Enablement Program Specialist, Onboarding - Tailscale

Tailscale is making safe connection effortless by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more.

About the Role

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).

What We Are Looking For

• 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.

Pay & Benefits

US Base Salary: $120,000 — $150,000 USD + Equity + Benefits

• Inclusive & Flexible Environment: Flexibility in how and when you work to integrate work and life.
• Competitive Compensation: Base salary, equity incentive plan, and variable commission where applicable.
• Comprehensive Group Benefits: Health, vision, dental, and more with no waiting period.
• Remote-First Setup: Work fully remotely with access to corporate co-working spaces (WeWork).
• Employer-Funded Retirement Contributions: Dollar-for-dollar match up to 0.75% of eligible compensation.
• In-Person Connections: Annual company retreat, team off-sites, and travel support for distributed collaboration.
• Learning & Growth: $1,500 USD annual stipend for professional development, plus mentorship and coaching.
• Flexible Paid Time Off: Generous PTO program supporting personal and work-life needs.
• Home Office Workstation: Company-owned laptop (Mac or PC), monthly home internet reimbursement, and $500 USD home office setup budget.
• Paid Parental Leave: 20 weeks for birthing parents, 16 weeks for non-birthing parents.