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 and grow an enterprise sales territory through self-sourced pipeline generation, new customer acquisition, and account expansion. Lead full-cycle sales, strategic account planning, executive and technical stakeholder engagement, complex procurement and security reviews, and cross-functional account teams. Position Tailscale as a secure connectivity and modern networking platform, drive adoption, and build long-term enterprise relationships while consistently exceeding quota.
Software
Partner with Account Executives on enterprise sales cycles by leading technical discovery, architecture, demos, proofs of concept, security reviews, and early adoption. Design secure Tailscale solutions for hybrid, multi-cloud, and on-premises environments, advise networking and security stakeholders, support pipeline and quota outcomes, and provide customer feedback to Product, Engineering, and go-to-market teams. Occasional travel of approximately 10–20% is required.
Software
Develop and maintain Tailscale’s open-source client and backend networking software. Design, test, document, and optimize networking components, distributed systems, and overlay routing features. Own services through observability, incident response, and customer escalations while collaborating with product managers and designers. Apply security-first practices and improve system efficiency, scalability, and stability in a fully remote, asynchronous startup environment.
