Engineering Manager, Strategic Projects

This is a fully remote position, open to applicants in Canada.

📋 Description

• Lead a skilled, senior team of seasoned engineers within a rapidly growing startup.

• Propel business results assessed by the adoption of new platform features, successful customer integrations, and impact on Tailscale's strategic roadmap.

• Make significant design choices on prototypes that frequently transition into production-level projects, maintaining the quality standards for the team's public-facing outputs (reference architectures, open source projects, presentations, customer integrations).

• Establish standards for the team's use of AI coding tools: determining which agents and processes to adopt, implementing review and security protocols around agent-generated code, and ensuring the team maintains a swift workflow without compromising production quality.

• Recruit, mentor, and oversee engineers while cultivating a fun, innovative, and inclusive environment, which includes fostering healthy conflict and a culture of honest, constructive feedback.

• Collaborate across core platform engineering, security, and go-to-market teams on projects that span multiple domains and often involve direct co-development with customers.

• Guide planning across various timeframes, balancing rapid prototype cycles with longer-term strategies regarding the convergence of connectivity, identity, and AI infrastructure.

• Some travel required (~10-15%): mainly for team and company onsite meetings, with occasional participation in conferences or customer visits primarily in North America and potential trips to the EU or APAC.

⛳️ Requirements

• Extensive experience in managing and mentoring engineering teams, focusing on performance, career growth, hiring, and fostering a positive culture.

• Proficiency in developing with Go, the primary programming language utilized across Tailscale's technology stack and this team's prototypes.

• Regular daily engagement with coding agents (such as Claude Code, Cursor, or similar) and LLMs within your engineering processes, alongside a clear perspective on their strengths, weaknesses, and the necessary review and security measures to uphold production standards. Capable of coaching team members to adopt similar practices.

• Comfort with exploratory, customer-centric engineering: translating customer discussions into prototypes and reference designs.

• Familiarity with the fast-paced environment of a strategy team in an early-stage startup: adapting to changing priorities based on market signals, maintaining short timelines from prototype to production, and consistently upholding high standards for deliverables.

🏝️ Benefits

• An inclusive and flexible work environment where you can express your authentic self.

• A competitive total compensation package.

• Comprehensive group benefits with no waiting period.

• Remote-first company—most of our teams operate fully remotely.

• Opportunities to connect with fellow Tailscalars in real life.

• Support for your personal and professional growth.

• Paid time off and a healthy work-life balance.

• A customizable home office setup.

• Generous parental leave program available from your first day.