Forward Deployed Engineer

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About Tailscale

Tailscale is making safe connection effortless 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.

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 the Team Lead, Customer Success Engineers.

Key Responsibilities

Design and build novel solutions to complex customer challenges that fall outside Tailscale’s standard deployment patterns (e.g., prototyping custom integrations, tooling, and network architecture; using structured experimentation and testing to validate solutions for bespoke client uses)

Turn one-off customer solutions into repeatable, reusable assets such as reference architectures, deployment frameworks, and tooling, that can be applied across the broader customer base.

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.

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

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).

Tailscale is committed to providing an accessible and inclusive hiring process. If you require an accommodation at any stage of the recruitment process or related to any aspect of this role, please contact your recruiter.

Our hiring process uses AI-assisted tools to help screen and assess candidates. All hiring decisions are made by people.

Please be aware that legitimate emails from Tailscale's talent team will only originate from @tailscale.com, @greenhouse.io, and @interviews.modernloop.io email addresses. For more information about protecting yourself from impersonators and scams, please visit https://tailscale.com/scam-awareness.