[Hiring] Enablement Program Specialist @Tailscale

Role Description

Join our growing Revenue Enablement team, where you'll own onboarding and the enablement programs that keep our revenue team sharp. You'll make sure every new customer-facing hire ramps quickly and that ongoing programs deliver real results. From pre-boarding through ramp and into continuous enablement, you'll design, launch, and run the programs reps rely on by partnering closely with frontline managers and sales leadership, and collaborating across Sales, Customer Engineering, Support, Customer Success, Marketing, and Product.

Key Responsibilities

• 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 (e.g., an AI tutor for asynchronous onboarding).

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, 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.

Requirements

• As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels.
• Tailscale's compensation package includes base salary, equity, and comprehensive benefits.
• The salary range displayed on each job posting represents the target range for a new hire's base salary.
• Individual offers may vary based on experience and skill set.
• US Pay Range: $120,000 — $150,000 USD

Benefits

• An inclusive, flexible environment where you can be your authentic self.
• A competitive total compensation package, including base salary, an equity incentive plan, and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period, covering health, vision, dental, and more for you and your family.
• Remote first company—most of our teams work fully remotely.
• Employer-funded retirement contributions, matching dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
• Connect with other Tailscalars IRL through annual company retreats and team off-sites.
• Support for your personal and professional development with $1500 USD annually for professional development.
• Flexible, paid time off program to support you for any situation life throws your way.
• A build-your-own home office setup with a company-owned laptop and $500 USD to customize your workstation.
• Paid parental leave program with top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).