MENU
  • Remote Jobs
  • Companies
  • Go Premium
  • Job Alerts
  • Post a Job
  • Log in
  • Sign up
Working Nomads logo Working Nomads
  • Remote Jobs
  • Companies
  • Post Jobs
  • Go Premium
  • Get Free Job Alerts
  • Log in

Benefits Lead

Wealthsimple

Full-time
Canada
communication
insurance
operations
strategy
people operations
Apply for this position

Your career is an investment that grows over time!

Wealthsimple is on a mission to help everyone achieve financial freedom by reimagining what it means to manage your money. Using smart technology, we take financial services that are often confusing, opaque and expensive and make them transparent and low-cost for everyone. We’re the largest fintech company in Canada, with over 4 million users who trust us with more than $80 billion in assets.

Our teams ship often and make an impact with groundbreaking ideas. We're looking for talented people who keep it simple and value collaboration and humility as we continue to create inclusive and high-performing teams where people can be inspired to do their best work.

In this role you will have the opportunity to:

  • Design and manage a comprehensive suite of benefits, perks, and other non-monetary rewards programs that support the holistic health, financial security, and wellbeing of our employees

  • Own the strategy, design, and administration of our Canadian and US core benefits and group retirement plans; as well as other company perks such as leaves policies, employee gifting, and wellness spending accounts

  • Serve as the primary point of contact for all employee inquiries and escalations related to benefits, providing timely and human-first support

  • Act as the primary benefits partner and main point of contact on benefits-related topics including eligibility requests, policy clarifications, and stakeholder and enterprise-wide training

  • Manage relationships with all benefits and perks providers to ensure high-quality service and seamless administration of our employee benefits

What You Will Bring:

  • Relevant work experience: You have 5+ years experience in benefits administration and design. Expertise in both Canadian and US benefits plans is required

  • Stakeholder partnership: Demonstrated experience acting as a trusted partner to stakeholders, employees, and benefits partners

  • Decision making: You are comfortable making sound decisions under pressure and ambiguity   

  • Communication and collaboration: You are able to communicate complex ideas in a simple & easy-to-understand way for any audience. You have excellent interpersonal skills and willingness to work in collaboration with a wide range of stakeholders and teams

  • Problem solving: You are a thoughtful problem solver, comfortable managing employee escalations and exceptions with sound judgment and discretion

  • Attention to detail: You sweat the details. You know what top tier performance looks like because you have been a high achiever yourself

  • Creativity: You are comfortable with thinking outside of the box and being open to new ideas. You are curious and take initiative to experiment with new ideas, technologies, and solutions

In the first six months of the role, you will:

  • Quickly master our Total Rewards philosophy and existing benefits policies and programs

  • Establish strong partnerships with the People Operations team, our benefits brokers, and vendors to build trust and deepen relationships

  • Spearhead ongoing benefits projects, partnering closely with the Head of Total Rewards 

  • Review, audit, and execute on improvements to our current benefits programs, policies, and administration processes to improve efficiency and the employee experience

Why Wealthsimple?

πŸ€‘ Competitive salary with top-tier health benefits and life insurance

πŸ“ˆ Retirement savings matching plan using Wealthsimple for Business

🌴 20 vacation days per year and unlimited sick and mental health days

πŸ“š Up to $1,500 per year towards wellness and professional development budgets respectively 

πŸ›« 90 days away program: Employees can work internationally in eligible countries for up to 90 days per calendar year 

🌎 A wide variety of peer and company-led Employee Resource Groups (ie. Rainbow, Women of Wealthsimple, Black @ WS)

πŸ’– Company-wide wellness days off scheduled throughout the year

We’re a remote-first team, with over 1,000 employees coast to coast in North America. Be a part of our Canadian success story and help shape the financial future of millions β€” join us!

Read our Culture Manual and learn more about how we work.

Technology & Innovation at Wealthsimple

We believe the future belongs to those who innovate boldly. At Wealthsimple, every team member is expected to lean into new technologies, including AI, and tooling to rethink how we work, solve problems faster, and create even greater value. We're looking for people who are not just comfortable with change but energized by it. Our commitment is to build a company that evolves at the pace of the world around us, and we want you to help lead that future.

DEI Statement

At Wealthsimple, we are building products for a diverse world and we need a diverse team to do that successfully. We strongly encourage applications from everyone regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status. 

Accessibility Statement

Wealthsimple provides an accessible candidate experience. If you need any accommodations or adjustments throughout the interview process and beyond, please let us know, and we will work with you to provide the necessary support and make reasonable accommodations to facilitate your participation. We are continuously working to improve our accessibility practices and welcome any feedback or suggestions on how we can better accommodate candidates with accessibility needs.

Apply for this position
Bookmark Report

About the job

Full-time
Canada
Posted 2Β hours ago
communication
insurance
operations
strategy
people operations

Apply for this position

Bookmark
Report
Enhancv advertisement

30,000+
REMOTE JOBS

Unlock access to our database and
kickstart your remote career
Join Premium

Benefits Lead

Wealthsimple

Your career is an investment that grows over time!

Wealthsimple is on a mission to help everyone achieve financial freedom by reimagining what it means to manage your money. Using smart technology, we take financial services that are often confusing, opaque and expensive and make them transparent and low-cost for everyone. We’re the largest fintech company in Canada, with over 4 million users who trust us with more than $80 billion in assets.

Our teams ship often and make an impact with groundbreaking ideas. We're looking for talented people who keep it simple and value collaboration and humility as we continue to create inclusive and high-performing teams where people can be inspired to do their best work.

In this role you will have the opportunity to:

  • Design and manage a comprehensive suite of benefits, perks, and other non-monetary rewards programs that support the holistic health, financial security, and wellbeing of our employees

  • Own the strategy, design, and administration of our Canadian and US core benefits and group retirement plans; as well as other company perks such as leaves policies, employee gifting, and wellness spending accounts

  • Serve as the primary point of contact for all employee inquiries and escalations related to benefits, providing timely and human-first support

  • Act as the primary benefits partner and main point of contact on benefits-related topics including eligibility requests, policy clarifications, and stakeholder and enterprise-wide training

  • Manage relationships with all benefits and perks providers to ensure high-quality service and seamless administration of our employee benefits

What You Will Bring:

  • Relevant work experience: You have 5+ years experience in benefits administration and design. Expertise in both Canadian and US benefits plans is required

  • Stakeholder partnership: Demonstrated experience acting as a trusted partner to stakeholders, employees, and benefits partners

  • Decision making: You are comfortable making sound decisions under pressure and ambiguity   

  • Communication and collaboration: You are able to communicate complex ideas in a simple & easy-to-understand way for any audience. You have excellent interpersonal skills and willingness to work in collaboration with a wide range of stakeholders and teams

  • Problem solving: You are a thoughtful problem solver, comfortable managing employee escalations and exceptions with sound judgment and discretion

  • Attention to detail: You sweat the details. You know what top tier performance looks like because you have been a high achiever yourself

  • Creativity: You are comfortable with thinking outside of the box and being open to new ideas. You are curious and take initiative to experiment with new ideas, technologies, and solutions

In the first six months of the role, you will:

  • Quickly master our Total Rewards philosophy and existing benefits policies and programs

  • Establish strong partnerships with the People Operations team, our benefits brokers, and vendors to build trust and deepen relationships

  • Spearhead ongoing benefits projects, partnering closely with the Head of Total Rewards 

  • Review, audit, and execute on improvements to our current benefits programs, policies, and administration processes to improve efficiency and the employee experience

Why Wealthsimple?

πŸ€‘ Competitive salary with top-tier health benefits and life insurance

πŸ“ˆ Retirement savings matching plan using Wealthsimple for Business

🌴 20 vacation days per year and unlimited sick and mental health days

πŸ“š Up to $1,500 per year towards wellness and professional development budgets respectively 

πŸ›« 90 days away program: Employees can work internationally in eligible countries for up to 90 days per calendar year 

🌎 A wide variety of peer and company-led Employee Resource Groups (ie. Rainbow, Women of Wealthsimple, Black @ WS)

πŸ’– Company-wide wellness days off scheduled throughout the year

We’re a remote-first team, with over 1,000 employees coast to coast in North America. Be a part of our Canadian success story and help shape the financial future of millions β€” join us!

Read our Culture Manual and learn more about how we work.

Technology & Innovation at Wealthsimple

We believe the future belongs to those who innovate boldly. At Wealthsimple, every team member is expected to lean into new technologies, including AI, and tooling to rethink how we work, solve problems faster, and create even greater value. We're looking for people who are not just comfortable with change but energized by it. Our commitment is to build a company that evolves at the pace of the world around us, and we want you to help lead that future.

DEI Statement

At Wealthsimple, we are building products for a diverse world and we need a diverse team to do that successfully. We strongly encourage applications from everyone regardless of race, religion, colour, national origin, gender, sexual orientation, age, marital status, or disability status. 

Accessibility Statement

Wealthsimple provides an accessible candidate experience. If you need any accommodations or adjustments throughout the interview process and beyond, please let us know, and we will work with you to provide the necessary support and make reasonable accommodations to facilitate your participation. We are continuously working to improve our accessibility practices and welcome any feedback or suggestions on how we can better accommodate candidates with accessibility needs.

Working Nomads

Post Jobs
Premium Subscription
Sponsorship
Free Job Alerts

Job Skills
API
FAQ
Privacy policy
Terms and conditions
Contact us
About us

Jobs by Category

Remote Administration jobs
Remote Consulting jobs
Remote Customer Success jobs
Remote Development jobs
Remote Design jobs
Remote Education jobs
Remote Finance jobs
Remote Legal jobs
Remote Healthcare jobs
Remote Human Resources jobs
Remote Management jobs
Remote Marketing jobs
Remote Sales jobs
Remote System Administration jobs
Remote Writing jobs

Jobs by Position Type

Remote Full-time jobs
Remote Part-time jobs
Remote Contract jobs

Jobs by Region

Remote jobs Anywhere
Remote jobs North America
Remote jobs Latin America
Remote jobs Europe
Remote jobs Middle East
Remote jobs Africa
Remote jobs APAC

Jobs by Skill

Remote Accounting jobs
Remote Assistant jobs
Remote Copywriting jobs
Remote Cyber Security jobs
Remote Data Analyst jobs
Remote Data Entry jobs
Remote English jobs
Remote Spanish jobs
Remote Project Management jobs
Remote QA jobs
Remote SEO jobs

Jobs by Country

Remote jobs Australia
Remote jobs Argentina
Remote jobs Brazil
Remote jobs Canada
Remote jobs Colombia
Remote jobs France
Remote jobs Germany
Remote jobs Ireland
Remote jobs India
Remote jobs Japan
Remote jobs Mexico
Remote jobs Netherlands
Remote jobs New Zealand
Remote jobs Philippines
Remote jobs Poland
Remote jobs Portugal
Remote jobs Singapore
Remote jobs Spain
Remote jobs UK
Remote jobs USA


Working Nomads curates remote digital jobs from around the web.

© 2025 Working Nomads.