Tailscale: Software Engineering Manager, Strategic Projects

About Tailscale

Tailscale is building the new Internet, making it easy to securely interconnect people and their devices, regardless of location. Our secure networking solution is used by teams of all sizes, from hobbyists to multinational corporations, to protect networks and share internal tools. Founded in 2019 and fully distributed, we are backed by leading investors including Accel, CRV, and Insight.

Job Description

We are seeking a full-time Software Engineering Manager for our Strategic Projects team. Reporting to the co-founder and Chief Strategy Officer, this team focuses on demonstrating why Tailscale should be the default connectivity substrate for developers and organizations, both for internal infrastructure and for embedding into customer-facing products. A key initiative for this team is Aperture, our identity-aware LLM gateway.

This is an AI-native team that heavily utilizes coding agents as a force multiplier. The ideal manager will be a power user and coach for these tools, ensuring a high bar on code quality, security, and operational rigor while maintaining a fast shipping cadence.

Key Responsibilities

• 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, and influence on Tailscale's roadmap.
• Make major design decisions on prototypes that often graduate into production, owning the quality bar for externally-visible artifacts (reference architectures, open source, talks, customer integrations).
• Set the standard for AI coding tool usage within the team, including agent selection, review and security practices for agent-generated code, and maintaining a fast cadence without compromising quality.
• Hire, nurture, and oversee engineers, fostering a fun, creative, and inclusive atmosphere with healthy conflict and candid feedback.
• Collaborate across core platform engineering, security, and go-to-market teams on cross-domain projects, often involving direct customer co-development.
• Drive planning across multiple horizons, balancing fast prototype cycles with longer-term bets on connectivity, identity, and AI infrastructure convergence.
• Light travel required (~10-15%) for team/company onsites, conferences, or customer visits, primarily in North America, with potential trips to EU or APAC.

What We Are Looking For

• Substantial experience managing and mentoring engineering teams, including performance management, career development, hiring, and culture building.
• Experience developing in Go, the primary language for Tailscale's stack and this team's prototypes.
• Heavy daily use of AI coding agents (e.g., Claude Code, Cursor) and LLMs, with a strong point of view on their acceleration capabilities, limitations, and necessary review/security practices. Ability to coach others on this workflow.
• Comfort with exploratory, customer-facing engineering and translating customer conversations into prototypes and reference designs.
• Comfort with the fast-paced, shifting priorities of a strategy team at an early-stage startup, while maintaining a high bar for production quality.

Nice to Have

• Experience building applications on top of LLMs and agentic systems.
• Networking background (L4-L7 connectivity, browser and DNS behaviors) and familiarity with Tailscale.
• Identity infrastructure background (IdP platforms, identity sync, directory services, protocols like OAuth/OIDC/SAML/SCIM; access control models; session management; MFA; passwordless auth).
• Experience leading teams whose output is publicly visible (open source, devrel, reference implementations) and validating prototype code for production with security teams.

Compensation

Tailscale offers a competitive compensation package including base salary, equity, and comprehensive benefits. The displayed salary range represents the target for a new hire's base salary. Individual offers may vary based on experience and skill set. The CAN Pay Range is $276,040 - $344,380 CAD.

What We Offer

• An inclusive, flexible, remote-first environment.
• Competitive total compensation package (base salary, equity).
• Comprehensive group benefits with no waiting period.
• Virtual and in-person social events, and a corporate co-working program.
• Support for personal and professional development ($1500 USD annually).
• Generous paid time off and a healthy work-life integration.
• Home office setup stipend ($1000 USD) and monthly internet reimbursement.
• Generous parental leave program (up to 26 weeks top-ups).
• Tailscale is committed to an accessible and inclusive hiring process. Accommodations can be requested.