Enterprise Account Executive, Wealthsimple for Business
Wealthsimple
Sales & Business Development
Remote
Posted on Oct 31, 2025
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 3+ million users who trust us with more than $100 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.
About Wealthsimple for Business
Wealthsimple for Business (W4B) is a modern group savings and retirement offering for employers and their employees. With W4B, employers can offer engaging competitive workplace savings plans to attract and retain top talent. Wealthsimple for Business provides a best-in-class experience for employees, including a suite of group capital accumulation plans alongside their other Wealthsimple accounts, while also providing integrations and other time-saving tools to employers for simple administration.
With approximately one thousand plan sponsors on W4B, we are still considered a new player in this long-standing industry. You should be comfortable with ambiguity, a fast-paced environment, and exploring new segments and product offerings.
The Role
Wealthsimple is looking for an experienced Enterprise Account Executive to help grow our Wealthsimple for Business product line (group savings plans). Reporting to the Head of Enterprise Sales, you will be responsible for developing the Enterprise sales segment by building strong relationships with distribution partners and advisors to attract new business and manage a book of existing relationships. This role requires a balance of hunting for new, cold prospects and nurturing a base of existing advisors and consultants.
Applicants should be self-starters, relationship-oriented, experts in the industry, and ready to be hands-on in delivering results.
In this role you'll have the opportunity to:
- Proactively develop and maintain engaging relationships with advisors to drive excitement about the Wealthsimple for Business group retirement offering.
- Partner with advisors to review quote specifications for potential clients, and write and present proposals to advisors or potential clients.
- Generate new business opportunities by actively prospecting and promoting Wealthsimple’s group retirement offerings directly to sponsors.
- Engage prospects at the C-suite, VP, and Director level across all industries and geographies in Canada, at organizations with at least 500 Canadian Employees.
- Build a deep pipeline of potential customers from outbound efforts, events and brand marketing opportunities, and networking.
- Work with industry partners including other technology partners, benefit brokers, and consultants.
- Effectively manage and organize 40+ opportunities in Salesforce at any given time.
- Run a disciplined sales process, building off the team's previous success while looking for opportunities to make it more efficient.
- Work cross-functionally with the core W4B team to provide product, operations, and go-to-market feedback.
- Be creative – we are constantly entering new parts of the market, pitching new solutions, and developing new programs. We are looking for individuals who are excited to try new things and help us scale.
What you'll bring:
- Drive and Determination: You should have a demonstrated track record of persevering in the face of adversity. This is a role that will involve selling a product that is taking a new approach to a traditional industry, which means you will hear the word “no” a lot.
- Proactiveness: We’re a small team - the expectation is that you will take action without being told. You should have a demonstrated history of working independently and driving your own work in the face of ambiguity.
- Results-oriented: You should have experience (and be excited about!) building and managing your own pipeline in the face of uncertainty to ensure you hit your metrics.
- Deal Closing: You should know how to get to, or influence, the executive decision maker, align the sale to a business goal or need, and manage negotiations.
- Communication and Relationship Building: You should be a concise and articulate communicator while also being able to persuade and convince your audience. You must have strong relationship building skills with external customers to present ideas and concepts creatively and succinctly.
- Relevant Experience: At least 5 years experience selling or advising Group Retirement / Workplace Savings in the Canadian market is required, ideally in large mid-market or enterprise segments. An understanding of capital accumulation and defined benefit plans is preferred. Experience in Group Retirement or Group Benefits is a strong asset.
- Location: We are prioritizing candidates in Western Canada (Alberta, British Columbia) or Quebec for this role.
Nice to have, but not required:
- Experience, familiarity, and comfort with Salesforce, Salesloft, Linkedin Sales Navigator and Gong.
- Fluent in French / Bilingual.
Why Wealthsimple?
🤑 Competitive salary with top-tier health benefits and life insurance
📈 Retirement savings matching plan using Wealthsimple for Business
🌴 20 vacation days per year and unlimited sick and mental health days
📚 Up to $1,500 per year towards wellness and professional development budgets respectively
🛫 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)
💖 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 — join us!
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.
