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.

Job Description

We're seeking a full-time Software Engineering Manager for our Strategic Projects team. Reporting into our co-founder and Chief Strategy Officer, this team exists to show developers and organizations why Tailscale should be their default connectivity substrate, both for internal infrastructure and for embedding into customer-facing products. Aperture, our identity-aware LLM gateway, is one such initiative.

This is an AI-native team. We use coding agents heavily as a force multiplier and expect a manager to be a power user and a coach for others. Our customers demand a high bar on code quality, security, and operational rigour, and we treat that as a reason to use every tool available, including LLMs and coding agents, to ship fast without compromising it.

As Engineering Manager you will mentor a small team of senior engineers; partner with the CSO, PM, and reference customers to turn market signals (particularly around AI infrastructure, agentic tooling, and identity-aware networking) into shippable POCs and reference architectures; provide technical direction on prototypes and integrations, many of which become public artifacts (blog posts, reference repos, conference demos, customer integrations); and help grow the organization through hiring, culture, and process.

Tailscale is fully remote, this team operates with significant ambiguity, and the shipping cadence is fast. Comfort working asynchronously and collaborating with highly technical customers is essential.

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-ish 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

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.

CAN Pay Range

$276,040—$344,380 CAD

*Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications.*We encourage you to help us break that statistic!

What We Offer

• An inclusive, flexible environment where you can be your authentic self. We recognize the impact of diverse voices and backgrounds on the growth of our people, product, and company. And that flexibility in how and when you work empowers our team to integrate work and life.
• 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 company—most 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). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
• 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.

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.

Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.