Full-Time

Benefits Lead

Posted on 9/10/2025

Wealthsimple

Wealthsimple

1,001-5,000 employees

Digital wealth platform with automated investing

No salary listed

Toronto, ON, Canada

Remote

Category
People & HR (1)
Requirements
  • 5+ years experience in benefits administration and design
  • Expertise in both Canadian and US benefits plans is required
  • Demonstrated experience acting as a trusted partner to stakeholders, employees, and benefits partners
  • Comfortable making sound decisions under pressure and ambiguity
  • Able to communicate complex ideas in a simple & easy-to-understand way for any audience
  • Excellent interpersonal skills and willingness to work in collaboration with a wide range of stakeholders and teams
  • Thoughtful problem solver, comfortable managing employee escalations and exceptions with sound judgment and discretion
  • Attention to detail and knowledge of what top tier performance looks like
  • Comfortable with thinking outside of the box and being open to new ideas
Responsibilities
  • Design and manage a comprehensive suite of benefits, perks, and other non-monetary rewards programs
  • Own the strategy, design, and administration of Canadian and US core benefits and group retirement plans
  • Serve as the primary point of contact for all employee inquiries and escalations related to benefits
  • Act as the primary benefits partner and main point of contact on benefits-related topics
  • Manage relationships with all benefits and perks providers to ensure high-quality service and seamless administration of employee benefits
  • Spearhead ongoing benefits projects, partnering closely with the Head of Total Rewards
  • Review, audit, and execute on improvements to current benefits programs, policies, and administration processes

Wealthsimple is a digital financial platform that provides tools to help people manage money, invest, trade stocks, buy cryptocurrency, save, spend, and file taxes all in one place. It works by offering services such as automated investing (a robo-advisor that builds and rebalances portfolios), commission-free stock trading, cryptocurrency investments, and quick tax filing. Revenue comes from management fees on investment accounts, transaction fees, and premium service subscriptions. Wealthsimple differentiates itself through a user-friendly, tech-enabled experience that aims to be more human-centric and accessible, especially for young professionals and tech-savvy users, while offering a broad set of financial tools in one platform. Its goal is to simplify financial management and make financial services easy to use for a wide audience.

Company Size

1,001-5,000

Company Stage

Private

Total Funding

$1.4B

Headquarters

Toronto, Canada

Founded

2014

Simplify Jobs

Simplify's Take

What believers are saying

  • Cross-selling across investing, saving, spending, tax, and crypto deepens customer lifetime value.[4][7]
  • Over four million Canadians and $125 billion AUA signal strong product-market fit.[Recent news articles]
  • Stablecoin settlement with Visa Canada strengthens back-end payments infrastructure and liquidity management.[Recent news articles]

What critics are saying

  • Robinhood's Canadian expansion pressures Wealthsimple's commission-free trading and acquisition economics.[Recent news articles]
  • Traditional banks can bundle SME banking products and weaken Wealthsimple's business banking conversion.[Recent news articles]
  • Crypto, IPO Access, and stablecoin operations increase regulatory, operational, and reputation risk.[4][Recent news articles]

What makes Wealthsimple unique

  • Commission-free trading and managed portfolios sit in one Canadian app.[4][8]
  • IPO Access lets retail clients request shares at offering price without minimums.[Recent news articles]
  • Business banking now bundles chequing, credit, and upcoming USD accounts for entrepreneurs.[Recent news articles]

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Your Connections

People at Wealthsimple who can refer or advise you

Benefits

Health Insurance

Life Insurance

401(k) Company Match

401(k) Retirement Plan

Paid Vacation

Unlimited Paid Time Off

Professional Development Budget

Wellness Program

Remote Work Options

Paid Holidays

Growth & Insights and Company News

Headcount

6 month growth

0%

1 year growth

-2%

2 year growth

-2%
Fintech.ca
Feb 18th, 2026
Wealthsimple's $536M raise boosts Canadian fintech as investor appetite for scale grows

Canadian fintech investment activity in 2025 was driven by three major deals: H.I.G. Capital's $898 million buyout of Converge Technology Solutions, Wealthsimple's $536 million equity raise, and Ripple's $200 million acquisition of Rail, according to KPMG Canada. KPMG partner Dubie Cunningham says investors are prioritising mature Canadian fintechs with strong customer penetration and scalable platforms. She expects this trend to continue in 2026, particularly as Canada's open banking framework launches later this year. By sector, AI fintechs received the most funding deals with 29, followed by crypto and blockchain companies with 26. KPMG's Kareem Sadek predicts Canada's new stablecoin regime will drive increased investor interest in digital assets in 2026, reducing regulatory ambiguity and enabling broader adoption of blockchain-based solutions.

Private Capital Journal
Jan 22nd, 2026
Wealthsimple Investments raises $532M across 6 private funds, up 76% from 2024

Wealthsimple Investments Inc., a subsidiary of Wealthsimple Financial Corp., raised $531.62 million across six private investment funds in 2025, up from $301.97 million across two funds in 2024. The Canadian firm introduced two new funds this year: Wealthsimple Private Infrastructure Fund I, raising $3.05 million, and Wealthsimple Private Market Fund I, raising $8.39 million. Its largest fund, Wealthsimple Private Equity Fund I, raised $201.22 million, whilst Wealthsimple Private Credit Fund 1 Trust raised $178.19 million. Wealthsimple Investments is a registered Investment Fund Manager and Investment Dealer. The company also manages Wealthsimple Venture Fund I separately, whilst its ETF funds are managed by Mackenzie Financial Corporation.

PR Newswire
Oct 27th, 2025
Wealthsimple raises $750M at $10B valuation

Wealthsimple announced a CAD $750 million equity round at a CAD $10 billion post-money valuation to boost growth. The round includes a $550 million primary offering and a secondary offering of up to $200 million. It is co-led by Dragoneer Investment Group and GIC, with participation from CPP Investments, Power Corporation of Canada, IGM Financial Inc., ICONIQ, Greylock, and Meritech. This investment underscores strong global confidence in Wealthsimple's future in financial services.

Fintech.ca
Sep 22nd, 2025
Simple Ventures Raises $15M to Build Canadian Companies | Fintech.ca

Canadian venture builder Simple Ventures has raised $15 million to accelerate the creation of new companies at home and entice Canadian founders abroad to return. The round drew backing from TD Innovation Partners (TDIP), Sun Life, Sobeys, and high-profile founder-operators including Mike Katchen (Wealthsimple), Harley Finkelstein (Shopify), and Joanna Griffiths (Knix), alongside other prolific investors […]

BetaKit
Jun 11th, 2025
Wealthsimple Reveals First Credit Card, Expanded Chequing Account At Inaugural Product Showcase

Toronto FinTech firm pitches “an alternative that is better than a bank” at first Wealthsimple Presents

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