[Remote] Software Engineer, Product Strategy at Tailscale

Canada

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Not SpecifiedCompensation

Mid-level (3 to 4 years)Experience Level

Full TimeJob Type

UnknownVisa

Technology, Networking, CybersecurityIndustries

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
Experience iteratively developing software in startup-like environments

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

Skills

Key technologies and capabilities for this role

rapid prototypingsoftware developmentcustomer integrationreference architecturesdocumentationpresentationsAI agentsLLM proxiesVPNidentity-aware networking

Questions & Answers

Common questions about this position

Is this a remote position?

Yes, the role is fully remote, and ideal candidates thrive working independently in a remote environment.

What technical skills are required for this role?

Required skills include Go and/or Python (TypeScript a plus), third-party API integrations, basic networking, access control like RBAC/ABAC, authentication protocols such as OAuth/OIDC/SAML/SCIM, and AI/LLM experience for building tools/apps.

What is the salary or compensation for this position?

This information is not specified in the job description.

What kind of work environment or company culture can I expect at Tailscale?

Tailscale is a fully distributed company with a fast-paced, startup-like environment that emphasizes rapid prototyping, iterative development with colleague and customer feedback, independent remote work, and community engagement.

What makes a strong candidate for this Software Engineer role?

Strong candidates have experience iteratively developing software in startup-like environments, excel at rapid prototyping, explaining technical concepts, and working directly with customers, even if they lack expertise in every area—highlight your strongest experiences and growth areas.

Tailscale

Secure VPN for remote resource access

About Tailscale

Tailscale offers a secure networking solution that allows users to access remote resources like virtual machines and databases from anywhere using a WireGuard-based Virtual Private Network (VPN). Its service is designed for businesses and individuals needing to manage private resources remotely, with a focus on simplicity and minimal setup. Tailscale's freemium model attracts a wide user base, allowing users to start for free and upgrade for additional features. The company aims to enhance data security while providing an easy-to-use remote access solution.

None, CanadaHeadquarters

2019Year Founded

$111.9MTotal Funding

SERIES_BCompany Stage

Enterprise Software, CybersecurityIndustries

51-200Employees

Benefits

Health Insurance

Dental Insurance

Vision Insurance

Flexible Work Hours

Remote Work Options

Unlimited Paid Time Off

Parental Leave

Professional Development Budget

Home Office Stipend

Phone/Internet Stipend

Company Equity

Risks

A critical vulnerability in Windows client poses remote code execution risk.

Cooling venture funding may impact Tailscale's future investment opportunities.

Scalability challenges may arise with rapid enterprise adoption of zero-trust solutions.

Differentiation

Tailscale uses WireGuard's Noise protocol for trusted encryption standards.

It integrates with existing identity providers like GSuite and Office365 for easy setup.

Tailscale offers over 100 integrations, fitting into almost any tech stack.

Upsides

Tailscale's zero-trust solution meets growing demand for enterprise security.

The $100 million Series B funding boosts product expansion and market reach.

Integration with Mullvad enhances privacy with a global VPN server network.

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