Engineering Manager | 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">We’re seeking a talented and motivated full-time Software Engineering Manager to join our growing team. You will work as part of the engineering team to:</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">Provide guidance, mentorship, and career development for a team of software engineers.</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Contribute toward the success of our Product organization which includes Engineering, Product Management, and Design. We operate in Pods of 2-4 engineers plus a Product Manager and Designer, and each Engineering Manager handles 2-3 such Pods.<br />
<!-- -->Pods work across the codebase to implement features, address shortcomings, and answer customer requests.</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Provide technical direction in projects as needed, as well as growing the technical leadership capabilities of the engineers reporting to you.</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Help in growing the organization: interviewing and recruiting, guiding the development of the engineering culture, developing processes as we grow.</span></li>
</ul>
<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 help move the product forward. The ability to think on your feet, collaborate with highly technical teams, and comfort working asynchronously are essential.</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">Experience as a people manager: we are not yet at a size and level of maturity as an engineering org to provide the training and support for someone new in the management role.</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Achieve significant business outcomes through cross-functional collaboration with product managers, data scientists, and designers</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Help your team to improve their performance, the quality of their work; make major design decisions</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Hire, nurture, and oversee a team of engineers while fostering an atmosphere of psychological well-being, embracing diversity and promoting inclusion.</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Lead a team responsible for managing a critical production service, including operational concerns (monitoring, alerting, on call, etc)</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Manage healthy conflict by moderating design discussions and cultivating a positive culture of feedback with candor and kindness</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Collaborate with interdisciplinary teams across the organization to complete complex projects spanning multiple technical domains</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Drive planning across multiple time horizons, from immediate tactical needs to long-term strategic direction.</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">Demonstrated leadership with substantial experience in managing and mentoring Engineering teams, including performance evaluations, career development, and fostering a collaborative work environment</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Background in one or more of the skillsets used within Tailscale Engineering; management benefits from having the context to understand the work of the team. At this time, expertise in one of the following would be especially relevant:<!-- -->
<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">Networking including L4-L7 connectivity, browser and DNS behaviors, BGP and related protocols</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Data Engineering including Snowflake, dbt, Rudderstack, and similar tools</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Design and maintenance of distributed systems and highly available services</span></li>
</ul>
<p></span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Experience developing in Go, used for much of the system. Previous experience in #golang makes ramping up quicker</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Ability to give and process constructive feedback, as well as work independently</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Flexibility to adjust to the dynamic nature of a startup</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">$254,600—$344,380 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">We’re seeking a talented and motivated full-time Software Engineering Manager to join our growing team. You will work as part of the engineering team to:</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">Provide guidance, mentorship, and career development for a team of software engineers.</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Contribute toward the success of our Product organization which includes Engineering, Product Management, and Design. We operate in Pods of 2-4 engineers plus a Product Manager and Designer, and each Engineering Manager handles 2-3 such Pods.<br />
<!-- -->Pods work across the codebase to implement features, address shortcomings, and answer customer requests.</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Provide technical direction in projects as needed, as well as growing the technical leadership capabilities of the engineers reporting to you.</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Help in growing the organization: interviewing and recruiting, guiding the development of the engineering culture, developing processes as we grow.</span></li>
</ul>
<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 help move the product forward. The ability to think on your feet, collaborate with highly technical teams, and comfort working asynchronously are essential.</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">Experience as a people manager: we are not yet at a size and level of maturity as an engineering org to provide the training and support for someone new in the management role.</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Achieve significant business outcomes through cross-functional collaboration with product managers, data scientists, and designers</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Help your team to improve their performance, the quality of their work; make major design decisions</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Hire, nurture, and oversee a team of engineers while fostering an atmosphere of psychological well-being, embracing diversity and promoting inclusion.</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Lead a team responsible for managing a critical production service, including operational concerns (monitoring, alerting, on call, etc)</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Manage healthy conflict by moderating design discussions and cultivating a positive culture of feedback with candor and kindness</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Collaborate with interdisciplinary teams across the organization to complete complex projects spanning multiple technical domains</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Drive planning across multiple time horizons, from immediate tactical needs to long-term strategic direction.</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">Demonstrated leadership with substantial experience in managing and mentoring Engineering teams, including performance evaluations, career development, and fostering a collaborative work environment</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Background in one or more of the skillsets used within Tailscale Engineering; management benefits from having the context to understand the work of the team. At this time, expertise in one of the following would be especially relevant:<!-- -->
<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">Networking including L4-L7 connectivity, browser and DNS behaviors, BGP and related protocols</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Data Engineering including Snowflake, dbt, Rudderstack, and similar tools</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Design and maintenance of distributed systems and highly available services</span></li>
</ul>
<p></span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Experience developing in Go, used for much of the system. Previous experience in #golang makes ramping up quicker</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Ability to give and process constructive feedback, as well as work independently</span></li>
<li class=" leading-snug mb-2 pl-2"><span class="text-gray-200">Flexibility to adjust to the dynamic nature of a startup</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">$254,600—$344,380 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>