Enablement Program Specialist – Onboarding

Job not on LinkedIn

🔥 14 minutes ago

🌐 Canada, United States – Remote

🇨🇦 Canada – Remote 🇺🇸 United States – Remote

💵 $168.8k - $201k / year

⏰ Full Time

🟢 Junior

🟡 Mid-level

🚀 Onboarding Specialist

🚫👨‍🎓 No degree required

👻 Ghost score 20%

What it means: how likely this posting is sitting open without active hiring.How to read it: 60% or higher means we think this is a ghost. Lower scores are less of a worry.How we score it: age, reposts, open roles vs team size, how fast jobs close, and whether pay is listed.Fine print: an estimate from public data, not a judgment of the company. Real jobs can score high, so treat it as a hint, not a fact.

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Tailscale

WebsiteLinkedInAll Job Openings

51 - 200 employees

Founded 2020

☁️ SaaS

🔐 Security

📡 Telecommunications

💰 $100M Series B on 2022-05

SaaS • Security • Telecommunications

Tailscale is a company that provides a modern VPN solution founded on WireGuard technology, simplifying networking by creating secure, software-defined networks that connect users, services, and devices with ease. By eliminating the complexities of legacy VPNs, Tailscale offers secure remote access, site-to-site networking, and multi-cloud networking, all while ensuring user-friendly, quick deployment without complex configurations. Recognized for enabling zero-trust environments and seamless workflows, Tailscale supports robust security features such as automated user onboarding, encryption, and access control lists (ACLs). This tool is particularly popular for both enterprise and personal use, praised for its integration capabilities and ease of use, making secure networking accessible anywhere, regardless of infrastructure.

📋 Description

• 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 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, cadence, schedule, and quality end to end • 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 rep feedback • Manage the Tailscale LMS and 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

🎯 Requirements

• 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 • Experience using AI tools to build more efficient and effective learning environments is a bonus • Prior selling experience, especially to technical personas such as IT, engineering, and security, is a bonus

🏖️ Benefits

• 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, and dental coverage 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 0.75% of eligible compensation annually • Annual company retreat and team off-sites • $1500 USD annually for professional development • Mentorship, coaching, and internal promotion opportunities • Flexible paid time off • Company-owned laptop (Mac or PC) • Monthly home internet reimbursement • $500 USD home office workstation customization allowance • Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents