Software Engineer – Strategic Projects

🕒 August 5

🇺🇸 United States – Remote

💵 $163k - $226k / year

⏰ Full Time

🟡 Mid-level

🟠 Senior

🧑‍💻 Full-stack Engineer

👻 Ghost score 20%

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Logo of Tailscale

Tailscale

51 - 200 employees

Founded 2020

☁️ SaaS

🔐 Security

📡 Telecommunications

💰 $100M Series B on 2022-05

SaaS • Security • Telecommunications

Tailscale is a company that provides a modern VPN solution founded on WireGuard technology, simplifying networking by creating secure, software-defined networks that connect users, services, and devices with ease. By eliminating the complexities of legacy VPNs, Tailscale offers secure remote access, site-to-site networking, and multi-cloud networking, all while ensuring user-friendly, quick deployment without complex configurations. Recognized for enabling zero-trust environments and seamless workflows, Tailscale supports robust security features such as automated user onboarding, encryption, and access control lists (ACLs). This tool is particularly popular for both enterprise and personal use, praised for its integration capabilities and ease of use, making secure networking accessible anywhere, regardless of infrastructure.

📋 Description

• Partner with product-minded engineers from the start, shaping prototypes such as MCP gateways, LLM proxies, sandboxes, and remote servers for production readiness • Co-own the transition from demos to stable production through hardening, error handling, observability, and operational tooling • Own the production bar for prototypes entering Tailscale’s product surface, including security and review practices around agent-generated code • Work with reference customers on Tailscale integrations for internal adoption and product embedding • Identify and resolve edge cases, regressions, flaky behavior, missing tests, and undocumented operational knowledge • Establish and maintain review, testing, and security practices for rapidly shipping agent-generated code • Travel less than 10%, primarily for team and company onsites, with optional conferences or customer visits in North America

🎯 Requirements

• Experience taking software from prototype to production in startup-like environments • Strong ability to harden, stabilize, and maintain production software • Go experience required • Comfort integrating third-party APIs • Basic networking knowledge • Heavy daily use of coding agents such as Claude Code or Cursor and LLMs in engineering workflows • Understanding of where coding agents accelerate work and fail, and how to apply review, testing, and security practices around them • Ability to collaborate with exploratory, product-minded engineers and jointly own production delivery • Comfort with rapidly shifting priorities and short prototype-to-production timelines • Ability to work independently in a remote environment

🏖️ Benefits

• Base salary, equity incentive plan, and variable commission for quota-based roles • Comprehensive health, vision, dental, and other group benefits with no waiting period • Flexible remote-first work environment • Virtual and in-person social events • Corporate co-working program • Employer-funded retirement contributions matching employee contributions dollar-for-dollar, up to 0.75% of eligible compensation annually • Annual company retreat and team off-sites • $1500 USD annually for professional development • Mentorship, coaching, and internal promotion opportunities • Flexible paid time off • Company-owned laptop (Mac or PC) • Monthly home internet reimbursement • $500 USD home office setup allowance • Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents • Accessible and inclusive hiring process with accommodations available

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