or apply directly on Tailscale's site. We never take the application ourselves.
Is this posting real?
- This role has been open
- 28 days Tailscale's roles stay open a median of 41 days
- Reposted
- No
- Salary listed
- No 2% of Tailscale's roles list one
- Ghost-job risk at Tailscale
- high 25 stale, 2 reposted of 60 open
- Hiring momentum
- 113 roles opened in the last 90 days ↑ up vs. the prior 90 days
- Last confirmed on the employer's board
- 2026-09-17
Measured from postings appearing on and disappearing from Tailscale's own greenhouse board since 2026-08-03. Full hiring picture for Tailscale.
About this role
As a Customer Support Engineer (Tier 1) at Tailscale, you will be responsible for resolving technical issues and providing support to users, handling a variety of tickets related to configuration and networking challenges. You will work closely with the Customer Experience team and other departments to improve user experience while maintaining high customer satisfaction scores. This role requires a proactive approach to learning and troubleshooting across different operating systems.
- benefits
- 4/5
- freshness
- 4/5
- career value
- 3/5
- role clarity
- 4/5
- pay transparency
- 0/5
Scored from the posting itself — how clearly the role is described, how much it says about pay and benefits, and how recently it was listed. Not a judgement of Tailscale as an employer.
What you need
- Passion for solving technical issues and providing high-quality support
- Foundational understanding of networking fundamentals, including DNS, IP addressing, firewalls, and routing
- Proficiency in troubleshooting across multiple operating systems such as macOS, Windows, Linux, and mobile OS’s
- Familiarity with Jira and Slack for managing workflows and communication
- Excellent written communication skills to explain complex technical concepts with empathy and clarity
- Proactive approach to learning new technologies
What you get
- Comprehensive group benefits with no waiting period for health, vision, dental, and more
- Employer-funded retirement contributions matched dollar-for-dollar up to 0.75% of eligible compensation
- Annual professional development budget of $1500 USD
- Flexible paid time off program
- Build-your-own home office setup with a $500 USD allowance
- Paid parental leave program with top-ups for birthing and non-birthing parents
Worth weighing
- No specific mention of the technologies or tools used in the support process
- High volume of daily tickets may lead to a fast-paced work environment
- Role primarily focuses on Tier 1 support, which may limit exposure to more complex technical challenges
Summarised from Tailscale's posting. Read the full original.
Listed by Tailscale on their greenhouse job board, last confirmed open on 2026-09-17. PitchMeAI is not the employer.
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