Senior Associate, CXO Systems Design & Optimization
Wealthsimple
Design
Toronto, ON, Canada
Posted on Oct 28, 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 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'll have the opportunity to:
- Lead cross-functional projects and driving changes to our tools that impact the entire organization. You'll be the go-to project manager for initiatives that touch multiple teams.
- Craft elegant solutions in our tools that not only work smoothly but also align with our business goals.
- Investigate client and agent issues, diagnosing unexpected behaviors, and coming up with solutions that scale.
- Keep a vigilant eye on the health of our tools by monitoring core KPIs that impact the client experience. You'll proactively dive into the system to identify and address blindspots when anomalies pop up.
- Participate in the development of a comprehensive roadmap for our tools, with a laser focus on eliminating tech debt and building scalable solutions for the future.
- Develop and maintaining comprehensive expertise in our technology stack. You'll be responsible for staying on top of tool updates, ensuring the team remains at the forefront of our systems' capabilities.
- Partner with teams across the organization and external vendors to design AI-powered solutions that automate customer support workflows. You'll optimize both customer experience and operational efficiency through thoughtful implementation.
- Serve as the critical bridge between AI strategy and practical implementation, translating complex technical capabilities into elegant system designs that integrate seamlessly with our existing infrastructure.
- Mentor team members on systems thinking approaches that uncover process complexities and interdependencies. You’ll guide associates in developing architectural solutions that balance immediate efficiency with long-term adaptability.
What you'll bring:
- You excel at communicating complex ideas with ease and succinctness, making you an ideal collaborator with leadership teams.
- You're skilled at asking probing questions, allowing you to design and execute optimal workflows that meet both user needs and system requirements.
- You thrive on tackling problems outside your comfort zone. As a Senior Systems Associate, you're ready for the unexpected, knowing that each day may bring new challenges.
- You have a passion for process improvement and resource development. Your initiatives help your team work more effectively and efficiently.
- You're a resourceful problem-solver. When faced with uncertainty, you know how to find answers.
- You have an eye for detail and take pride in sweating the small stuff. Your meticulous approach ensures high-quality outcomes in all your work.
- You have a team-first mindset, always looking for ways to contribute to your colleagues' success while delivering your best work.
- You're adept at managing your time and resources, effectively prioritizing tasks to meet project deadlines and organizational objectives.
- You have experience with AI technologies and can develop effective prompts, evaluate AI outputs, and optimize AI-powered solutions.
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.
