Lead and manage onboarding for new strategic customers, providing training and resources for long-term success
Provide technical support by diagnosing and resolving issues across Tailscale’s platform
Assist with configuration, integration, and troubleshooting for smooth implementation
Conduct quarterly business reviews covering usage, success metrics, and future goals
Identify opportunities for deeper customer engagement and horizontal expansion
Build customer relationships as a trusted advisor and recommend best practices based on use cases and business outcomes
Relay customer feedback and insights to product and engineering teams
Collaborate with sales, product, engineering, and support teams on handoffs, escalations, and customer success
Develop and maintain technical documentation, FAQs, and guides for customer self-service
Share insights and best practices with customers and internal teams
Requirements
6+ years in a technical role, including at least 2 years of customer-facing experience
Experience working with enterprise customers in a consultative capacity
Strong understanding of networking, VPNs, and security principles
Experience with cloud infrastructure such as AWS, GCP, and Azure
Experience with Docker, Kubernetes, and other DevOps technologies
Prior customer-facing technical experience as a Technical Support Engineer, Solutions Engineer/Architect, or Customer Success Engineer at a SaaS company
Ability to explain complex technical concepts to diverse audiences
Strong written and verbal communication skills
Analytical mindset and troubleshooting skills for complex technical issues
Ability to manage multiple customer accounts, prioritize tasks, and keep projects on track
Strong time management and organizational skills
Ability to work cross-functionally with product, sales, and engineering teams
Benefits
An inclusive, flexible environment where you can be your authentic self
Competitive total compensation package including base salary, equity incentive plan, and variable commission for quota-based roles
Comprehensive group benefits with no waiting period, including health, vision, and dental coverage for you and your family
Remote-first work environment
Virtual and in-person social events
Corporate co-working program
Employer-funded retirement contributions matching contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of eligible compensation
Annual company retreat and team off-sites
$1500 USD annually for professional development
Mentorship, coaching, and internal promotion opportunities
Flexible paid time off program
Company-owned laptop (Mac or PC)
Monthly home internet reimbursement
$500 USD workstation customization allowance
Paid parental leave top-ups: 20 weeks for birthing parents and 16 weeks for non-birthing parents
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