Enablement Program Specialist, Onboarding - Tailscale

About 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. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

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.

What We Offer

• An inclusive, flexible environment: Flexibility in how and when you work to empower work-life integration.
• A competitive total compensation package: Base salary, equity incentive plan, and variable commission (for quota-based roles).
• Comprehensive group benefits: Coverage for health, vision, dental, and more with no waiting period.
• Remote-first company: Work fully remotely, leverage corporate co-working memberships (WeWork and similar), and join virtual/in-person social events.
• Employer-funded retirement contributions: Dollar-for-dollar match up to 0.75% of eligible compensation.
• IRL Connections: Annual company retreat, team off-sites, and travel support across Canada, the US, UK, and Singapore.
• Learning and development: $1,500 USD annual professional development budget, plus mentorship, coaching, and internal growth paths.
• Paid time off: Flexible paid time off program.
• Home office setup: Company-owned laptop (Mac or PC), monthly home internet reimbursement, and $500 USD for workstation setup.
• Parental leave: 20 weeks for birthing parents, 16 weeks for non-birthing parents.