Calling the bold.

Calling the bold.

Uncork-backed companies are hiring explorers, builders, and operators ready to help chart new territory.

Uncork-backed companies are hiring explorers, builders, and operators ready to help chart new territory.

Content Marketing Specialist

Tailscale

Tailscale

Marketing & Communications
Canada · Remote
CAD 158,120-198,320 / year + Equity
Posted on Feb 2, 2026

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 technical and experienced Content Marketing Specialist to join the marketing team at Tailscale. You will be working closely with sales, product marketing, and other marketing teams to transform product positioning and messaging into content. This role will be a good fit if you’re familiar with networking infrastructure, developer tooling, or enterprise security needs, and can communicate technical features as easy-to-digest benefits. Because we’re an early-stage and fully remote company, we’re looking for an individual who is comfortable working asynchronously and thrives in ambiguity.

Key Responsibilities

  • Participate in the development and refinement of product positioning and messaging, then synthesize it into effective content for a technical audience.
  • Collaborate with sales, product marketing, growth marketing, web development, design, and more to identify, develop, and produce effective content.
  • Become an expert on our users and customers, understanding who they are, their pain points, etc.
  • Create purposeful content that convinces and helps drive sales, including but not limited to: landing pages, one-pagers, case studies, slide decks, white papers, blog posts, ad copy, and more.
  • Position Tailscale as a thought leader in networking and security, and increase awareness of these issues through impactful content.

What We Are Looking For

  • A strong writing background as a content writer, with a fluency in the tech industry and highly technical subject matters like networking, Kubernetes, etc.
  • Experience with solutions at B2B or enterprise technology companies
  • Experience with networking or security products used in SaaS or cloud environments
  • A proven track record of collaborating with marketing, product marketing, sales enablement, product management, or a related field
  • Impeccable writing and editing skills, with participation in feedback cycles being second nature
  • Ability to adhere to an overall content strategy, product messaging, and product positioning in the work you produce
  • Comfortable working on multiple work streams simultaneously, juggling different stakeholders and deadlines
  • Experience with on-page SEO and AEO optimization
  • Excellent people skills, including the ability to communicate and negotiate effectively

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 Ranges
$158,120$198,320 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. 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!
  • 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). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
  • 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.

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.