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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.
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 ResponsibilitiesYou 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 the internal MBR, and evolve them as needs change.
Data health
- Define the Product org’s metrics and data strategy, partnering with Data so dashboards scale with new products and features.
Across all areas
- Independently identify gaps in how Product operates, make the case to leadership, and drive solutions.
- Partner with Product leadership on priorities and trade-offs, bringing recommendations rather than status.
Role Success
This role is successful when Product leadership relies on product operations as a strategic partner, customer insight visibly shapes the roadmap, and the Product org’s operating model scales as Tailscale adds products and teams.
What We Are Looking For- 8+ years of experience in product operations, program management, or business operations, including designing an org’s operating model.
- A track record of starting high-impact operations initiatives yourself.
- Experience building customer insight systems that influence product prioritization.
- Experience setting launch frameworks and readiness standards across Product and GTM.
- Experience defining product metrics and data strategy with data teams.
- Systems thinking: the ability to see how Product’s processes affect GTM, Support, and company planning.
- Demonstrated ability to influence senior leaders and build alignment across orgs.
- Experience mentoring others and raising the quality of a team’s work.
- Exceptional written and verbal communication in an asynchronous, remote-first environment.
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.
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 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.
Tailscale Toronto, Ontario, CAN Office
Toronto, ON, Canada
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