Engineering Manager, Strategic Projects

About Tailscale

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. From hobbyists to multinational corporations, teams of every size use Tailscale each day to protect their networks, share access to internal tools, and more. We're building a future for the Internet that's easy, sensible, and safe, like it used to be. Founded in 2019 and fully distributed, we're backed by Accel, CRV, Insight, Heavybit, and Uncork Capital.

The Role

Tailscale is looking for a full-time Software Engineering Manager for its Strategic Projects team. Reporting to the co-founder and Chief Strategy Officer, this team's mission is to demonstrate why Tailscale should be the default connectivity substrate for developers and organizations, both for internal infrastructure and for embedding into customer-facing products. Aperture, an identity-aware LLM gateway, is a key initiative for this team.

This is an AI-native team that heavily utilizes coding agents as a force multiplier. The manager is expected to be a power user and coach for these tools. The team prioritizes code quality, security, and operational rigor, leveraging all available tools, including LLMs and coding agents, to ship rapidly without compromising standards.

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 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.

What We Are Looking For

• 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-stage startup: priorities shift with market signal, prototype-to-production timelines are short, and the bar on what ships stays high regardless.

Nice to Have

• Building applications on top of LLMs and agentic systems (not just using them as dev tools).
• Networking background (L4-L7 connectivity, browser and DNS behaviors), and familiarity with Tailscale itself.
• Identity infrastructure background: IdP platforms, identity sync/provisioning, directory services, and protocols (OAuth, OIDC, SAML, SCIM); access control models (RBAC/ABAC), session management, MFA, passwordless auth.
• Leading teams whose output is publicly visible (open source, devrel, reference implementations) and validating prototype code for production alongside security teams.

Compensation & Benefits

Tailscale offers a competitive compensation package including base salary, equity, and comprehensive benefits. The US pay range for this role is $206,000 - $257,000 USD. Individual offers may vary based on experience and skill set.

What We Offer:

• 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.
• Opportunities for in-person connection through company retreats and team off-sites.
• Support for personal and professional development ($1500 USD annually).
• Generous paid time off and a healthy work-life integration.
• A build-your-own home office setup.
• Generous parental leave program.

Tailscale is committed to providing an accessible and inclusive hiring process. Please contact your recruiter if you require accommodation. Note that our hiring process uses AI-assisted tools, but all hiring decisions are made by people. Be aware of communications originating from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses.