Remote Revenue Enablement & Onboarding Specialist

WinsAbove; Northern (KY); Hybrid; USD 120,000 - 150,000; Full time

Benefits offered by this job

Remote first culture

Equity incentive plan

Retirement matching

Company retreats and team off‑sites

$1500 USD for professional development

Home office setup allowance ($500)

Job summary

Tailscale is seeking a Revenue Enablement professional to own onboarding and ongoing enablement programs that accelerate the ramp of new customer‑facing hires. You’ll partner with sales leadership and cross‑functional teams to design, launch, and sustain scalable, role‑specific enablement paths.

You’ll measure success with ramp time, completion rates, and competency gains, while leveraging AI tools to improve learning and adapt to a remote‑first environment with strong career development

Qualifications

• 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 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 to iterate.
• High ownership and ability to thrive in ambiguity in a remote‑first culture.

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 supporting core competencies and career progression.
• Manage logistics, content, and cadence of programs end to end, keeping them on schedule and on quality.
• Partner with 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.
• Manage the Tailscale LMS to keep materials current.
• Pilot AI‑driven learning tools to enhance onboarding.

Skills

Project management

Written communication

Stakeholder management

Data-driven mindset

Ownership in ambiguity

AI tools experience

Sales enablement

Job description

Tailscale is seeking a Revenue Enablement professional to own onboarding and ongoing enablement programs that accelerate the ramp of new customer‑facing hires. You’ll partner with sales leadership and cross‑functional teams to design, launch, and sustain scalable, role‑specific enablement paths.

You’ll measure success with ramp time, completion rates, and competency gains, while leveraging AI tools to improve learning and adapt to a remote‑first environment with strong career development