Shape the future of how people join and grow at a fast-moving organization. As Senior Program Manager, you’ll lead the transformation of our onboarding experience—designing a unified, intelligent journey that reflects the quality of our product and brand. This role is centered on experience design, storytelling, and program leadership, not HR administration.
What You’ll Do
- Design and launch a centralized, AI-powered onboarding platform that acts as the primary entry point for all new employees
- Build an integrated journey combining live interactions, self-paced learning, and early engagement points for a seamless experience
- Develop a clear narrative that brings our culture, decision-making practices, and performance standards to life
- Ensure new hires quickly grasp how the organization works, what excellence looks like, and how to become productive faster
- Lead key onboarding sessions personally, setting a high standard for delivery and engagement
- Collaborate with leaders and People partners to establish a consistent framework for manager support
- Define facilitation standards and refine the program through feedback, testing, and iteration
- Take full ownership of the experience—spotting gaps, solving problems proactively, and driving continuous improvement
Who You Are
- You have 5+ years in onboarding, learning design, employee experience, or a related field
- You’ve led end-to-end programs in fast-paced environments, adapting them over time
- You’re a confident facilitator with strong presence and the ability to engage senior audiences
- You design learning experiences that go beyond sessions—crafting moments that stick
- You’re experienced with AI tools and know how to use technology to scale impact
- You thrive in ambiguity, creating structure where none exists
- You think in systems—balancing big-picture design with attention to detail
- You communicate clearly and persuasively, both in writing and conversation
- You influence without authority and earn trust quickly through warmth and credibility
Work Environment
This is a hybrid role with team locations across North America. You can work from anywhere outside Canada for up to 90 days per year. Our culture values speed, ownership, collaboration, inclusion, and thoughtful building. We move fast, care deeply about our users, and stay open to evolving how we work.
Benefits
- Comprehensive health and life insurance
- Employer-matched long-term savings through a group plan
- 20 vacation days, 4 wellness days, and unlimited sick and mental health days
- 90-day remote work option outside Canada
- Employee resource groups including Rainbow (2SLGBTQ), Women of WS, and Black at WS
Our Commitment to Inclusion
We believe diverse perspectives lead to better products and a stronger team. We encourage applications from all backgrounds, regardless of race, religion, gender, sexual orientation, age, or ability. If you need accommodations during the hiring process, let us know—we’re committed to making it accessible. We may use AI tools to support application review, but all final decisions are made by people.
