Staff Product Operations Manager

The posting, as Tailscale wrote it

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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 seeking an experienced Staff Product Operations Manager to own how Tailscale’s Product org operates. You’ll look across how Product plans, launches, learns from customers, and measures results, identify the gaps that matter most, and design the systems to close them. You’ll partner with Product leadership as a strategic contributor and shape how Product connects to GTM, Support, Data, and company planning.

Because we’re an early-stage, fully remote company, we’re looking for someone who works with full autonomy. You’ll turn broad goals into clear strategies, decide what’s worth pursuing, and build alignment at every level. You’ll report to the Manager, Program Management.

Key Responsibilities

You will work as part of the Program Management team to:

Roadmap health

• Own the strategy and standards for roadmap health, including how initiative and epic dates and health are defined, tracked, and reported.
• Evolve the Product org’s continuous planning cadence as the company grows, and connect it to company planning.
• Own the external roadmap and how it’s communicated to customers and the field.

Product launch health

• Define the launch framework and readiness standards used across Product, PMM, Sales, and Support.
• Partner with PMM, Sales, and Support leaders to make launch readiness consistent and measurable.

Internal documentation and onboarding

• Set the standards for how Product org documentation is structured and maintained, so teams can keep it current themselves.
• Design the Product team’s onboarding program as the org grows.

Feature request health

• Design the end-to-end feature request system, from intake in Jira to its connection with roadmap decisions.
• Give Product leadership a clear view of demand and how it’s reflected in the roadmap.

Customer insight

• Own a single customer insight strategy that combines closed-lost data, feature requests, QBRs, and community feedback from Discord, Reddit, and GitHub into a view that informs prioritization.

Operating rhythms

• Own the Product org’s operating model, including the customer QBR process for EPD and

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• 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 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 $500 USD to customize your workstation to make it your own.
• Paid parental leave program . We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

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 .