Software Engineer, Product Strategy

Tailscale

15h•$218,420 - $302,840•Remote

About The Position

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.

Requirements

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 experience is a must; 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

Nice To Haves

Python and/or TypeScript
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

Responsibilities

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.

Benefits

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 off-sites, and collaborate in person with teammates across Canada, the United States, and the United Kingdom. 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 $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.

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