SEO & AI Optimization Generalist

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

We’re looking for a data-savvy, technically curious SEO & AI Optimization Generalist to help more people discover Tailscale—whether they’re searching on Google or prompting a large language model.

In this role, you’ll be responsible for growing discoverability and driving qualified traffic across both traditional and emerging search channels. You’ll bring analytical rigor and an experimentation mindset to continuously improve how our brand shows up in organic search, and increasingly, in AI-generated content and tools. This is a new, high-impact role where you’ll get to define best practices for LLM optimization as the ecosystem evolves.

You’ll work closely with web, content, and product marketing teams to optimize pages, shape content strategies, and measure what’s working (and what’s not). If you love diving into keywords, tinkering with structured data, running A/B tests, and thinking about how AI is reshaping search, this role is for you.

Key Responsibilities

Own and evolve our SEO strategy

• Conduct keyword research and competitive analysis to identify content opportunities across core Tailscale use cases.
• Partner with web and content teams to ensure SEO best practices are embedded in new and existing content, landing pages, and documentation.
• Manage and improve technical SEO elements—site structure, crawlability, canonical tags, schema markup, and more.
• Monitor organic traffic, keyword rankings, and page performance using tools like Google Search Console, GA4, and SEMRush.

Lead our LLM/AI discovery efforts

• Research how large language models (e.g. ChatGPT, Perplexity, Gemini) source and surface information.
• Experiment with techniques to increase Tailscale’s visibility in AI-generated responses, such as structuring content for retrieval, fine-tuning metadata, and strengthening topical authority.
• Track and report on AI-oriented metrics—mentions, citations, traffic from AI interfaces, and prompt results.

Analyze, experiment, and iterate

• Design and run A/B tests and SEO experiments to improve content engagement and conversion.
• Use analytics to uncover opportunities for optimization and provide actionable insights to content and marketing stakeholders.
• Help shape the future of web and content strategy by bringing performance data and LLM findings into broader planning conversations.

What We Are Looking For

SEO expertise

• 3–6 years experience in SEO within a B2B SaaS context, preferably within cybersecurity or networking.
• Deep understanding of on-page, off-page, and technical SEO.
• Familiarity with structured data and schema markup.
• Experience using SEMrush, Google Search Console, GA4, Surfer and related tools.

Emerging search and AI knowledge

• Working knowledge of how LLMs and generative AI models retrieve and surface information.
• Curiosity and creativity in experimenting with prompt outcomes, data structure, and discoverability across AI-native interfaces.

Performance analytics and experimentation

• Strong analytical mindset—able to define KPIs, build dashboards, and report insights clearly.
• Experience designing and running experiments across SEO and web funnels.
• Familiar with A/B testing and user engagement optimization tools like Mutiny, UserPilot, or similar.

Collaboration and project management

• Highly organized self-starter with strong attention to detail—able to manage multiple projects with clarity.
• Excellent communicator who can translate SEO and AI insights into clear, actionable ideas for non-technical stakeholders.
• Comfortable working cross-functionally across marketing, content, design, and engineering teams.

Nice to Have

• Experience using Looker to build and analyze performance dashboard.
• Experience optimizing for search on YouTube and/or Reddit.
• Experience working in a fully remote or distributed organization.
• Startup experience and/or track record of having impact at a startup.
• Has used and understands Tailscale.

As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. Tailscale's compensation package includes base salary, equity, and comprehensive benefits. The salary range displayed on each job posting represents the target range for a new hire's base salary. Individual offers may vary based on experience and skill set.

Frequently cited statistics show that people who identify with historically marginalized groups are likely to apply to jobs only if they meet 100% of the qualifications. We encourage you to help us break that statistic!

What We Offer

• 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!
• All-remote with the opportunity to work from anywhere—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).
• 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.