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 Customer Success Engineer (CSE) at Tailscale, you’ll be the bridge between our technical capabilities and the needs of our most strategic customers.

You will work directly with customers to ensure their success with Tailscale’s products, helping them get onboarded, driving their long-term adoption, and providing expert technical guidance throughout their journey.

This role requires a combination of technical proficiency, problem-solving skills, and an empathetic customer-centric approach to ensure customers are fully empowered to leverage the power of Tailscale.

The role will report directly to Zach Buchheit, Team Lead, Customer Success Engineers.

Key Responsibilities

Lead and manage the onboarding process for new strategic customers, ensuring they quickly understand and adopt Tailscale. Provide training and resources that set customers up for long-term success
Offer technical support for customers, diagnosing and resolving issues across Tailscale's platform. Assist with configuration, integration, and troubleshooting to ensure smooth implementation
Conduct QBRs with customers to review usage, success metrics, and future goals. Use these touchpoints to identify opportunities for deeper engagement and horizontal expansion
Build strong relationships with customers, acting as a trusted advisor. Help customers optimize their use of Tailscale by identifying best practices, and by providing recommendations based on their specific use cases and desired business outcomes
Serve as the voice of the customer internally, relaying feedback and insights to the product and engineering teams to help improve the product and the customer experience
Work closely with sales, product, engineering, and support teams to ensure smooth handoffs, escalate critical issues, and drive customer success across the organization
Develop and maintain a repository of technical documentation, FAQs, and guides to help customers self-serve. Share insights and best practices with both the customer and internal teams

What We Are Looking For

6+ Years in a technical role with minimum 2 years of customer-facing experience (Solutions engineer/architect, Sr. Support Engineer, etc.)
Experience working with enterprise customers in a consultative capacity
Strong understanding of networking, VPNs, and security principles. Experience with cloud infrastructure (AWS, GCP, Azure) and tools like Docker, Kubernetes, and other DevOps technologies
Prior experience in a customer-facing technical role such as Technical Support Engineer, Solutions Engineer/architect, or Customer Success Engineer at a SaaS company
Ability to clearly explain complex technical concepts to a diverse audience, from non-technical stakeholders to engineers. Strong written and verbal communication skills are a must
Analytical mindset and troubleshooting skills, with the ability to think critically and methodically to resolve complex technical issues
A passion for delivering excellent customer service and a strong focus on building long-term customer relationships
Ability to manage multiple customer accounts, prioritize tasks, and keep projects on track. Strong time management and organizational skills are key
A collaborative mindset and ability to work cross-functionally with product, sales, and engineering teams to deliver customer success

Compensation

Tailscale's compensation package includes base salary, equity, and comprehensive benefits.

For this position, pay ranges reflect target OTE (on target earnings), inclusive of base salary and variable compensation tied to the attainment of quarterly sales targets.

CAN Pay Range (OTE): $201,000 - $335,000 CAD

What We Offer

An inclusive, flexible environment where you can be your authentic self
A competitive total compensation package (base salary, equity incentive plan, and variable commission for quota-based roles)
Comprehensive group benefits with no waiting period (health, vision, dental, and more for you and your family)
Remote-first company — most of our teams work fully remotely, with options for co-working spaces and intentional in-person collaboration
Opportunities to connect IRL: annual company retreat, team off-sites, and distributed collaboration across Canada, the U.S., and the U.K.
Support for personal and professional development ($1500 USD annually for professional growth, mentorship, coaching, and promotion opportunities)
Flexible paid time off program for any situation life throws your way
Build-your-own home office setup: choose your laptop, monthly internet reimbursement, and $1000 USD to customize your workstation
Generous parental leave program from your first day (top-ups for up to 26 weeks)
Commitment to accessible and inclusive hiring processes — accommodations available at any stage of recruitment

Customer Success Engineer