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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 is easy, sensible, and secure, 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

Please note, you must reside in the country for which you are applying to be considered for this position. We are not currently providing relocation support for this role.

If you intended to apply for employment in another country where we are hiring, please return to our careers page and apply to the correct country’s job post for this role.

Please note, you must legally be able to work in the country for which you are applying to be considered for this position. We are not currently able to provide immig

📌 Release Manager (Winnipeg)
🏢 Tailscale
📍 Winnipeg