Product Strategy Engineer

About Tailscale

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.

Job Description

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.

Key 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.

What We Are Looking For

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 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 Have

• 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

Why You'll Enjoy Working With Us

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

Additional Information

Please note: While this is a remote role, you may be asked to interview in-person at any stage of the interview process.

What We Offer

• An inclusive, flexible environment where you can be your authentic self.
• A competitive total compensation package including base salary, equity incentive plan, and variable commission.
• Comprehensive group benefits with no waiting period including health, vision, dental, and more.
• Remote first company with virtual and in-person social events and corporate co-working program.
• Opportunities for in-person connection through company retreats, team off-sites, and collaboration.
• Support for personal and professional development with $1500 USD annually for professional development, mentorship, coaching, and internal promotion opportunities.
• Flexible, paid time off program.
• Build-your-own home office setup with company-owned laptop, monthly internet reimbursement, and $1000 USD customization allowance.
• Generous parental leave program from your first day.

Scam Awareness

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 .