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About Tailscale
Tailscale is making safe connection effortless 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.
About the Role
We’re looking for a Release Manager to own how Tailscale ships our product, both internally and to customers. You’ll build and run our release coordination process and create the operational practices that coordinate product and engineering.
You’ll work closely with engineering leads, product managers, TPMs and support. At first you’ll focus on building release management from the ground up: setting the release cadence, defining roles, building tooling, and agreeing on norms with the teams involved in releases. Later, it will grow into creating processes around other parts of how product and engineering collaborate, like operational metrics.
You should understand how software gets shipped, including branching strategies, build pipelines, feature flags, and rollout mechanics. Your technical aptitude will allow you to design release processes that engineers trust and use.
Tailscale moves fast and your processes should help us maintain our speed. When a process works well, it is nearly invisible - it keeps the right people informed, stays out of engineers’ way, and gives the team a plan.
Key Responsibilities
• Design, implement, and continuously improve Tailscale’s release management process: including release cadence, readiness criteria, rollout coordination, and go/no-go decisions
• Build and maintain the tooling, templates, runbooks, and documentation that make release processes repeatable and low-friction
• Partner with engineering leads and product managers to surface risk early and drive resolution before it becomes a crisis
• Define and track operational metrics that reflect the health of our release practices (e.g., release frequency, change failure rate)
• Keep releases on schedule by facilitating cross-team planning rituals that keep engineering and product coordinated
• Identify and drive systemic improvements to how we operate, using data and judgment to prioritize what actually matters
What We Are Looking For
• 5+ years in engineering operations, release management, or a closely related role at a software company
• Direct experience building or significantly improving release management processes
• Technical fluency: you understand software development deeply enough to have credible conversations with engineers about build systems, deployment pipelines, branching strategies, and production operations
• Strong instincts for what process is worth having and what’s just overhead, and optimizing process for trust and adoption
• Comfort with ambiguity and the ability to build structure from scratch
Nice to Have
• Experience with both client and server software release processes
• Experience at a developer tools, infrastructure, or security-focused SaaS company
• Familiarity with DORA metrics and how to use them to drive meaningful improvement
• Experience with feature flag systems, progressive rollouts, or canary deployments as release tools
• Experience scaling operational practices through periods of rapid team or product growth
• Hands-on experience with Tailscale at work or home
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
$242,540—$302,840 CAD
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.
• Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
• 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, the United Kingdom, and Singapore. 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