Director – Customer Support @ Tailscale

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

As the Director of Customer Support at Tailscale, you’ll be responsible for leading and developing our customer support team, ensuring exceptional service delivery, and driving customer satisfaction. You’ll work closely with cross-functional teams to improve our product and processes based on customer feedback.

What You’ll Do

Provide visionary leadership and mentor a team of technically skilled customer support professionals, fostering a culture of excellence, innovation, and continuous improvement
Develop and implement customer support strategies aligned with Tailscale’s goals and vision
Establish and monitor key performance indicators (KPIs) for the support team, leveraging data-driven insights to ensure high-quality service delivery now and into the future
Collaborate with Product, Engineering, and Revenue teams to address customer needs and enhance the overall customer experience
Lead in-depth analyses of customer feedback and support data to identify trends and opportunities for product and process improvements
Implement and optimize support tools and technologies to increase efficiency and effectiveness
Oversee the development and continual enhancement of support documentation, knowledge bases, and training materials
Manage the support team’s budget and resources effectively
Represent the voice of the customer within the organization, ensuring that customer needs and preferences are prioritized and addressed in strategic decision-making processes

You may be a fit for this role if you have:

7+ years of experience in customer support or related fields, with at least 3 years in a leadership role
Demonstrated experience supporting a broad range of customer types, from individual B2C users all the way to enterprise customers in the B2B SaaS space
A strong understanding of SaaS, networking, and security concepts
Familiarity with VPNs, networking protocols, and cybersecurity concepts
An eagerness to learn, keeping yourself and your team up with evolving customer questions and Tailscale’s product roadmap
Excellent communication and interpersonal skills, with the ability to interact effectively with both technical and non-technical stakeholders
A proven track record of building and scaling high-performing support teams
Experience with support tools and technologies (e.g., Jira Service Manager)
A data-driven approach to problem-solving and decision-making
Experience with remote team management (though expect to organize and participate in meetups with your team from time to time)

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.

CAN Pay Ranges

$239,860—$300,160 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!
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.

Compensation Overview

6 month growth

1 year growth

2 year growth

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