Forward Deployed Engineer

Tailscale

$150K — $250K *
US-AnywhereRemote in United States
Technical Services
5 - 7 years of experience
Job Overview by Ladders

Qualifications

  • 6+ years in a technical role with minimum 2 years of customer-facing experience.
  • Experience with enterprise customers in a consultative capacity.
  • Strong understanding of networking, VPNs, security principles and cloud infrastructure (AWS, GCP, Azure).
  • Prior experience in a customer-facing technical role at a SaaS company, such as Technical Support Engineer or Customer Success Engineer.
  • Ability to explain complex technical concepts to both technical and non-technical audiences.
  • Analytical mindset and troubleshooting skills for technical issue resolution.
  • Passion for customer service and building long-term relationships.
  • Strong organization and time-management skills for handling multiple accounts.

Responsibilities

  • Lead onboarding for new strategic customers to ensure rapid adoption of Tailscale.
  • Provide technical support by diagnosing and resolving issues within the platform.
  • Conduct QBRs with clients to review usage and identify deeper engagement opportunities.
  • Build strong customer relationships, providing tailored recommendations for best practices.
  • Act as the voice of the customer to relay feedback to product and engineering teams.
  • Collaborate with sales and support teams to ensure seamless handoffs and escalation of issues.
  • Develop technical documentation to facilitate customer self-service and share best practices.

Benefits

  • Inclusive and flexible work environment that values diverse voices and backgrounds.
  • Competitive total compensation package including equity incentives.
  • Comprehensive group benefits with immediate coverage for health, dental, and vision.
  • Remote-first company culture with options for co-working space.
  • Employer-funded retirement contributions matched up to 0.75% of eligible compensation.
  • Opportunities for personal and professional development with an annual budget for training.
  • Flexible paid time off program for work-life integration.
  • Funding for home office setup to tailor your workspace to your needs.
  • Paid parental leave program with top-ups for new parents.
Full Job Description
About the Role

As a Forward Deployed Engineer 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

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.

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

US Pay Range (OTE)

$150,000-$250,000 USD

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!
  • Remote first company-most of our teams work fully remotely. 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). Some roles require in-office collaboration depending on team needs, which will be clearly noted in the job description.
  • Employer-funded retirement contributions. Tailscale will match your retirement contributions dollar-for-dollar, up to a maximum annual employer contribution equal to 0.75% of your eligible compensation.
  • Connect with other Tailscalars IRL. Attend our annual company retreat, participate in team off-sites, and collaborate in person with teammates across Canada, the United States, the United Kingdom, and Singapore. We support intentional in-person connection through team travel and distributed collaboration.
  • 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!
  • A build-your-own home office setup. You choose your own company-owned laptop (Mac or PC), receive a monthly home internet reimbursement, and $500 USD to customize your workstation to make it your own.
  • Paid parental leave program. We care about your life outside of work and encourage new parents to take advantage of parental leave top-ups (20 weeks for birthing parents, 16 weeks for non-birthing parents).

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