United Kingdom · Remote OK
$77k–$96k/yr
About Tailscale 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. From hobbyists to multinational corporations, …
Skills: TCP/IP, DNS, Subnetting, Firewalls, NAT Traversal
United States · Remote OK
$97k–$121k/yr
About Tailscale 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. From hobbyists to multinational corporations, …
Skills: TCP/IP, DNS, Subnetting, Firewalls, NAT Traversal
Canada · Remote OK
$130k–$162k/yr
About Tailscale 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. From hobbyists to multinational corporations, …
Skills: TCP/IP, DNS, Subnetting, Firewalls, NAT Traversal
Vancouver, British Columbia, Canada · Hybrid
$134k–$168k/yr
About Tailscale 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. From hobbyists to multinational corporations, …
Skills: Prospecting, Closing, Pipeline Management, Sales Forecasting, Multi-threading
Denver, Colorado, United States · Hybrid
$120k–$150k/yr
About Tailscale 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. From hobbyists to multinational corporations, …
Skills: Prospecting, Closing, Pipeline Management, Sales Forecasting, Technical Sales
Denver, Colorado, United States · Hybrid
$100k–$125k/yr
About Tailscale 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. From hobbyists to multinational corporations, …
Skills: Prospecting, Closing, Upselling, Renewals, Pipeline Management
Denver, Colorado, United States · Hybrid
About Tailscale 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. From hobbyists to multinational corporations, …
Skills: Closing, Account Management, Upselling, Renewals, Pipeline Management
Canada · Remote OK
$218k–$303k/yr
About Tailscale 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. From hobbyists to multinational corporations, …
Skills: Go, Rapid Prototyping, LLM Integration, Networking, API Integration
United States · Remote OK
$163k–$226k/yr
About Tailscale 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. From hobbyists to multinational corporations, …
Skills: Go, Rapid Prototyping, LLM Integration, Networking, API Integration
United States · Remote OK
$150k–$200k/yr
About Tailscale 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. From hobbyists to multinational corporations, …
Skills: Technical Discovery, Solution Architecture, TCP/IP, DNS, Routing
Canada · Remote OK
$201k–$268k/yr
About Tailscale 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. From hobbyists to multinational corporations, …
Skills: Technical Discovery, Solution Architecture, TCP/IP, DNS, Routing
United States · Remote OK
$146k–$183k/yr
About Tailscale 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. From hobbyists to multinational corporations, …
Skills: Product Design, B2B Design, Infrastructure Design, User Discovery, GUI Design
Canada · Remote OK
$196k–$245k/yr
About Tailscale 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. From hobbyists to multinational corporations, …
Skills: Product Design, User Experience (UX), User Interface (UI), B2B Design, Infrastructure Product Design
United States · Remote OK
$163k–$204k/yr
About Tailscale 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. From hobbyists to multinational corporations, …
Skills: OAuth2, OIDC, SAML, WebAuthn, SCIM
Canada · Remote OK
$218k–$273k/yr
About Tailscale 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. From hobbyists to multinational corporations, …
Skills: OAuth2, OIDC, SSO, SAML, WebAuthn
United States · Remote OK
$181k–$226k/yr
About Tailscale 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. From hobbyists to multinational corporations, …
Skills: React, Frontend Architecture, Browser Security, HTTP Semantics, Authentication Flows
Canada · Remote OK
$243k–$303k/yr
About Tailscale 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. From hobbyists to multinational corporations, …
Skills: React, Frontend Architecture, Browser Security, HTTP Semantics, Authentication Flows
Canada · Remote OK
$218k–$303k/yr
About Tailscale 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. From hobbyists to multinational corporations, …
Skills: Go (Golang), Application-Layer Networking, Distributed Systems, Socket Programming, Routing Tables
United States · Remote OK
$163k–$226k/yr
About Tailscale 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. From hobbyists to multinational corporations, …
Skills: Go (Golang), Networking Internals, Distributed Systems, Socket Programming, Routing Tables
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Serve as the primary escalation point for complex technical tickets, diagnosing issues related to ACLs, subnet routing, and identity providers. Partner cross-functionally with Product and Engineering teams to reduce user friction and mentor Tier 1 support staff.
Requires 4+ years of technical support experience in a SaaS environment with strong networking fundamentals and proficiency across multiple operating systems. Candidates should have experience with SSO integrations, Kubernetes basics, and a passion for technical tinkering.
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. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.
If you’re passionate about solving technical issues and providing high-quality support to a diverse community of users, this is the role for you. We’re seeking a motivated Support Engineer (Tier 2) to join our growing team of support professionals. You will serve as the face of the company for teams and companies using Tailscale, handling a broad range of tickets that will help flex your technical muscles.
As a Tier 2 engineer, you’ll be part of a distributed team focused on delivering excellent support to our customers and proactively solving friction by partnering with our broader CX team and Product/Eng. This role reports directly to the Support Team Lead and will play a key role in our journey.
As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.
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!
Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.
Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.
Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.
Simple, secure networks for teams of any scale. Built on WireGuard.
For teams who want secure, private networks without weeks of setup and configuration, Tailscale makes it easy. Unlike existing corporate VPNs, Tailscale has no upfront cost, minimal latency, and works with their existing services.
Offices: Toronto, Ontario M6K 3S5, CA · Berkeley, CA 94705, US
Simple, secure networks for teams of any scale. Built on WireGuard.
For teams who want secure, private networks without weeks of setup and configuration, Tailscale makes it easy. Unlike existing corporate VPNs, Tailscale has no upfront cost, minimal latency, and works with their existing services.
Offices: Toronto, Ontario M6K 3S5, CA · Berkeley, CA 94705, US
