Software Engineer (Identity), Product Strategy

📍 Job Overview

Job Title: Software Engineer (Identity), Product Strategy
Company: Tailscale
Location: Remote (Canada)
Job Type: Full-time
Category: Product Strategy / Software Engineering / Identity & Access Management
Date Posted: October 6, 2025
Experience Level: Mid-Level (2-5 years suggested)
Remote Status: Fully Remote

🚀 Role Summary

• Drive product strategy for Tailscale's identity and connectivity solutions by building compelling proof-of-concepts (POCs) and integrating with customer workflows.
• Act as a technical liaison, working directly with customers to demonstrate how Tailscale's identity-aware networking and secure connectivity solve critical business problems.
• Develop and articulate reference architectures, technical documentation, and community engagement strategies to showcase Tailscale's value proposition.
• Leverage expertise in identity protocols, access control models, and modern programming languages to build and validate production-ready code.

📝 Enhancement Note: This role bridges product strategy with hands-on engineering, focusing on the practical application and integration of Tailscale's identity and connectivity features. The emphasis on customer interaction and POC development suggests a strong need for communication skills alongside technical proficiency. The "Product Strategy" title implies a forward-looking role, contributing to the roadmap and market positioning of Tailscale's identity offerings.

📈 Primary Responsibilities

• Develop and maintain proof-of-concept (POC) projects that highlight Tailscale's capabilities for AI agents, tooling (e.g., MCP gateways, remote servers), and advanced identity use cases.
• Collaborate closely with customers to integrate Tailscale into their environments, serving as a technical advisor for both internal adoption (e.g., VPN replacement, identity-aware networking) and embedding Tailscale into their customer-facing products for secure connectivity.
• Design and document comprehensive reference architectures that illustrate best practices for utilizing Tailscale in diverse deployment scenarios.
• Engage with the developer community through documentation, blog posts, presentations, and direct interaction to foster adoption and gather feedback.
• Validate and secure code for production use, working in conjunction with security teams to ensure robust and reliable identity and access control implementations.
• Utilize daily experience with Large Language Models (LLMs) to inform development and build innovative tools and applications on top of these AI capabilities.
• Troubleshoot and resolve technical challenges encountered during customer integrations and POC development, ensuring a smooth and effective user experience.

📝 Enhancement Note: The responsibilities emphasize a blend of proactive development (POCs, reference architectures) and reactive customer engagement (integrations, troubleshooting). The inclusion of AI/LLM work is a significant differentiator, requiring candidates to be at the forefront of emerging technologies.

🎓 Skills & Qualifications

Education: While no specific degree is mandated, a strong foundation in Computer Science, Software Engineering, or a related technical field is highly recommended. Practical experience and demonstrated skills will be prioritized over formal education.
Experience: Minimum of 2-5 years of professional experience in software development, with a significant focus on identity systems, access control, and/or secure networking. Experience in a customer-facing or technical advocacy role is a strong plus.

Required Skills:

• Proven ability in rapid prototyping and building functional proof-of-concepts.
• Excellent communication skills for explaining complex technical concepts clearly and concisely to both technical and non-technical audiences.
• Demonstrated experience working directly with customers to understand their needs and guide them through technical integrations.
• In-depth knowledge of authentication protocols, including OAuth, OIDC, SAML, and SCIM.
• Solid understanding of identity infrastructure concepts, such as Identity Provider (IdP) platforms, identity synchronization/provisioning, and directory services.
• Proficiency in access control models, including Role-Based Access Control (RBAC) and Attribute-Based Access Control (ABAC), as well as session management, Multi-Factor Authentication (MFA), and passwordless authentication.
• Strong technical skills in Go and/or Python; familiarity with TypeScript is a valuable asset.
• Experience with third-party API integrations and understanding of basic networking principles.
• Practical experience in using LLMs daily for planning and development, with the ability to build tools and applications leveraging LLM capabilities.
• Experience in validating code for secure production use with security teams.
• Ability to thrive and work independently in a fully remote environment, managing time effectively and maintaining high productivity.

Preferred Skills:

• Direct familiarity with Tailscale networking solutions and concepts.
• Experience with agentic AI tools and an understanding of their associated security considerations.
• Background in developing or supporting developer tooling.
• Understanding of networking challenges prevalent in multi-cloud and hybrid deployment environments.
• Active participation or contribution to open-source communities.

📝 Enhancement Note: The "What We Are Looking For" section explicitly states that expertise in every listed qualification is not required, encouraging candidates to highlight their strongest areas. This suggests a flexible hiring approach, valuing potential and a willingness to learn alongside existing skills.

📊 Process & Systems Portfolio Requirements

Portfolio Essentials:

• Showcase of at least 2-3 robust proof-of-concept (POC) projects demonstrating practical application of identity protocols (OAuth, OIDC, SAML, SCIM) or access control models (RBAC, ABAC).
• Examples of customer integrations or technical advisory engagements, highlighting problem-solving and solution implementation for secure connectivity or identity management.
• Documentation of reference architectures or technical guides related to networking, identity infrastructure, or API integrations.
• Evidence of code contributions (e.g., GitHub profile) demonstrating proficiency in Go, Python, or TypeScript, particularly in areas related to security, networking, or AI/LLM applications.
• Demonstrations of experience with AI/LLM tools, including any custom-built applications or workflows.

Process Documentation:

• Detailed explanations of how you approach the development lifecycle for POCs, from ideation and technical design to implementation and validation.
• Examples of how you have documented technical processes, such as API integration guides, security protocols for identity systems, or best practices for network configuration.
• Case studies illustrating how you have worked with customers to define, implement, and troubleshoot complex technical integrations, emphasizing process efficiency and user adoption.

📝 Enhancement Note: Given the role's focus on product strategy and customer engagement, a portfolio should emphasize not just technical skills but also the ability to translate technical capabilities into tangible solutions and clear documentation. The AI/LLM component is critical and should be well-represented.

💵 Compensation & Benefits

Salary Range: $191,620 - $302,840 CAD per year.
Benefits:

• Comprehensive group benefits with no waiting period, including health, vision, and dental coverage for employees and their families.
• Equity incentive plan, providing ownership in Tailscale's growth.
• Generous parental leave program with top-ups for up to 26 weeks from the first day of employment.
• $1500 USD annually for professional development, supporting continuous learning and skill enhancement.
• Corporate co-working program for access to spaces like WeWork.
• $1000 USD allowance for home office setup, plus company-provided laptop (Mac or PC) and monthly internet reimbursement.
• Flexible, paid time off program designed to support work-life integration.
• Annual company retreat, team/department off-sites, and an individual travel budget for in-person team meetups.

Working Hours: Tailscale operates on a 40-hour work week, with a strong emphasis on flexibility to support work-life integration and remote work.

📝 Enhancement Note: The provided salary range is specific to Canada. The benefits package is extensive, with a strong focus on employee well-being, professional growth, and remote work enablement, aligning with the company's remote-first culture.

🎯 Team & Company Context

🏢 Company Culture

Industry: Cloud Infrastructure, Cybersecurity, Networking, SaaS. Tailscale operates in a rapidly evolving market focused on simplifying secure network access and identity management for distributed teams and applications.
Company Size: Tailscale is a well-funded, growing startup. While the exact number of employees isn't stated, the mention of backing from prominent venture capital firms (Accel, CRV, Insight, Heavybit, Uncork Capital) and a fully distributed model suggests a dynamic, agile environment with significant growth potential.
Founded: 2019. This indicates a relatively young company that has quickly established itself in the market, implying a culture of innovation, speed, and adaptability.

Team Structure:

• The Product Strategy team reports directly to the Chief Strategy Officer, suggesting a high level of visibility and influence.
• This role will likely involve close collaboration with engineering, product management, sales, and customer success teams.
• As a fully distributed company, collaboration heavily relies on digital tools and asynchronous communication, fostering a culture of documentation and clarity.

Methodology:

• Tailscale emphasizes a "new Internet" approach, focusing on ease of use, security, and sensible design for connectivity.
• The company culture values independent work, adaptability, and a forward-thinking mindset, particularly with its focus on AI and LLMs.
• A strong emphasis is placed on diversity and inclusion, encouraging individuals from historically marginalized groups to apply.

Company Website: https://tailscale.com/

📝 Enhancement Note: Tailscale's distributed-first model, coupled with its focus on innovation (AI/LLMs) and inclusive culture, shapes a unique work environment that appeals to self-motivated professionals who value autonomy and impact.

📈 Career & Growth Analysis

Operations Career Level: This role is positioned as a Software Engineer within Product Strategy, indicating a mid-level to senior individual contributor role. It's not a traditional "operations" role in the sense of Sales Ops or Rev Ops, but rather an engineering role focused on product application and market strategy, particularly in the identity and connectivity space.
Reporting Structure: The role reports directly to the Chief Strategy Officer. This is a highly visible reporting line, offering direct access to senior leadership and strategic decision-making processes.
Operations Impact: While not a direct revenue operations role, this position significantly impacts revenue by demonstrating Tailscale's value proposition, driving adoption through POCs and integrations, and contributing to product strategy. Success in this role directly correlates with customer acquisition, retention, and the overall market success of Tailscale's identity offerings.

Growth Opportunities:

• Technical Specialization: Deepen expertise in identity protocols, access control, secure networking, and AI/LLM development within a cutting-edge product.
• Product Strategy Influence: Contribute directly to the product roadmap and market positioning of Tailscale's core offerings.
• Customer Advocacy & Thought Leadership: Develop a reputation as an expert through customer engagement, documentation, and community contributions.
• Leadership Potential: Opportunities to lead technical initiatives, mentor junior engineers, and potentially transition into product management or technical leadership roles.
• Cross-functional Exposure: Gain broad experience working with various departments, from engineering to sales and marketing.

📝 Enhancement Note: The direct reporting to the CSO is a significant indicator of the role's strategic importance and potential for high-impact contributions and rapid career progression within Tailscale.

🌐 Work Environment

Office Type: Fully Remote. Tailscale is a remote-first company, offering significant flexibility in where employees work.
Office Location(s): While fully remote, the role is specifically for candidates located in Canada. The company also has a presence and supports employees in the United States and the United Kingdom, with options for virtual and in-person social events and a corporate co-working program.

Workspace Context:

• Collaboration is primarily digital, utilizing various communication and project management tools.
• Emphasis on asynchronous communication and thorough documentation to bridge geographical distances.
• A supportive remote setup includes a company-provided laptop, home office allowance, and internet reimbursement.
• Opportunities exist to connect with colleagues in person through company retreats, off-sites, and team meetups.

Work Schedule: The standard work week is 40 hours, but Tailscale emphasizes flexibility to promote work-life integration. This allows individuals to structure their days to optimize productivity and personal well-being, a key aspect for a remote-first company.

📝 Enhancement Note: The "remote first" approach means the work environment is designed around digital collaboration, autonomy, and employee well-being, rather than a traditional office setting.

📄 Application & Portfolio Review Process

Interview Process:

• Initial Screening: A review of your application and resume to assess alignment with core requirements, particularly experience in identity systems, programming languages, and customer interaction.
• Technical Interview(s): Expect in-depth discussions on your experience with authentication protocols, access control, Go/Python development, and AI/LLM usage. This may include live coding exercises or deep dives into past projects.
• POC/Portfolio Review: You will likely be asked to present a relevant proof-of-concept or portfolio piece that showcases your ability to build, integrate, and explain technical solutions, especially those related to identity and connectivity.
• Customer/Strategy Discussion: An interview focused on your approach to customer engagement, problem-solving, and how you would contribute to product strategy in the identity space.
• Cultural Fit & Values Interview: Assessment of your ability to thrive in a remote, independent, and collaborative environment, aligning with Tailscale's company values.

Portfolio Review Tips:

• Showcase Impact: Prioritize projects that demonstrate tangible results or clear problem-solving capabilities, especially those involving identity, security, or complex integrations.
• Highlight Process: Clearly articulate the problem you were solving, your technical approach, the tools/languages used (Go, Python, AI/LLMs), and the outcome or learnings.
• Customer-Centric Examples: If possible, include examples of how you've guided users or customers through technical challenges or integrations.
• Code Samples: Provide links to well-documented code repositories (e.g., GitHub) that demonstrate your proficiency in required languages and technologies.
• AI/LLM Integration: Clearly explain how you've leveraged LLMs in your work, whether for development assistance, building applications, or solving specific problems.

Challenge Preparation:

• Technical Depth: Be prepared to discuss advanced concepts in OAuth, OIDC, SAML, SCIM, RBAC, ABAC, and secure coding practices.
• Problem-Solving Scenarios: Anticipate questions that require you to architect a solution for a specific identity or connectivity challenge Tailscale might face.
• Communication Skills: Practice explaining complex technical details concisely and persuasively, as you'll be interacting with customers and internal stakeholders.

📝 Enhancement Note: The interview process will likely be rigorous, focusing on both deep technical expertise and the ability to apply that knowledge in a customer-facing, product-oriented capacity, with strong emphasis on portfolio demonstration.

🛠 Tools & Technology Stack

Primary Tools:

• Programming Languages: Go and Python are primary requirements; TypeScript is a valuable asset.
• Identity & Access Management: Deep understanding and practical experience with OAuth, OIDC, SAML, SCIM, RBAC, ABAC, MFA, and passwordless authentication.
• Infrastructure: Familiarity with IdP platforms, identity sync/provisioning, and directory services.
• AI/LLMs: Daily use for planning and development; comfort building tools and applications on top of LLMs.

Analytics & Reporting:

• While not explicitly detailed, expect to use tools for tracking POC effectiveness, customer integration success, and technical issue resolution. This could involve internal dashboards or project management tools.

CRM & Automation:

• Experience with third-party API integrations is crucial for connecting Tailscale with various customer systems.
• While not a direct CRM role, understanding how identity systems integrate with CRM and other business applications is beneficial.
• Automation tools may be used for CI/CD pipelines, testing, and workflow management in POC development.

📝 Enhancement Note: The core technology stack revolves around identity protocols, modern programming languages (Go, Python), and AI/LLMs, all within the context of secure networking and cloud infrastructure.

👥 Team Culture & Values

Operations Values:

• Innovation & Prototyping: A strong drive to build, experiment, and create tangible solutions, especially with new technologies like AI/LLMs.
• Customer Focus: Dedication to understanding and solving customer problems through effective technical integration and support.
• Security & Reliability: A commitment to building robust, secure, and production-ready systems, validated by security teams.
• Independence & Autonomy: Trust and empowerment for individuals to manage their work effectively in a remote environment.
• Inclusivity & Diversity: A culture that values diverse voices and backgrounds, fostering an equitable environment for all team members.

Collaboration Style:

• Asynchronous Communication: Reliance on clear, documented communication to facilitate collaboration across time zones and geographies.
• Cross-Functional Partnership: Working closely with engineering, product management, and customer-facing teams to align on strategy and execution.
• Community Engagement: Active participation in sharing knowledge and best practices with the broader developer community.
• Feedback-Driven: Openness to feedback from customers and colleagues to continuously improve solutions and processes.

📝 Enhancement Note: Tailscale's culture emphasizes a blend of individual contribution and collaborative problem-solving, underpinned by a strong commitment to its core values, especially in a remote setting.

⚡ Challenges & Growth Opportunities

Challenges:

• Rapidly Evolving Landscape: Staying ahead of advancements in identity management, cybersecurity, and AI/LLM technologies.
• Customer Integration Complexity: Navigating diverse technical environments and unique customer needs to ensure successful Tailscale integrations.
• Balancing POC Development with Customer Support: Effectively managing time between building forward-looking prototypes and addressing immediate customer integration needs.
• Remote Collaboration Dynamics: Maintaining strong team cohesion and effective communication in a fully distributed work environment.
• Security Validation: Ensuring all developed code and integrations meet stringent security standards required for production environments.

Learning & Development Opportunities:

• Deep Dive into Identity & Security: Become an expert in cutting-edge identity protocols, access control mechanisms, and secure network architecture.
• AI/LLM Application: Gain hands-on experience building real-world applications and tools leveraging AI technologies.
• Product Strategy Contribution: Influence the direction of Tailscale's product offerings and gain strategic market insights.
• Customer Engagement Skills: Enhance abilities in technical consultation, solution selling, and relationship building with enterprise clients.
• Remote Work Mastery: Develop best practices for effective communication, time management, and productivity in a distributed team setting.

📝 Enhancement Note: The challenges presented are opportunities for significant professional growth, particularly in areas critical to modern software development and business strategy.

💡 Interview Preparation

Strategy Questions:

• "Describe a complex identity system you've worked on. What were the key challenges, and how did you overcome them?" (Focus on protocols, access control, Go/Python, and problem-solving.)
• "How would you build a POC to demonstrate Tailscale's value for securing AI agent access to internal resources?" (Prepare to outline architecture, key components, and potential customer benefits.)
• "Imagine a customer wants to embed Tailscale for secure customer-to-customer connectivity in their SaaS product. What are the key considerations and integration steps you'd discuss?" (Demonstrate understanding of customer-facing integrations and technical advisory.)

Company & Culture Questions:

• "Why are you interested in Tailscale and our mission to build a new Internet?" (Research Tailscale's product, market position, and values.)
• "How do you approach working independently in a remote team environment? What strategies do you use to stay productive and connected?" (Highlight self-management, communication, and collaboration skills.)
• "How do you see AI/LLMs evolving the future of identity and secure connectivity?" (Show passion for emerging tech and how it applies to Tailscale's domain.)

Portfolio Presentation Strategy:

• Structured Narrative: For each portfolio piece, clearly state the problem, your solution (technical approach, languages, tools), and the outcome or learnings.
• Visual Aids: Use diagrams, code snippets, or demo recordings to effectively illustrate your points.
• Focus on Impact: Emphasize the value your work brings, whether it's enhanced security, improved efficiency, or a solved customer problem.
• Technical Depth: Be ready to dive into the technical details of your implementations, especially regarding identity protocols and programming languages.
• Customer Empathy: Frame your solutions in terms of how they benefit users or customers.

📝 Enhancement Note: Preparation should focus on demonstrating a strong technical foundation, excellent communication, customer-centric problem-solving, and a forward-thinking approach to identity and connectivity, with a clear understanding of Tailscale's mission.

📌 Application Steps

To apply for this Software Engineer (Identity), Product Strategy position:

• Submit your application through the provided Greenhouse link.
• Tailor Your Resume: Emphasize experience with identity protocols (OAuth, OIDC, SAML, SCIM), access control (RBAC, ABAC), programming languages (Go, Python), and AI/LLM applications. Quantify achievements where possible.
• Curate Your Portfolio: Select 2-3 strong examples of POCs, integrations, or technical documentation that best showcase your relevant skills. Prepare to present these concisely, focusing on problem, solution, and impact.
• Prepare for Technical Deep Dives: Brush up on core concepts in identity management, secure networking, and your preferred programming languages. Be ready to discuss your experience with AI/LLM tools.
• Research Tailscale: Understand their product, mission, recent news, and company values. Prepare thoughtful questions to demonstrate your interest and engagement.

⚠️ Important Notice: This enhanced job description includes AI-generated insights and operations industry-standard assumptions. All details should be verified directly with the hiring organization before making application decisions.

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