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
Software
Own the vision, strategy, roadmap, and business growth of Tailscale’s Workload Connectivity product. Lead Kubernetes, ephemeral workload, AI agent, and cloud infrastructure connectivity initiatives; define developer experiences, pricing, packaging, success metrics, and integrations. Partner with engineering, design, operations, and go-to-market teams while engaging technical customers and guiding products from strategy through adoption and revenue impact.
Software
Own and grow Tailscale’s analyst relations program by managing analyst inquiries, briefings, evaluations, research participation, and relationships. Synthesize analyst intelligence and market trends into recommendations for Product Marketing, Product, Engineering, and leadership. Develop analyst-facing materials, support market research, track program effectiveness, and strengthen the company’s positioning across cybersecurity, networking, infrastructure, AI, and emerging technology markets.
Software
Own the vision, strategy, and roadmap for Tailscale’s Identity portfolio, including authentication, authorization, SSO, SCIM, access policies, and user management. Lead admin and end-user experiences across the console, API, and clients. Partner with engineering, product, and design, develop customer insights, and translate customer, support, and competitive signals into priorities. Ensure identity services are secure, reliable, intuitive, and integrated across Tailscale’s platform.
