Software Engineer, Product Strategy

November 19

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Tailscale

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SaaS • Security • Telecommunications

Tailscale is a company that provides a modern VPN solution founded on WireGuard technology, simplifying networking by creating secure, software-defined networks that connect users, services, and devices with ease. By eliminating the complexities of legacy VPNs, Tailscale offers secure remote access, site-to-site networking, and multi-cloud networking, all while ensuring user-friendly, quick deployment without complex configurations. Recognized for enabling zero-trust environments and seamless workflows, Tailscale supports robust security features such as automated user onboarding, encryption, and access control lists (ACLs). This tool is particularly popular for both enterprise and personal use, praised for its integration capabilities and ease of use, making secure networking accessible anywhere, regardless of infrastructure.

51 - 200 employees

Founded 2020

☁️ SaaS

🔐 Security

📡 Telecommunications

💰 $100M Series B on 2022-05

📋 Description

• 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.

🎯 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 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

🏖️ Benefits

• An inclusive, flexible environment where you can be your authentic self. • 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.