Jobs in Regina, Canada

Tailscale is building the new Internet 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.

Join our Product Strategy team (reporting directly to our Chief Strategy Officer) to show developers and organizations why Tailscale should be their go-to connectivity solution, both internally and for customer-facing workloads. You'll build proof-of-concepts, work directly with customers on integrations, and demonstrate how Tailscale's emerging platform can be leveraged to solve real problems.

• Build prototypes and POCs that showcase Tailscale for AI agents/tooling (MCP gateways, LLM proxies, remote servers, etc.)
• Work with customers to integrate Tailscale—both for internal adoption (VPN replacement with identity-aware networking) and for embedding into their products to enable secure customer connectivity
• Create reference architectures and share your work through documentation, community engagement, and presentations
• Rapidly iterate with input from your colleagues and reference customers to incorporate feedback and build solutions that solve emerging, real-world problems.

Ideal candidates will have experience iteratively developing software in startup-like environments. We don’t expect expertise with every aspect listed below. Let us know where you feel you have the most experience and where you would like to continue developing.

• Strong at rapid prototyping, explaining technical concepts, and working directly with customers in an exploratory, fast-paced environment
• Access control: RBAC/ABAC models, session management, MFA, passwordless auth
• Technical skills: Go and/or Python (TypeScript a plus); third-party API integrations; basic networking
• AI/LLM experience: Use LLMs daily for planning and development; comfortable building tools/apps on top of LLMs
• Identity infrastructure: IdP platforms, identity sync/provisioning, and directory services.
• Authentication protocols: OAuth, OIDC, SAML, SCIM
• Experience validating code for production use with security teams
• Thrive working independently in a remote environment

• Familiarity with Tailscale networking solutions
• Experience with agentic AI tools and security considerations
• Background in developer tooling
• Understanding of networking challenges in multi-cloud and hybrid deployments
• Open source community participation

• Opportunity to shape emerging AI connectivity standards and Tailscale's product strategy
• Travel opportunities to represent Tailscale at industry events

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.

$191,620 - $302,840 CAD

Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!

• 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.
• Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team/department off-sites, or use your individual travel budget to meet up with team members in Canada, the US, or the UK.
• 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 $1000 USD to customize your workstation to make it your own.
• Generous parental leave program from your first day. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups for up to 26 weeks.

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.