Engineering Manager, Strategic Projects

Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices, no matter where they are. They serve a diverse range of users from hobbyists to multinational corporations, focusing on creating a future for the Internet that's easy, sensible, and safe.

Location: Canada

Salary: $276,040—$344,380 CAD

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.

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 including base salary, an equity incentive plan, and variable commission (for quota-based roles).
• Comprehensive group benefits with no waiting period, including health, vision, dental, and more for you and your family.
• Remote first company—most of our teams work fully remotely, with some roles requiring in-office collaboration depending on team needs.
• Opportunities to connect with other Tailscalars IRL through retreats, team off-sites, and in-person collaboration.
• Support for personal and professional development with $1500 USD annually for growth.
• Paid time off and a healthy work-life balance.
• Build-your-own home office setup with company equipment and stipends.
• Generous parental leave program from your first day, with top-ups for up to 26 weeks.