About the role

Enablement specialist owning onboarding and continuous learning programs for Tailscale’s secure networking software teams. Measuring ramp and competency outcomes while partnering across revenue functions.

Responsibilities

Own and continuously improve onboarding for new revenue hires, from pre-boarding through ramp milestones
Extend onboarding into continuous everboarding enablement so representatives keep building skills after initial ramp
Design, launch, and manage recurring enablement programs covering skill development, product launches, process rollouts, and certifications
Build scalable, role-specific enablement paths supporting core competencies and career progression
Manage program logistics, content, and cadence end to end while maintaining schedule and quality
Partner with frontline managers and sales leadership to identify skill gaps and deliver targeted programs
Instrument programs with ramp-time, completion, and competency metrics and iterate based on data and representative feedback
Manage the Tailscale LMS to keep new-hire materials current and accessible
Explore and pilot AI-driven learning tools, such as an AI tutor for asynchronous onboarding
Collaborate across Sales, Customer Engineering, Support, Customer Success, Marketing, and Product

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 comfort using performance metrics, rep feedback, and tool insights to iterate on programs
High degree of ownership and ability to thrive in ambiguity and build 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

An inclusive, flexible environment where you can be your authentic self
Competitive total compensation package including base salary, equity incentive plan, and variable commission for quota-based roles
Comprehensive group benefits with no waiting period, including health, vision, dental, and more for you and your family
Remote-first work environment
Virtual and in-person social events
Corporate co-working program
Employer-funded retirement contributions matching employee contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of eligible compensation
Annual company retreat and team off-sites
$1,500 USD annually for professional development
Mentorship, coaching, and internal promotion opportunities
Flexible paid time off program
Company-owned laptop (Mac or PC)
Monthly home internet reimbursement
$500 USD home office setup allowance
Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents
Accessible and inclusive hiring process with accommodations available