We encourage you to help us break that statistic!

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 secure, like it used to be. Networks are increasingly made up of machines talking to machines. CI/CD pipelines, Kubernetes workloads, AI agents, and cloud services all need secure connectivity, often across environments and without human intervention. Tailscale provides the building blocks for these connections. Your job is to turn them into a cohesive product experience and a standalone line of business.

Enabling AI agents to securely connect to the tools, services, and private infrastructure they need to operate.

You’ll work closely with engineering, design, and go-to-market teams to make Tailscale the obvious choice for workload connectivity, from a developer's first integration to production deployments at scale.

Define the end-to-end developer experience for connecting workloads, from authentication and deployment through monitoring and troubleshooting.

Define and own success metrics for workload adoption, activation, retention, and revenue, using data to guide product investments.

Build deep customer insight by working directly with developers, platform engineers, and infrastructure teams.

Collaborate across product teams on shared foundations, including identity, access controls, networking, and developer tooling.





Strong technical fluency in cloud-native infrastructure, including Kubernetes, containers, networking, infrastructure automation, and workload identity.

- Experience building products for developers and platform engineers, with a strong appreciation for APIs, documentation, and operational experience.
- Strong commercial judgment, with the ability to turn technical capabilities into differentiated products and sustainable revenue.
- Ability to work directly with sophisticated technical customers and lead cross‑functional teams through ambiguity.

Public technical writing, conference talks, or open‑source contributions.

Tailscale's compensation package includes base salary, equity, and comprehensive benefits. 237,180 - $296,140 CAD

An inclusive, flexible environment where you can be your authentic self. This includes a base salary, an equity incentive plan and variable commission (for quota‑based roles).

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.

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.

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. 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).

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. Will you now or at any point in the future require visa sponsorship to work in the country for which you are applying? We are not currently able to provide immigration support for this role. We are not currently providing relocation support for this role.

📌 Product Manager Remote (m/f/d) (Montreal)
🏢 Tailscale
📍 Montreal