Customer Support Engineer | Tailscale | Remote (Canada)
Posted 2025-09-08
Remote, USA
Full Time
Immediate Start
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">About Tailscale</strong></p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">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.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">Job Description</strong></p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">If you’re passionate about solving networking issues and providing high-quality support, this is the role for you! We’re seeking a new full-time Customer Support Engineer to join our growing team. In this role, you will be responsible for providing technical support for individuals, teams, and companies using Tailscale. You’ll be part of a growing team of engineers focused on delivering excellent support and proactively solving friction through partnering with our Sales, Product, and Engineering teams.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">Because we’re an early-stage and fully remote company, we’re looking for a motivated individual who can think on their feet, enjoys collaborating with highly technical teams, and is comfortable working asynchronously. This doesn’t mean we are going to give you more work than you can handle – we want to understand your special, niche skills and enable you to bring them to work with you.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">Key Responsibilities:</strong></p>
<ul class=" text-base sm:text-lg marker:text-color list-inside list-disc text-gray-500 list-disc list-outside pl-3 mb-6">
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Become an expert in the use of the Tailscale product, including Access Control, Authentication, and Routing features</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Handle support requests from customers regarding issues occurring in their use of the product</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Work closely with Customer Success, Sales, and Engineering to help users successfully deploy the Tailscale product</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Collaborate with our Engineering team to debug and fix customer issues</span></li>
</ul>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">Requirements:</strong></p>
<ul class=" text-base sm:text-lg marker:text-color list-inside list-disc text-gray-500 list-disc list-outside pl-3 mb-6">
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">4+ years experience in technical support roles</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">1+ years experience with networking. You should know what a subnet is and what routing does. CCNA or equivalent is a plus. Extensive experience with Tailscale is even better</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Interpersonal communication skills and the ability to work effectively on a team</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Excellent written communication skills. Much of the role is via email and forum-based conversations</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">A strong desire to work with customers and partners in solving problems</span></li>
</ul>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. We use San Francisco market data to establish our pay ranges.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">CAN Pay Ranges</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">$129,980—$162,140 CAD</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><em>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.</em> <strong class=" font-semibold"><em>We encourage you to help us break that statistic!</em></strong></p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">What We Offer</strong></p>
<ul class=" text-base sm:text-lg marker:text-color list-inside list-disc text-gray-500 list-disc list-outside pl-3 mb-6">
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200"><strong class=" font-semibold">An inclusive, flexible environment where you can be your authentic self.</strong> 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.</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200"><strong class=" font-semibold">A competitive total compensation package.</strong> This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200"><strong class=" font-semibold">Comprehensive group benefits with no waiting period.</strong> Take advantage of coverage for health, vision, dental, and more for you and your family!</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200"><strong class=" font-semibold">All-remote with the opportunity to work from anywhere</strong>—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).</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200"><strong class=" font-semibold">Connect with other Tailscalars IRL.</strong> 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.</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200"><strong class=" font-semibold">Support for your personal and professional development.</strong> Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200"><strong class=" font-semibold">Paid time off and a healthy work-life integration.</strong> Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world! We encourage all Tailscalars to take 4-6 weeks of vacation annually**.**</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200"><strong class=" font-semibold">A build-your-own home office setup.</strong> 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.</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200"><strong class=" font-semibold">Generous parental leave program from your first day.</strong> 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.</span></li>
</ul>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">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.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">Job Description</strong></p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">If you’re passionate about solving networking issues and providing high-quality support, this is the role for you! We’re seeking a new full-time Customer Support Engineer to join our growing team. In this role, you will be responsible for providing technical support for individuals, teams, and companies using Tailscale. You’ll be part of a growing team of engineers focused on delivering excellent support and proactively solving friction through partnering with our Sales, Product, and Engineering teams.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">Because we’re an early-stage and fully remote company, we’re looking for a motivated individual who can think on their feet, enjoys collaborating with highly technical teams, and is comfortable working asynchronously. This doesn’t mean we are going to give you more work than you can handle – we want to understand your special, niche skills and enable you to bring them to work with you.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">Key Responsibilities:</strong></p>
<ul class=" text-base sm:text-lg marker:text-color list-inside list-disc text-gray-500 list-disc list-outside pl-3 mb-6">
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Become an expert in the use of the Tailscale product, including Access Control, Authentication, and Routing features</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Handle support requests from customers regarding issues occurring in their use of the product</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Work closely with Customer Success, Sales, and Engineering to help users successfully deploy the Tailscale product</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Collaborate with our Engineering team to debug and fix customer issues</span></li>
</ul>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">Requirements:</strong></p>
<ul class=" text-base sm:text-lg marker:text-color list-inside list-disc text-gray-500 list-disc list-outside pl-3 mb-6">
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">4+ years experience in technical support roles</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">1+ years experience with networking. You should know what a subnet is and what routing does. CCNA or equivalent is a plus. Extensive experience with Tailscale is even better</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Interpersonal communication skills and the ability to work effectively on a team</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Excellent written communication skills. Much of the role is via email and forum-based conversations</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">A strong desire to work with customers and partners in solving problems</span></li>
</ul>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">As a company, we strive to maintain fair and equitable compensation practices within our team across all roles and all levels. We use San Francisco market data to establish our pay ranges.</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">CAN Pay Ranges</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3">$129,980—$162,140 CAD</p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><em>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.</em> <strong class=" font-semibold"><em>We encourage you to help us break that statistic!</em></strong></p>
<p class=" text-gray-200 text-base sm:text-lg leading-relaxed mb-3"><strong class=" font-semibold">What We Offer</strong></p>
<ul class=" text-base sm:text-lg marker:text-color list-inside list-disc text-gray-500 list-disc list-outside pl-3 mb-6">
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200"><strong class=" font-semibold">An inclusive, flexible environment where you can be your authentic self.</strong> 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.</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200"><strong class=" font-semibold">A competitive total compensation package.</strong> This includes a base salary, an equity incentive plan and variable commission (for quota-based roles).</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200"><strong class=" font-semibold">Comprehensive group benefits with no waiting period.</strong> Take advantage of coverage for health, vision, dental, and more for you and your family!</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200"><strong class=" font-semibold">All-remote with the opportunity to work from anywhere</strong>—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).</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200"><strong class=" font-semibold">Connect with other Tailscalars IRL.</strong> 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.</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200"><strong class=" font-semibold">Support for your personal and professional development.</strong> Grow your career thoughtfully with $1500 USD annually for professional development, or take advantage of mentorship, coaching, and internal promotion opportunities.</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200"><strong class=" font-semibold">Paid time off and a healthy work-life integration.</strong> Our flexible, paid time off program supports you for any situation life throws your way, whether moving homes or travelling the world! We encourage all Tailscalars to take 4-6 weeks of vacation annually**.**</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200"><strong class=" font-semibold">A build-your-own home office setup.</strong> 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.</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200"><strong class=" font-semibold">Generous parental leave program from your first day.</strong> 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.</span></li>
</ul>