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Job Description

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 are seeking a customer-centric and empathetic Manager of Customer Support to lead an amazing team of support engineers dedicated to ensuring all of our users have an amazing experience with Tailscale. The ideal candidate will have a background in supporting users of a technical SaaS product (security a plus!), an analytical mindset, and experience in managing teams in a fast-paced, customer-centric environment. As a key leader in the Customer Support organization, you will collaborate closely with Engineering, Product, Marketing, and Sales teams to resolve complex technical issues, drive continuous improvement, and contribute to customer retention and satisfaction. The role will report directly to the VP of Customer Experience.

Key Responsibilities

• Manage, mentor, and develop a team of Customer Support Engineers, ensuring effective prioritization, resolution of technical issues, and continuous skill development.
• Oversee the resolution of complex customer support tickets, ensuring timely and accurate responses to technical inquiries related to our SaaS security products.
• Collaborate with support operations to identify and implement process improvements to streamline customer support workflows, enhance productivity, and improve customer satisfaction.
• Collaborate with the technical writer team to ensure the development and maintenance of an up-to-date knowledge base, FAQs, and troubleshooting guides. 
• Collect customer feedback and work closely with the product and engineering teams to identify potential product improvements and to prioritize customer needs.
• Monitor team performance through KPIs and SLA adherence, ensuring the team meets targets for response times, resolution times, and CSAT.
• Develop and deliver training programs for new hires and ongoing education for the customer support team.
• Evaluate and implement new tools and technologies that enhance the support team’s efficiency, including automation through AI, ticketing systems, and new ways of engaging customers.

What We Are Looking For

• 7+ years of experience in customer support or customer success engineering, with at least 3-5+ years in a leadership or people manager role.  
• Experience working with SaaS products or in a security-focused technical environment is highly preferred.  
• Strong understanding of Cloud Service Provider landscape, networking concepts, and security frameworks.
• Expertise in troubleshooting technical issues related to cloud infrastructure, security, and network configurations.  
• Comfort in working with SaaS tooling and leveraging data to highlight key areas of improvement/investment
• Strong written and verbal communication skills, with the ability to clearly explain complex technical concepts to non-technical customers.  
• Experience in crafting and collaborating on technical documentation, knowledge bases, or troubleshooting guides.
• Proven ability to lead, motivate, and grow a high-performing team in a fast-paced environment
• Excellent analytical and problem-solving skills, with the ability to think critically and diagnose issues in a timely manner.

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.

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!
• All-remote with the opportunity to work from anywhere—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). 
• 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! We encourage all Tailscalars to take 4-6 weeks of vacation annually. 
• 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.