Enablement Program Specialist, Onboarding

TailscaleRevenue Enablement

Location: Remote (Canada)Full-TimeMiddle

Salary168,800 - 201,000 CAD per year

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Job Details

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.
High degree of ownership and ability to thrive in ambiguity.
Experience building enablement programs from scratch in a remote-first culture.
Bonus: Experience using AI tools for learning environments.
Bonus: Prior selling experience, especially to technical personas such as IT, engineering, and security.

Own and continuously improve onboarding for new revenue hires, from pre-boarding through ramp milestones.
Extend onboarding into continuous everboarding enablement so reps keep building skills after initial ramp.
Design, launch, and manage recurring enablement programs (skill development, product launches, process rollouts, certifications).
Build scalable, role-specific enablement paths that support core competencies and career progression.
Manage the logistics, content, and cadence of programs end to end, keeping them on schedule and on quality.
Partner with frontline managers and sales leadership to identify skill gaps and deliver targeted programs.
Instrument programs with metrics (ramp time, completion, competency) and iterate based on data and rep feedback.
Manage the Tailscale LMS to ensure new-hire materials stay current and accessible.
Explore and pilot AI-driven learning tools.

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