Note: The job is a remote job and is open to candidates in USA. Tailscale is building the new Internet by delivering software that makes it easy to securely interconnect people and their devices. The Engineering Manager for the Strategic Projects team will mentor senior engineers, provide technical direction, and drive business outcomes while collaborating across multiple domains.
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
Skills
- 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
- 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
Benefits
- An inclusive, flexible environment where you can be your authentic self.
- A competitive total compensation package. This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).
- Comprehensive group benefits with no waiting period. Take advantage of coverage for health, vision, dental, and more for you and your family!
- Remote first company97most of our teams work fully remotely. Enjoy a change of scenery wherever you can get wifi, participate in virtual and in-person social events, and leverage our corporate co-working program to visit WeWork (or other similar spaces near you).
- Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom. We support intentional in-person connection through team travel and distributed collaboration.
- Support for your personal and professional development. Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.
- Paid time off and a healthy work-life integration. Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world!
- A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $1000 USD to customize your workstation to make it your own.
- Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks.
Company Overview
Tailscale is a software company that provides zero-configuration virtual private networks (VPNs) for secure connectivity. It was founded in 2019, and is headquartered in Toronto, Ontario, CAN, with a workforce of 201-500 employees. Its website is https://www.tailscale.com.Company H1B Sponsorship
Tailscale has a track record of offering H1B sponsorships, with 2 in 2023. Please note that this does not guarantee sponsorship for this specific role.