Content Marketing Specialist, Tailscale
CA$158.1-198.3k
+ Equity
A zero config VPN for building secure networks
Be an early applicant
A zero config VPN for building secure networks
201-500 employees
Be an early applicant
CA$158.1-198.3k
+ Equity
201-500 employees
Company mission
To remove overhead and complexity from the “long tail” of software and operational problems that people face every day.
Role
Who you are
- 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
- 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 the job involves
- 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
- 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
Our take
The internet is a global phenomenon, but often online activity is unprotected which leaves users vulnerable to hackers on public networks. Additionally certain sites are inaccessible or censored depending on the users location. Use of a VPN enables a secure connection through an encrypted virtual tunnel which also disguises IP addresses. Traditional VPN's tunnel all network traffic through a central gateway server which can affect reliability, and VPN's almost always slow connection speed.
Tailscale is a VPN service built on top of a secure network fabric, which is unlike a traditional VPN provider as it ensures encrypted point-to-point connections by using the open source WireGuard protocol. Tailscale is configured, on average, in a matter of minutes, while other solutions take weeks to fully implement and then require several hours a week of maintenance.
The product has been well received, with reviewers agreeing that it is easy to set up and a great tool for developers. The company plans to develop its product further by tackling the complexity of software and confronting operational problems that people face daily. Off the back of impressive 2025 funding, Tailscale is expanding its engineering, product and sales teams as well as its global reach, all to empower small teams to build systems that scale, without scaling overhead.
Steph
Company Specialist at Welcome to the Jungle
Insights
81% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Apr 2025
$160m
SERIES C
May 2022
$100m
SERIES B
Total funding: $275m
Company benefits
- Flexible (and reasonable) working hours—work/life balance is exceptionally important to us
- Competitive compensation, stock options and 401(k) (for United States-based employees)
- Comprehensive medical/dental/vision benefits, and more
- 4 weeks of paid vacation (standard across the company) + 12 company holidays per year
- An allowance for equipment to help you personalize your workspace
Company HQ
King West Village, Toronto, ON
Leadership
Avery Pennarun
(Co-Founder & CEO)A range of experience in software engineering including Senior Staff Software Engineer at Google Fiber. They co-founded EQL Data in 2009.
David Crawshaw
(Co-Founder & CTO)Previous experience includes working as a Staff Software Engineer at Google before co-founding Tailscale.
David Carney
(Co-Founder)Co-founded Format in 2012, working as a Full Stack Developer, COO and CFO. Also co-founded Form & Method and The Navarra Group.
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