Tailscale
Tailscale Benefits Overview
Compensation + Benefits
Offers 401(K)
Offers life insurance
Offers disability insurance
Offers company equity
Offers dental insurance
Offers health insurance
Offers mental health benefits
Offers Flexible Spending Account (FSA)
Offers vision insurance
Offers Health Savings Account (HSA)
Provides family medical leave
Offers generous parental leave
Work-Life Balance + Wellbeing
Offers company-sponsored outings
Offers an Employee Assistance Program (EAP)
Offers generous PTO
Provides paid sick days
Provides military leave
Provides paid holidays
Provides bereavement leave
Offers unpaid extended leave
Career Growth + Development
Provides customized development tracks
Company Culture
Utilizes a flexible work schedule
Offers a remote work program
Recently posted jobs
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Lead resolution of high-severity post-sales escalations: investigate and reproduce complex networking and software issues, run customer calls, collect logs and evidence, create engineering-ready handoff packages, identify systemic patterns, and improve tooling and runbooks to raise Support's technical capability.
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Partner with Account Executives to drive new commercial business by leading technical discovery, architecture design, demos and POCs. Guide complex deals, build scalable enablement and provide product/market feedback. Blend deep networking and security expertise with sales acumen to support quota attainment.
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Lead the dataplane product vision and roadmap for Tailscale, owning connectivity features (WireGuard, relays, subnet routing, exit nodes, connectors), performance/reliability SLOs, regional relay capacity, operator tooling (console/CLI), and enterprise/regulatory deployments. Partner with engineering, GTM, and customers to drive production traffic commitments and improve connectivity across diverse NATs, OSes, carriers, and networks.
