AI-Driven Revenue Enablement Lead

WinsAbove; Canada; Hybrid; CAD 169,000 - 201,000; Full time

Benefits offered by this job

Inclusive environment

Competitive compensation

Comprehensive benefits

Remote-first culture

Professional development budget

Job summary

Tailscale is seeking a Revenue Enablement professional to own onboarding programs and drive continuous learning for the revenue organization. You will design, launch, and manage scalable enablement paths, partnering with sales leadership to close skill gaps and accelerate ramp for new hires.

You will build data-driven programs, leverage the LMS, and explore AI-driven tools to make onboarding faster and more impactful in a remote-first environment across Canada and beyond.

Qualifications

• 2-4+ years in revenue/sales enablement or onboarding ownership.
• Ability to design, launch, and scale enablement programs in fast-paced environments.
• Strong project management and meticulous attention to detail.
• Excellent written communication and instructional-design instincts.
• Strong stakeholder management across multiple functions and seniority levels.

Responsibilities

• Own and continuously improve onboarding for new revenue hires from pre-boarding through ramp milestones.
• Extend onboarding into continuous 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 logistics, content, and cadence of programs end to end, ensuring schedule and quality.
• Partner with frontline managers and sales leadership to identify gaps and deliver targeted programs.
• Measure programs with metrics and iterate based on data and rep feedback.
• Manage the LMS to keep materials current and accessible.
• Explore AI-driven learning tools to improve onboarding efficiency.

Skills

Project management

Instructional design

Stakeholder management

Written communication

Data-driven mindset

Tools

Tailscale LMS

Job description

Tailscale is seeking a Revenue Enablement professional to own onboarding programs and drive continuous learning for the revenue organization. You will design, launch, and manage scalable enablement paths, partnering with sales leadership to close skill gaps and accelerate ramp for new hires.

You will build data-driven programs, leverage the LMS, and explore AI-driven tools to make onboarding faster and more impactful in a remote-first environment across Canada and beyond.