---
title: 'Lead, Learning & Employee Experience at Wealthsimple Technologies'
canonical: 'https://feeny.ai/job/lead-learning-employee-experience-wealthsimple-technologies-canada-aw72gc8y95vj'
type: 'job'
last_seen: '2026-10-30'
---

# Lead, Learning & Employee Experience at Wealthsimple Technologies

- **Company:** Wealthsimple Technologies
- **Location:** Canada
- **Compensation:** $116k–$145k
- **Employment:** full-time
- **Work type:** remote
- **Posted:** 2026-10-29
- **Last confirmed live:** 2026-10-30
- **Apply:** https://jobs.ashbyhq.com/wealthsimple/1f61607b-85f9-440b-8345-64889add3bb8

## 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](https://www.wealthsimple.com/en-ca/culture) and learn more about [how we work](https://www.wealthsimple.com/en-ca/careers).

## 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.

## About Wealthsimple Technologies

## Company Overview
- **One-liner**: Wealthsimple is a Canadian financial technology company that offers commission-free trading, automated investing, banking, and advisory services, aiming to make financial freedom accessible to everyone.
- **Entity Type**: Private (later-stage, over $1.1B total funding)
- **Headquarters**: Toronto, Ontario, Canada
- **Founded**: 2014 (10 years ago as of 2024, per company narrative)
- **Founders**: Michael Katchen (Co-founder & CEO); other co-founders include Brett Huneycutt (Co-founder & CPO)

## Core Business
- **Primary industry**: Financial technology (fintech) – online brokerage, robo-advising, digital banking, and crypto trading.
- **Target customers**: B2C (individual Canadians, from beginners to experienced investors) and B2B (business chequing, investing, and group plans).
- **Mission**: “To help everyone achieve financial freedom by making simple, smart, and affordable financial products for everyone.” [wealthsimple.com](https://www.wealthsimple.com/en-ca/about)

## Products & Services
- **Trade**: Commission-free trading of stocks, ETFs, options ($0 contract fees), and cryptocurrency. [wealthsimple.com](https://www.wealthsimple.com/en-ca)
- **Invest**: Expertly built automated portfolios for various risk tolerances and goals.
- **Chequing**: A high-interest chequing account with rewards and no fees.
- **Business**: Chequing, investing, and group retirement plans for companies.
- **Advice**: Access to human financial advisors for personalized wealth management.

## Market Standing
- **Valuation/Market Cap**: Not publicly disclosed.
- **Key Metric**: Over $100 billion in assets under administration (as of 2026); more than 4 million clients; 1,500+ employees. [wealthsimple.com](https://www.wealthsimple.com/en-ca)
- **Total Funding**: Over $1.1 billion raised across multiple rounds. [wealthsimple.com](https://www.wealthsimple.com/en-ca/careers)
- **Notable Investors/Partners**: Power Corporation of Canada, Inovia Capital, Meritech Capital, TCV, Greylock Partners, Sagard Holdings, and others (board includes Paul Desmarais III, Patrick Pichette, Amy Bohutinsky, etc.). [wealthsimple.com](https://www.wealthsimple.com/en-ca/about)
- **Growth Signals**: Fastest-growing Canadian online brokerage in 2025 by asset and trading volume growth (Investor Insight / ISS Canada). [wealthsimple.com](https://www.wealthsimple.com/en-ca)

## Competitive Advantages
- **All-in-one platform**: Combines investing, trading, banking, crypto, and advice in a single, simple interface.
- **Canadian-first focus**: Deeply understands the Canadian market (RRSP, TFSA, FHSA, etc.) and regulatory environment.
- **Low-cost model**: Commission-free trades, no account minimums, competitive interest rates.
- **Strong brand trust**: Over 4 million users and a reputation for transparency and customer-centric design.

## Strategic Focus
- **Product expansion**: Continuously adding new features (e.g., options trading, high-interest chequing, business accounts).
- **AI integration**: “Build with AI” is an operating expectation; using AI to improve products and internal efficiency. [wealthsimple.com](https://www.wealthsimple.com/en-ca/culture)
- **Scaling the team**: Actively hiring across engineering, product, design, and business roles to support growth.
- **Deepening client relationships**: Moving from transactional to holistic financial wellness.

## Why Work Here
- **Culture**: “Maker-owner” philosophy – everyone is expected to ship, take ownership, and stay close to the work. Flat hierarchy, autonomy, and high impact.
- **Flexible work**: Hybrid model with a central Toronto HQ and coworking hubs in Calgary, Vancouver, NYC, and San Francisco. Teams gather in person 2–4 times per year for onsites; R&D teams have “Go! Days” every 6 weeks. [wealthsimple.com](https://www.wealthsimple.com/en-ca/careers)
- **Benefits**: 20 vacation days, 90 Days Away program (extended remote work), top-tier health benefits, $5,000/year mental health support, $1,500/year professional development, $1,500/year wellness & home office, equity for full-time employees, paid parental leave, and a 1.75% interest rate on chequing. [wealthsimple.com](https://www.wealthsimple.com/en-ca/careers)
- **Engineering culture**: Emphasis on moving fast, shipping often, and using AI as a core tool. R&D teams have dedicated “Build Days” for deep work.
- **Early talent program**: Internships and co-ops with mentorship from industry leaders.

## Sources
1. [wealthsimple.com](https://www.wealthsimple.com/en-ca) – Company overview, products, client count, growth stats
2. [wealthsimple.com](https://www.wealthsimple.com/en-ca/careers) – Careers page, benefits, work model, funding, employee count
3. [wealthsimple.com](https://www.wealthsimple.com/en-ca/about) – About page, leadership, board, mission, investors
4. [wealthsimple.com](https://www.wealthsimple.com/en-ca/culture) – Culture manual, values, maker-owner philosophy, AI expectations
5. [jobs.ashbyhq.com](https://jobs.ashbyhq.com/wealthsimple) – Current job openings

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