SEO & AI Optimization Generalist

📌 Core Information

🔹 Job Title: SEO & AI Optimization Generalist

🔹 Company: Tailscale

🔹 Location: Remote (United States)

🔹 Job Type: Full-time

🔹 Category: Marketing

🔹 Date Posted: April 8, 2025

🔹 Experience Level: Mid-level (5-10 years)

🔹 Remote Status: Remote (United States)

🚀 Job Overview

Key aspects of this role include:

• Developing and executing SEO strategies to drive organic traffic and brand visibility.
• Collaborating with cross-functional teams to optimize content, landing pages, and documentation for search engines.
• Managing technical SEO elements and ensuring site health and performance.
• Researching and experimenting with emerging search channels, such as large language models (LLMs) and AI-generated content.
• Analyzing data and reporting insights to inform content and marketing strategies.

ASSUMPTION: This role requires a balance of technical SEO expertise, analytical skills, and curiosity about emerging search trends. The ideal candidate will be comfortable working independently and collaborating with various teams to drive results.

📋 Key Responsibilities

✅ SEO Strategy & Execution: Own and evolve Tailscale’s SEO strategy, focusing on core use cases and competitive analysis.

✅ Content Optimization: Partner with web and content teams to ensure SEO best practices are embedded in new and existing content, landing pages, and documentation.

✅ Technical SEO Management: Oversee and improve technical SEO elements, such as site structure, crawlability, canonical tags, schema markup, and more.

✅ Organic Traffic Monitoring: Monitor organic traffic, keyword rankings, and page performance using tools like Google Search Console, GA4, and SEMrush.

✅ LLM/AI Discovery: Research how large language models source and surface information, and experiment with techniques to increase Tailscale’s visibility in AI-generated responses.

✅ Analytics & Experimentation: Design and run A/B tests and SEO experiments to improve content engagement and conversion, and use analytics to uncover optimization opportunities.

ASSUMPTION: This role requires a strong understanding of SEO best practices, experience with relevant tools, and a data-driven approach to decision-making. The ideal candidate will be comfortable working with both traditional and emerging search channels.

🎯 Required Qualifications

Education: Bachelor's degree in Marketing, Communications, or a related field (or equivalent experience).

Experience: 3-6 years of experience in SEO within a B2B SaaS context, preferably within cybersecurity or networking.

Required Skills:

• 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.
• Working knowledge of how LLMs and generative AI models retrieve and surface information.
• Strong analytical mindset and experience designing and running experiments across SEO and web funnels.
• Excellent communication skills and ability to collaborate effectively with cross-functional teams.

Preferred Skills:

• Experience using Looker to build and analyze performance dashboards.
• 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.

ASSUMPTION: The ideal candidate will have a proven track record in SEO, a strong analytical mindset, and a curiosity about emerging search trends. They should also be comfortable working independently and collaborating with various teams.

💰 Compensation & Benefits

Salary Range: $95,000 - $119,000 USD per year. This range represents the target range for a new hire's base salary and may vary based on experience and skill set.

Benefits:

• Comprehensive group benefits with no waiting period.
• Flexible paid time off program.
• Parental leave program with top-ups for up to 26 weeks.
• $1500 USD annually for professional development.
• Home office setup, including a company-owned laptop (Mac or PC), monthly home internet reimbursement, and $1000 USD to customize your workstation.
• All-remote work opportunities with the chance to work from anywhere and participate in virtual and in-person social events.
• Annual company retreat and team/department off-sites, or use of an individual travel budget to meet up with team members.

Working Hours: Full-time (40 hours per week) with flexible scheduling.

ASSUMPTION: Tailscale offers competitive compensation and benefits packages, with a focus on work-life integration and employee well-being. The salary range provided is an estimate based on industry standards for similar roles and experience levels.

📌 Applicant Insights

🔍 Company Context

Industry: Tailscale operates in the software development industry, focusing on secure and private networks for teams of any scale. The company was founded in 2019 and is headquartered in Toronto, Ontario, with additional offices in Berkeley, California.

Company Size: Tailscale is a mid-sized company with 51-200 employees, providing a collaborative and flexible work environment.

Founded: Tailscale was founded in 2019, focusing on simplifying secure network connectivity for teams.

Company Description:

• Tailscale makes it easy for teams to set up and manage secure, private networks without weeks of setup and configuration.
• The company offers a user-friendly alternative to traditional corporate VPNs, with no upfront cost, minimal latency, and compatibility with existing services.
• Tailscale is committed to maintaining fair and equitable compensation practices within its team across all roles and levels.

Company Specialties:

• Security
• Privacy
• Log Processing
• Connectivity
• Remote Access
• 2FA/MFA
• WireGuard
• Computer Networking
• Computer Networks
• VPN
• and SASE

Company Website: tailscale.com

ASSUMPTION: Tailscale is a well-established company in the software development industry, with a strong focus on security and privacy. The company values collaboration, flexibility, and work-life integration, offering competitive compensation and benefits packages to its employees.

📊 Role Analysis

Career Level: This role is at the mid-level (5-10 years) experience level, requiring a strong foundation in SEO and a curiosity about emerging search trends.

Reporting Structure: The SEO & AI Optimization Generalist will report directly to the Marketing team and collaborate closely with web, content, and product marketing teams.

Work Arrangement: This role is remote (United States) and offers flexible scheduling, allowing for a healthy work-life balance.

Growth Opportunities:

• As Tailscale continues to grow, there may be opportunities for the SEO & AI Optimization Generalist to take on more responsibilities or move into a management role.
• The ideal candidate will have the chance to shape the future of web and content strategy by bringing performance data and LLM findings into broader planning conversations.
• Tailscale offers professional development support, including $1500 USD annually for relevant training or certifications.

ASSUMPTION: This role offers significant growth potential for the right candidate, with opportunities to shape Tailscale’s SEO strategy and contribute to the company’s overall success.

🌍 Location & Work Environment

Office Type: Remote (United States)

Office Location(s): Tailscale has offices in Toronto, Ontario, and Berkeley, California, but this role can be performed remotely from anywhere in the United States.

Geographic Context:

• The United States offers a diverse range of living and working environments, from bustling cities to quiet rural areas.
• Tailscale’s remote work arrangement allows employees to live and work from anywhere in the country, providing flexibility and opportunities to explore new places.
• Tailscale’s company culture emphasizes collaboration and communication, ensuring that remote employees feel connected and engaged with the team.

Work Schedule: Full-time (40 hours per week) with flexible scheduling, allowing for a healthy work-life balance.

ASSUMPTION: Tailscale’s remote work arrangement offers employees the flexibility to work from anywhere in the United States, with a strong emphasis on collaboration and communication to ensure a positive work environment.

💼 Interview & Application Insights

Typical Process:

• Online application submission
• Phone or video screen with the hiring manager
• Technical assessment or case study
• Final interview with key stakeholders
• Background check and offer extension

Key Assessment Areas:

• SEO expertise and technical knowledge
• Analytical skills and data-driven decision-making
• Collaboration and communication skills
• Curiosity about emerging search trends and AI-generated content
• Alignment with Tailscale’s company culture and values

Application Tips:

• Tailor your resume and cover letter to highlight your SEO experience and relevant skills for this role.
• Be prepared to discuss your approach to SEO strategy, content optimization, and technical SEO management during the interview.
• Demonstrate your understanding of emerging search channels, such as LLMs and AI-generated content, and how you would approach optimizing for these platforms.
• Showcase your analytical skills and provide examples of how you have used data to inform SEO strategies and drive results in previous roles.
• Prepare questions to ask the interviewer about Tailscale’s company culture, work environment, and growth opportunities.

ATS Keywords: SEO, AI optimization, emerging search trends, LLM, generative AI, content optimization, technical SEO, analytics, collaboration, remote work, United States

ASSUMPTION: Tailscale’s interview process is designed to assess candidates’ technical SEO expertise, analytical skills, and cultural fit. The ideal candidate will be able to demonstrate their understanding of emerging search trends and provide concrete examples of their experience with SEO strategy, content optimization, and technical SEO management.

🛠️ Tools & Technologies

• SEMrush
• Google Search Console
• GA4
• Surfer
• Looker (nice to have)
• Large language models (e.g., ChatGPT, Perplexity, Gemini)
• Structured data and schema markup tools
• Mutiny or similar A/B testing tools
• UserPilot or similar user engagement optimization tools

ASSUMPTION: The ideal candidate will have experience with relevant SEO tools, such as SEMrush, Google Search Console, GA4, and Surfer. Familiarity with Looker, Mutiny, or similar tools is a plus but not required.

👔 Cultural Fit Considerations

Company Values:

• Simplicity
• Security
• Privacy
• Collaboration
• Flexibility
• Work-life integration

Work Style:

• Remote-friendly and flexible work arrangements
• Data-driven decision-making and continuous learning
• Collaborative and inclusive team environment
• Focus on results and impact over hours worked
• Strong emphasis on work-life integration and employee well-being

Self-Assessment Questions:

• Do you thrive in a remote work environment and enjoy the flexibility it offers?
• Are you comfortable working independently and collaborating with cross-functional teams?
• Do you have a strong analytical mindset and enjoy using data to inform decision-making?
• Are you curious about emerging search trends and eager to experiment with new optimization techniques?
• Do you align with Tailscale’s company values, particularly simplicity, security, privacy, and collaboration?

ASSUMPTION: Tailscale values candidates who are comfortable working remotely, have a strong analytical mindset, and are curious about emerging search trends. The ideal candidate will also align with the company’s values and be able to thrive in a collaborative and inclusive team environment.

⚠️ Potential Challenges

• Working remotely may require strong self-motivation and time management skills.
• Keeping up with emerging search trends and AI-generated content may be challenging, as the landscape is constantly evolving.
• Collaborating effectively with cross-functional teams may require strong communication and project management skills.
• Managing technical SEO elements and ensuring site health and performance may be technically demanding at times.
• Working in a fully remote environment may limit opportunities for in-person networking and collaboration.

ASSUMPTION: The ideal candidate will be able to overcome these challenges by demonstrating strong self-motivation, time management, communication, and technical skills. They will also be comfortable working remotely and eager to stay up-to-date with emerging search trends and AI-generated content.

📈 Similar Roles Comparison

• Unlike traditional SEO roles, this position requires a strong understanding of emerging search channels, such as large language models and AI-generated content.
• Tailscale’s focus on security and privacy sets it apart from other companies in the software development industry.
• This role offers significant growth potential, as Tailscale continues to expand its team and product offerings.
• Tailscale’s remote work arrangement provides flexibility and opportunities to work from anywhere in the United States.

ASSUMPTION: This role is unique in its focus on emerging search channels and Tailscale’s commitment to security and privacy. The ideal candidate will be able to leverage their SEO expertise and curiosity about emerging trends to drive results and contribute to the company’s overall success.

📝 Sample Projects

• Developing and executing an SEO strategy to drive organic traffic and brand visibility for Tailscale’s core use cases.
• Optimizing content, landing pages, and documentation for search engines, ensuring that Tailscale’s brand is prominently featured in relevant search results.
• Researching and experimenting with emerging search channels, such as large language models and AI-generated content, to identify new optimization opportunities.
• Analyzing data and reporting insights to inform content and marketing strategies, driving continuous improvement in Tailscale’s SEO performance.

ASSUMPTION: These sample projects illustrate the breadth of responsibilities for the SEO & AI Optimization Generalist role at Tailscale. The ideal candidate will be able to demonstrate their experience with similar projects and provide concrete examples of their approach to SEO strategy, content optimization, and technical SEO management.

❓ Key Questions to Ask During Interview

• Can you describe the typical SEO strategy for a B2B SaaS company like Tailscale, and how it might differ for emerging search channels like LLMs and AI-generated content?
• How does Tailscale approach collaboration and communication in a remote work environment, and what tools do you use to facilitate teamwork?
• Can you provide an example of a successful SEO campaign you’ve led in the past, and how you measured its impact on organic traffic and brand visibility?
• How does Tailscale ensure that its website and content are secure and private, and what role does the SEO & AI Optimization Generalist play in maintaining these standards?
• What opportunities are there for professional development and growth within the SEO & AI Optimization Generalist role, and how does Tailscale support its employees in achieving their career goals?

ASSUMPTION: These key questions are designed to help the ideal candidate understand the nuances of the SEO & AI Optimization Generalist role at Tailscale and assess their fit with the company’s culture and values.

📌 Next Steps for Applicants

To apply for this position:

• Submit your application through Tailscale’s careers page.
• Tailor your resume and cover letter to highlight your SEO experience and relevant skills for this role.
• Prepare for your interview by researching Tailscale’s company culture, values, and products, and be ready to discuss your approach to SEO strategy, content optimization, and technical SEO management.
• If selected for an interview, be prepared to provide examples of your experience with SEO strategy, content optimization, and technical SEO management, as well as your understanding of emerging search channels and AI-generated content.
• Follow up with the hiring manager after your interview to express your interest in the role and reiterate your qualifications.

⚠️ This job description contains AI-assisted information. Details should be verified directly with the employer before making decisions.