Senior Program Manager, New Hire Experiences

Wealthsimple Technologies

1d • Hybrid

About The Position

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.

Requirements

• 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

Responsibilities

• 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

Benefits

• 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

What This Job Offers

• Job Type: Full-time
• Career Level: Mid Level
• Education Level: No Education Listed