Senior Program Manager, New Hire Experiences

Build something people love

Wealthsimple's mission is to help everyone achieve financial freedom – by making financial services simple, transparent, and low-cost. We're Canada's largest fintech, trusted by over 3 million clients with more than $100 billion in assets. We move fast, we own our work, and we care deeply about the people using our products. If that sounds like you, keep reading.

We're proud of what we've built — and we're just getting started. Read our Culture Manual and learn more about how we work.

About the role

As Senior Program Manager, you’ll own how new employees experience Wealthsimple. You’ll welcome new hires on day one, set the tone and bring our culture to life - while also giving them early clarity on how we work, what strong performance looks like, and how they can ramp quickly and succeed at Wealthsimple.

This role is focused on experience design, facilitation, and program ownership. You’ll reimagine, elevate, and scale our onboarding experience so it reflects the same bar and craft as our product and brand. You’ll shape and evolve our onboarding program, facilitate key onboarding moments yourself, and work closely with leaders and facilitators across the company to deliver a thoughtful, consistent experience that sets new hires up for success.

This is not an HR operations role. You won’t be responsible for system access, equipment provisioning, or administrative setup. Instead, you’ll partner closely with operational teams so you can stay focused on the human side of onboarding.

In this role, you’ll have the opportunity to:

• Reimagine and build a centralized, AI-enhanced onboarding platform that serves as the single front door for new hires

• Design a cohesive onboarding journey that blends live sessions, asynchronous learning, self-serve content, and early touchpoints into one seamless experience

• Craft a compelling narrative arc across onboarding — bringing our culture, operating norms, and performance expectations to life in a clear, memorable way

• Ensure new hires quickly understand how Wealthsimple works: how decisions get made, what strong performance looks like, and how to ramp effectively

• Facilitate key onboarding moments yourself, setting the tone and modeling the bar for quality and delivery

• Partner with leaders and the People team to create a clear, consistent manager onboarding framework that supports every new hire’s success

• Set quality standards for facilitators and continuously improve the program through feedback, experimentation, and iteration

• Operate with curiosity and extreme ownership — identifying gaps, navigating ambiguity, and raising the bar for the overall onboarding experience

What you’ll bring:

• 5+ years of experience in onboarding, enablement, learning, employee experience, or a related field

• Experience owning and evolving an end-to-end program in a fast-moving environment

• Strong facilitation and executive presence, with comfort presenting to large and senior audiences
  A track record of designing thoughtful, experiential learning moments beyond live sessions

• Fluency with AI tools and a demonstrated ability to use technology to scale impact and improve outcomes

• Comfort operating in ambiguity — you create structure where it doesn’t yet exist

• A systems-thinking mindset — you can zoom out to design cohesive journeys while sweating the details that make experiences feel thoughtful and high quality

• Strong written and verbal communication skills

• The ability to influence senior leaders and work cross-functionally without formal authority

• A warm, credible presence — people trust you quickly

Why this role matters:

Onboarding is one of the most formative moments in an employee’s journey — and one of the highest leverage opportunities we have to shape performance and culture at scale. In this role, you’ll help define what it means to start at Wealthsimple. The experience you design will set the standard for clarity, ambition, and craft from day one — ensuring our onboarding reflects the same bar we hold in our product and brand.

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.

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.