120K–150K USD / year
Enablement Program Specialist, Onboarding
OperationsRemote — unknown
Published on 2026-09-17
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About this role
The Enablement Program Specialist will manage the onboarding and continuous training programs for the revenue team at Tailscale. This role involves collaborating with various departments to ensure new hires ramp up effectively and ongoing development programs deliver measurable results.
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.
- Create scalable enablement paths that support career progression.
- Partner with managers to identify skill gaps.
- Instrument programs with metrics and iterate based on feedback.
- Manage the Tailscale LMS for new-hire materials.
What we're looking for
- 2–4+ years in revenue/sales enablement.
- Ability to design and scale enablement programs.
- Strong project management skills.
- Excellent written communication abilities.
- Strong stakeholder management skills.
- Data-driven mindset.
Nice to have
- Experience using AI tools for learning environments.
- Prior selling experience to technical personas.
Benefits
- Comprehensive group benefits with no waiting period.
- Employer-funded retirement contributions.
- Customizable home office setup.
- Paid parental leave program.
- Support for personal and professional development.