Enablement Program Specialist, Onboarding

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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.

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.

CAN Pay Range

$168,800—$201,000 CAD

What We Offer

• An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.

• A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).

• Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!

• Remote first company—most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.

• Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.

• Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.

• Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.

• Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!

• A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.

• Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.

Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.