169K–201K CAD / year
Enablement Program Specialist, Onboarding
SalesRemote — unknown
Published on 2026-09-17
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About this role
The Enablement Program Specialist will design and manage onboarding and ongoing enablement programs for the revenue team at Tailscale. They will work closely with various teams to ensure that new hires ramp quickly and continue to develop their skills. The role involves program management, stakeholder collaboration, and data analysis to improve programs.
About the company
Tailscale builds a zero-config mesh VPN on WireGuard so teams can securely connect devices, servers, and cloud resources without traditional VPN complexity.
What you'll do
- Own and improve onboarding for new revenue hires.
- Design and manage continuous enablement programs.
- Manage logistics and content for programs.
- Partner with sales leadership to identify skill gaps and deliver targeted programs.
- Instrument programs with metrics and iterate based on feedback.
What we're looking for
- 2–4+ years in revenue/sales enablement with onboarding ownership.
- Experience designing and launching enablement programs.
- Strong project management skills.
- Excellent written communication skills.
- Data-driven mindset and comfortable using performance metrics.
Nice to have
- Experience using AI tools for learning environments.
- Prior selling experience to technical personas.
Benefits
- Flexible work environment.
- Comprehensive group benefits with no waiting period.
- Employer-funded retirement contributions.
- Supports personal and professional development.
- Paid time off and a healthy work-life integration.