About the role

Engineering Manager for Tailscale's Strategic Projects team, overseeing engineering initiatives. Leading a remote AI-native team to enhance connectivity solutions with high standards of quality.

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 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.

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.