by Rat Race Rebellion October 5, 2026
About Tailscale
Tailscale, founded in 2019, is a company dedicated to simplifying secure connections between people and their devices, regardless of their location. Backed by prominent investors like Accel and CRV, Tailscale is at the forefront of building a more accessible and secure Internet for users ranging from small hobbyists to large multinational corporations.
As a full-time, remote-first company, Tailscale offers a flexible work environment that empowers employees to balance work and life effectively. The company supports remote work and encourages employees to work from anywhere with a reliable internet connection.
What Your Day Will Look Like
As an Enablement Program Specialist, your day will involve designing and managing onboarding programs for new hires, collaborating with various departments to enhance skill development, and utilizing AI-driven tools to optimize learning. This role is entirely non-phone based, focusing on program management and development.
Responsibilities & Expectations
- Improve Onboarding: Enhance new hire processes
- Extend Enablement: Develop continuous learning programs
- Design Programs: Launch skill development initiatives
- Manage Logistics: Oversee program schedules and quality
- Partner with Leaders: Address skill gaps with targeted programs
Relevant Experience & Skills Required
- Education Requirements: No degree required
- Program Management: Design and launch initiatives
- Project Management: Strong organizational skills
- Communication Skills: Excellent written communication
- Data-Driven: Use metrics for program iteration
Compensation & Benefits
The compensation for this role is $120,000 – $150,000/yr..
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Before You Apply: Resume Tips for this ATS
Because you are applying directly through the employer’s Applicant Tracking System, your resume needs to be optimized for their software:
- Make sure the words “Enablement Program,” “Onboarding,” and “Revenue Team” appear in your past experience if applicable.
- Highlight any specific experience you have with AI-driven learning tools.
- Ensure your resume clearly states that you are looking for Full-Time work, so the recruiter knows you are aligned with the role.