away program
Equity compensation

Visa sponsorship

Not detected in the job text

Keywords

Onboarding
Learning and Development
Employee Experience
Facilitation
Instructional Design
Curriculum Building
Event Management
People Operations
Docebo
LMS
Data-driven
Project Management
Hybrid Work
Leadership Foundations
Compliance Training
Budgeting
Vendor Relations
AI Tools
Employee Engagement
Performance Metrics
Strategic Planning
Communication
Stakeholder Alignment
Logistics
Program Management

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