Tailscale benefits

A networking software company that helps people and organizations securely connect devices and services.

19 recorded benefits. Record edited: Mon Aug 31 2026 00:46:43 GMT+0000 (Coordinated Universal Time).

Recorded work model: Remote-first; some roles require in-office collaboration.

Health Insurance

Tailscale's current full-time Remote (US) posting lists comprehensive group coverage for health for employees and their families with no waiting period; plan type, premiums

Eligibility & sources

Sources & dates

  • Jobs board Lead Talent Acquisition Partner, GTM - Tailscale

    Read 2026-08-31T00:42:35.000Z

    Published 2026-08-28T18:28:11.000Z

    Source context

    Current full-time Tailscale posting listed as Remote (United States). Its What We Offer section is standardized benefits evidence for the posted role and does not establish broader US employee eligibility.

Dental Insurance

Tailscale's current full-time Remote (US) posting lists comprehensive group coverage for dental for employees and their families with no waiting period; plan type, premiums

Eligibility & sources

Sources & dates

  • Jobs board Lead Talent Acquisition Partner, GTM - Tailscale

    Read 2026-08-31T00:42:35.000Z

    Published 2026-08-28T18:28:11.000Z

    Source context

    Current full-time Tailscale posting listed as Remote (United States). Its What We Offer section is standardized benefits evidence for the posted role and does not establish broader US employee eligibility.

Vision Insurance

Tailscale's current full-time Remote (US) posting lists comprehensive group coverage for vision for employees and their families with no waiting period; plan type, premiums

Eligibility & sources

Sources & dates

  • Jobs board Lead Talent Acquisition Partner, GTM - Tailscale

    Read 2026-08-31T00:42:35.000Z

    Published 2026-08-28T18:28:11.000Z

    Source context

    Current full-time Tailscale posting listed as Remote (United States). Its What We Offer section is standardized benefits evidence for the posted role and does not establish broader US employee eligibility.

Sick Time

Flexible sick days; it does not separately state US eligibility, accrual, or other policy terms

Eligibility & sources

Sources & dates

  • Benefits page Careers at Tailscale · Tailscale

    Read 2026-08-31T00:42:50.000Z

    Source context

    Current official Tailscale careers page. Its benefits copy is company-level but does not separately state US eligibility for each item; the page identifies Tailscale's team as located in Canada, the United States, and the United Kingdom.

Paid Parental Leave

A paid parental leave program with top-ups of 20 weeks for birthing parents and 16 weeks for non-birthing parents

Pay
Paid
Eligibility & sources

Sources & dates

  • Benefits page Careers at Tailscale · Tailscale

    Read 2026-08-31T00:42:50.000Z

    Source context

    Current official Tailscale careers page. Its benefits copy is company-level but does not separately state US eligibility for each item; the page identifies Tailscale's team as located in Canada, the United States, and the United Kingdom.

  • Jobs board Lead Talent Acquisition Partner, GTM - Tailscale

    Read 2026-08-31T00:42:35.000Z

    Published 2026-08-28T18:28:11.000Z

    Source context

    Current full-time Tailscale posting listed as Remote (United States). Its What We Offer section is standardized benefits evidence for the posted role and does not establish broader US employee eligibility.

Remote Work

Most work as taking place wherever there is Wi-Fi, with some teams visiting an office a few days per week; Tailscale as remote-first, with some roles requiring in-office collaboration

Eligibility & sources

Sources & dates

  • Benefits page Careers at Tailscale · Tailscale

    Read 2026-08-31T00:42:50.000Z

    Source context

    Current official Tailscale careers page. Its benefits copy is company-level but does not separately state US eligibility for each item; the page identifies Tailscale's team as located in Canada, the United States, and the United Kingdom.

  • Jobs board Lead Talent Acquisition Partner, GTM - Tailscale

    Read 2026-08-31T00:42:35.000Z

    Published 2026-08-28T18:28:11.000Z

    Source context

    Current full-time Tailscale posting listed as Remote (United States). Its What We Offer section is standardized benefits evidence for the posted role and does not establish broader US employee eligibility.

Flexible Schedule

Flexible work hours; flexibility in how and when people work, without stating core hours or eligibility terms

Eligibility & sources

Sources & dates

  • Benefits page Careers at Tailscale · Tailscale

    Read 2026-08-31T00:42:50.000Z

    Source context

    Current official Tailscale careers page. Its benefits copy is company-level but does not separately state US eligibility for each item; the page identifies Tailscale's team as located in Canada, the United States, and the United Kingdom.

Co-working Program

Employees can use a corporate co-working program to visit WeWork or similar spaces; amount, locations

Eligibility & sources

Sources & dates

  • Jobs board Lead Talent Acquisition Partner, GTM - Tailscale

    Read 2026-08-31T00:42:35.000Z

    Published 2026-08-28T18:28:11.000Z

    Source context

    Current full-time Tailscale posting listed as Remote (United States). Its What We Offer section is standardized benefits evidence for the posted role and does not establish broader US employee eligibility.

Company-provided Laptop

A company-owned laptop with a Mac or PC choice; other equipment, replacement

Eligibility & sources

Sources & dates

  • Benefits page Careers at Tailscale · Tailscale

    Read 2026-08-31T00:42:50.000Z

    Source context

    Current official Tailscale careers page. Its benefits copy is company-level but does not separately state US eligibility for each item; the page identifies Tailscale's team as located in Canada, the United States, and the United Kingdom.

  • Jobs board Lead Talent Acquisition Partner, GTM - Tailscale

    Read 2026-08-31T00:42:35.000Z

    Published 2026-08-28T18:28:11.000Z

    Source context

    Current full-time Tailscale posting listed as Remote (United States). Its What We Offer section is standardized benefits evidence for the posted role and does not establish broader US employee eligibility.

Workstation Setup Bonus

A $500 USD bonus to customize a workstation

Eligibility & sources

Sources & dates

  • Jobs board Lead Talent Acquisition Partner, GTM - Tailscale

    Read 2026-08-31T00:42:35.000Z

    Published 2026-08-28T18:28:11.000Z

    Source context

    Current full-time Tailscale posting listed as Remote (United States). Its What We Offer section is standardized benefits evidence for the posted role and does not establish broader US employee eligibility.

Internet Reimbursement

A monthly home-internet reimbursement; amount, expense rules

Eligibility & sources

Sources & dates

  • Benefits page Careers at Tailscale · Tailscale

    Read 2026-08-31T00:42:50.000Z

    Source context

    Current official Tailscale careers page. Its benefits copy is company-level but does not separately state US eligibility for each item; the page identifies Tailscale's team as located in Canada, the United States, and the United Kingdom.

  • Jobs board Lead Talent Acquisition Partner, GTM - Tailscale

    Read 2026-08-31T00:42:35.000Z

    Published 2026-08-28T18:28:11.000Z

    Source context

    Current full-time Tailscale posting listed as Remote (United States). Its What We Offer section is standardized benefits evidence for the posted role and does not establish broader US employee eligibility.

Retirement Benefits

Employer-funded retirement contributions; the plan type, employee contribution terms, vesting

Eligibility & sources

Sources & dates

  • Benefits page Careers at Tailscale · Tailscale

    Read 2026-08-31T00:42:50.000Z

    Source context

    Current official Tailscale careers page. Its benefits copy is company-level but does not separately state US eligibility for each item; the page identifies Tailscale's team as located in Canada, the United States, and the United Kingdom.

  • Jobs board Lead Talent Acquisition Partner, GTM - Tailscale

    Read 2026-08-31T00:42:35.000Z

    Published 2026-08-28T18:28:11.000Z

    Source context

    Current full-time Tailscale posting listed as Remote (United States). Its What We Offer section is standardized benefits evidence for the posted role and does not establish broader US employee eligibility.

Retirement Plan Match

It matches retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of eligible compensation; the plan type, vesting

Eligibility & sources

Sources & dates

  • Jobs board Lead Talent Acquisition Partner, GTM - Tailscale

    Read 2026-08-31T00:42:35.000Z

    Published 2026-08-28T18:28:11.000Z

    Source context

    Current full-time Tailscale posting listed as Remote (United States). Its What We Offer section is standardized benefits evidence for the posted role and does not establish broader US employee eligibility.

Employee Equity

An equity incentive plan as part of total compensation; grant size, vesting

Eligibility & sources

Sources & dates

  • Jobs board Lead Talent Acquisition Partner, GTM - Tailscale

    Read 2026-08-31T00:42:35.000Z

    Published 2026-08-28T18:28:11.000Z

    Source context

    Current full-time Tailscale posting listed as Remote (United States). Its What We Offer section is standardized benefits evidence for the posted role and does not establish broader US employee eligibility.

Flexible Time Off

A flexible, paid time-off program; amount, accrual

Eligibility & sources

Sources & dates

  • Jobs board Lead Talent Acquisition Partner, GTM - Tailscale

    Read 2026-08-31T00:42:35.000Z

    Published 2026-08-28T18:28:11.000Z

    Source context

    Current full-time Tailscale posting listed as Remote (United States). Its What We Offer section is standardized benefits evidence for the posted role and does not establish broader US employee eligibility.

Company Holidays

12 paid company holidays; the page does not separately state US eligibility or provide the holiday calendar

Eligibility & sources

Sources & dates

  • Benefits page Careers at Tailscale · Tailscale

    Read 2026-08-31T00:42:50.000Z

    Source context

    Current official Tailscale careers page. Its benefits copy is company-level but does not separately state US eligibility for each item; the page identifies Tailscale's team as located in Canada, the United States, and the United Kingdom.

Holiday Closure

Holiday closures between December 24 and January 1; the page does not separately state US eligibility or the exact closure dates for a particular year

Eligibility & sources

Sources & dates

  • Benefits page Careers at Tailscale · Tailscale

    Read 2026-08-31T00:42:50.000Z

    Source context

    Current official Tailscale careers page. Its benefits copy is company-level but does not separately state US eligibility for each item; the page identifies Tailscale's team as located in Canada, the United States, and the United Kingdom.

Annual Retreat and Offsites

An annual company retreat and team off-sites; frequency beyond the annual retreat, locations

Eligibility & sources

Sources & dates

  • Jobs board Lead Talent Acquisition Partner, GTM - Tailscale

    Read 2026-08-31T00:42:35.000Z

    Published 2026-08-28T18:28:11.000Z

    Source context

    Current full-time Tailscale posting listed as Remote (United States). Its What We Offer section is standardized benefits evidence for the posted role and does not establish broader US employee eligibility.

Professional Development Budget

$1,500 USD annually for professional development

Eligibility & sources

Sources & dates

  • Jobs board Lead Talent Acquisition Partner, GTM - Tailscale

    Read 2026-08-31T00:42:35.000Z

    Published 2026-08-28T18:28:11.000Z

    Source context

    Current full-time Tailscale posting listed as Remote (United States). Its What We Offer section is standardized benefits evidence for the posted role and does not establish broader US employee eligibility.