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Salary: CAD 168,800 - 201,000 / annual
Tailscale, a fully distributed secure networking platform company founded in 2019, is seeking an Enablement Program Specialist to own onboarding and continuous enablement programs for the revenue team.
You will design, launch, and manage end-to-end enablement initiatives that help new customer-facing hires ramp quickly and keep the sales organization sharp. Your responsibilities span the full employee lifecycle: pre-boarding through ramp milestones, continuous skill development, product launches, process rollouts, and certification programs. You'll build scalable, role-specific enablement paths that support core competencies and career progression.
Key responsibilities include:
- Owning and continuously improving onboarding for new revenue hires from pre-boarding through ramp milestones
- Extending onboarding into continuous everboarding enablement so reps keep building skills after initial ramp
- Designing, launching, and managing recurring enablement programs (skill development, product launches, process rollouts, certifications)
- Building scalable, role-specific enablement paths that support core competencies and career progression
- Managing logistics, content, and cadence of programs end-to-end, keeping them on schedule and on quality
- Partnering with frontline managers and sales leadership to identify skill gaps and deliver targeted programs
- Instrumenting programs with metrics (ramp time, completion, competency) and iterating based on data and rep feedback
- Managing the Tailscale LMS to ensure new-hire materials stay current and accessible
- Exploring and piloting AI-driven learning tools (e.g., an AI tutor for asynchronous onboarding)
You'll work cross-functionally with Sales, Customer Engineering, Support, Customer Success, Marketing, and Product, thriving in a remote-first, high-growth environment.
REQUIREMENTS:
- 2–4+ years in revenue/sales enablement, with hands-on program and onboarding ownership
- Demonstrated ability to design, launch, and scale enablement programs in fast-paced, high-growth environments
- Strong project management skills and meticulous attention to detail
- Excellent written communication and facilitation/instructional-design instincts
- Strong stakeholder management across multiple functions and seniority levels
- Data-driven mindset and comfortable using performance metrics, rep feedback, and tool insights to iterate on programs
- High degree of ownership and someone who thrives in ambiguity and enjoys building from scratch in a remote-first culture
- Bonus: Experience using AI tools to build more efficient and effective learning environments
- Bonus: Prior selling experience, especially to technical personas such as IT, engineering, and security
About Tailscale
AI / Data / Infrastructure; SaaS / Enterprise Software — secure networking platform built on WireGuard.
