Tailscale

8 open remote positions

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

Salary Distribution 7 of 8 jobs

PTO Distribution 5 of 8 jobs

Unlimited PTO 5 jobs (63%)

Parental Leave Distribution

Maternity Leave 1 jobs

26w
26w
26w

Paternity Leave 1 jobs

26w
26w
26w

Benefits Overview 8 of 8 jobs

Dental (8) Equity (8) Medical (8) PTO (8) Vision (8) Parental Leave (5) Development (3) Professional development (3) Remote (3) Co-working (2) Internet reimbursement (2) Parental leave (2) Home Office Stipend (1) Home office setup (1) Internet Reimbursement (1) Professional Development (1) Remote work (1)

Open Positions

Singapore Unlimited PTO 26w maternity 26w paternity

  • Act as the pioneering technical voice for Tailscale in APAC, cultivating market presence and defining regional technical execution strategies.
  • Partner closely with AEs to identify, qualify, design, and close new commercial opportunities, managing the regional pipeline to exceed quota outcomes.
  • Lead discovery workshops, deliver tailor-made product demonstrations, and manage technical POCs that resolve technical objections and shorten sales cycles.

$159,925–$222,230/yr

  • Build prototypes and POCs that showcase Tailscale for AI agents and tooling.
  • Work with reference customers to integrate Tailscale, both for internal adoption and for embedding into their products to enable secure customer connectivity.
  • Create reference architectures and share your work through documentation, open source, community engagement, and conference presentations.

$245,579–$270,213/yr
Canada Unlimited PTO

  • Manage and grow a small, senior team by coaching, developing judgment, and hiring people who make the team better.
  • Partner closely with Sales as a credible technical counterpart on complex enterprise opportunities, helping shape deal strategy and execution quality.
  • Stay current on cloud, DevOps, networking, and security trends, and help the team continue sharpening both technical instincts and communication skills.