Enablement Program Specialist, Tailscale
Onboarding
$120-150k
+ Equity incentive plan and variable commission (for quota-based roles)
A zero config VPN for building secure networks
Be an early applicant
A zero config VPN for building secure networks
201-500 employees
Be an early applicant
$120-150k
+ Equity incentive plan and variable commission (for quota-based roles)
201-500 employees
Company mission
To remove overhead and complexity from the “long tail” of software and operational problems that people face every day.
Role
Who you are
- 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
- Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!
What the job involves
- 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
- Own and continuously improve onboarding for new revenue hires, from pre-boarding through ramp milestones with the potential to lead in person sessions
- 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)
Our take
The internet is a global phenomenon, but often online activity is unprotected which leaves users vulnerable to hackers on public networks. Additionally certain sites are inaccessible or censored depending on the users location. Use of a VPN enables a secure connection through an encrypted virtual tunnel which also disguises IP addresses. Traditional VPN's tunnel all network traffic through a central gateway server which can affect reliability, and VPN's almost always slow connection speed.
Tailscale is a VPN service built on top of a secure network fabric, which is unlike a traditional VPN provider as it ensures encrypted point-to-point connections by using the open source WireGuard protocol. Tailscale is configured, on average, in a matter of minutes, while other solutions take weeks to fully implement and then require several hours a week of maintenance.
The product has been well received, with reviewers agreeing that it is easy to set up and a great tool for developers. The company plans to develop its product further by tackling the complexity of software and confronting operational problems that people face daily. Off the back of impressive 2025 funding, Tailscale is expanding its engineering, product and sales teams as well as its global reach, all to empower small teams to build systems that scale, without scaling overhead.
Steph
Company Specialist at Welcome to the Jungle
Insights
81% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Apr 2025
$160m
SERIES C
May 2022
$100m
SERIES B
Total funding: $275m
Company benefits
- Flexible (and reasonable) working hours—work/life balance is exceptionally important to us
- Competitive compensation, stock options and 401(k) (for United States-based employees)
- Comprehensive medical/dental/vision benefits, and more
- 4 weeks of paid vacation (standard across the company) + 12 company holidays per year
- An allowance for equipment to help you personalize your workspace
Company HQ
King West Village, Toronto, ON
Leadership
Avery Pennarun
(Co-Founder & CEO)A range of experience in software engineering including Senior Staff Software Engineer at Google Fiber. They co-founded EQL Data in 2009.
David Crawshaw
(Co-Founder & CTO)Previous experience includes working as a Staff Software Engineer at Google before co-founding Tailscale.
David Carney
(Co-Founder)Co-founded Format in 2012, working as a Full Stack Developer, COO and CFO. Also co-founded Form & Method and The Navarra Group.
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