Technical Content Specialist at Tailscale - Remote Canada — Columbus

About Tailscale

Tailscale is making safe connection effortless 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.

About the Role

We're looking for a Technical Growth Content Specialist to create educational content that helps enterprise buyers and technical practitioners discover, evaluate, and adopt Tailscale.

This role sits at the intersection of technical writing, content marketing, developer education, and product storytelling. Working closely with the AI & Organic Search Manager, you'll transform customer questions, product launches, search insights, and emerging industry trends into technically accurate content that performs across traditional search engines and AI-powered discovery platforms (ChatGPT, Gemini, AI Overviews), and the social channels where technical audiences discover tools today.

Success isn't measured by how much content you publish — it's measured by the quality, usefulness, and business impact of the content you create. You'll build with the product, collaborate with technical subject matter experts, and create tutorials, implementation guides, comparison pages, demos, and educational resources that earn trust with enterprise audiences and support Tailscale's growth.

We're looking for someone who has made a significant impact on metrics as a content writer. This is a growth-centered position that will be accountable for specific metrics each quarter.

Key Responsibilities

• Create hyper-relevant content that drives measurable growth by turning search insights, customer questions, and real-time community signals into high-impact content.
• Monitor conversations across Twitter, Hacker News, and Reddit, and turn emerging questions and trends into timely content — often same-week, sometimes same-day.
• Partner with the AI & Organic Search Manager to turn discoverability opportunities into high-impact content.
• Build hands-on experience with Tailscale to create credible, practical technical content.
• Produce content at a high velocity while maintaining a high bar for technical accuracy and editorial quality.
• Partner with Product Marketing, Product, Engineering, Developer Relations, Docs, and subject matter experts to ensure content is accurate and useful.
• Refresh, expand, and optimize existing content based on performance insights and customer feedback.
• Develop an AI-first content program that turns search, customer, product, and performance insights into high-quality content faster.
• Support strategic initiatives with technical content that drives metrics like self-serve revenue and product adoption.

What We Are Looking For

• 3–6+ years of experience in growth technical content marketing, technical writing, developer marketing, journalism, or a related field
• Exceptional writing and editing skills with the ability to explain complex technical concepts clearly
• Familiarity with SEO and AI discoverability best practices
• Highly curious with a hunger to learn and jump head-first into tough challenges
• Experience creating educational content for technical or enterprise audiences
• Comfortable learning new technologies and building with products to create authentic technical content
• Experience using AI tools to research, draft, and improve content quality and production speed
• Strong collaboration skills and the ability to work closely with engineering, product, and marketing teams
• Excellent project management and organizational skills

Nice to Have

• Experience marketing developer tools, infrastructure, networking, cybersecurity, or B2B SaaS products
• Familiarity with GitHub, Markdown, HTML, or static site generators
• Experience building sample applications, demos, or interactive technical resources
• Basic familiarity with scripting or programming languages such as Python, JavaScript, or Go
• Experience creating videos, diagrams, or other technical educational content
• An active presence in developer communities through writing, speaking, open source, or personal projects
• An existing audience on Twitter/X, or a personal blog in the AI space
• Experience building content clusters that drive topical authority and compounding growth

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.

CAN Pay Range
$127,300 — $159,460 CAD

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. 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. 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.
• Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
• Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore.
• Support for your personal and professional development. $1,500 USD annually for professional development, plus 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.
• A build-your-own home office setup. Choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation.
• Paid parental leave program. 20 weeks for birthing parents, 16 weeks for non-birthing parents.

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.

Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.