Engineering Manager, Strategic Projects

🕒 May 27

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Tailscale

WebsiteLinkedInAll Job Openings

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

• Manage a talented, senior team of experienced engineers in a growth-stage startup. • Drive business outcomes measured by adoption of new platform primitives, customer integrations landed, and influence on Tailscale's roadmap. • Make major design decisions on prototypes that often graduate into production surface area, and own the quality bar for the team's externally-visible artifacts (reference architectures, open source, talks, customer integrations). • Set the bar for how this team uses AI coding tools: which agents and workflows the team adopts, what review and security practices wrap around agent-generated code, and how the team sustains a fast cadence without lowering the production bar. • Hire, nurture, and oversee engineers while fostering a fun, creative, and inclusive atmosphere, including healthy conflict and a culture of candid, kind feedback. • Collaborate across core platform engineering, security, and go-to-market on projects that span domains and often involve direct customer co-development. • Drive planning across horizons, balancing fast prototype cycles against longer-arc bets on where connectivity, identity, and AI infrastructure are converging. • Light travel required (~10-15%): primarily team and company onsites, with occasional conferences or customer visits concentrated in North America with potential trips to EU or APAC.

🎯 Requirements

• Substantial experience managing and mentoring engineering teams: performance, career development, hiring, and culture • Experience developing in Go, the primary language across Tailscale's stack and this team's prototypes • Heavy daily use of coding agents (Claude Code, Cursor, or similar) and LLMs in your engineering workflow, with a point of view on where they accelerate work, where they fail, and how to wrap them in review and security practices that hold the production bar. Able to coach engineers on your team to operate the same way • Comfort with exploratory, customer-facing engineering: translating customer conversations into prototypes and reference designs • Comfort with the cadence of a strategy team at an early-ish startup: priorities shift with market signal, prototype-to-production timelines are short, and the bar on what ships stays high regardless.

🏖️ Benefits

• An inclusive, flexible environment where you can be your authentic self. • A competitive total compensation package. • Comprehensive group benefits with no waiting period. • Remote first company—most of our teams work fully remotely. • Connect with other Tailscalars IRL. • Support for your personal and professional development. • Paid time off and a healthy work-life integration. • A build-your-own home office setup. • Generous parental leave program from your first day.