Implementation Engineer

Remote (Canada)

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 an Implementation Engineer (IE) at Tailscale, you are the primary architect of a customers’ first experience with our product. Reporting to the CSE Team Lead, you will sit at the intersection of Pre-sales, Support, and Product with the mission of value attainment for our customers. You will manage a high volume of accounts across commercial and enterprise segments, guiding them through the critical first 30 days of their journey. This is a high-impact, technical role designed for someone with intellectual curiosity, empathy, strong networking fundamentals, and a passion for helping customers solve complex connectivity/security challenges with Tailscale. You will ensure that Tailscale becomes a foundational part of our customers’ infrastructure from day one.

Key Responsibilities

  • Own the end-to-end technical onboarding journey for a high volume of accounts, with a relentless focus on ensuring customers reach Time To Value (TTV) in under 30 days.
  • Provide hands-on guidance for technical configurations, including Identity Provider (IdP) integration, Tailnet administration, ACL policy definition, and MDM deployments.
  • Partner closely with AEs and SEs to ingest technical requirements from the pre-sales cycle and ensure a seamless transition to active usage.
  • Act as a critical feedback loop for the Product and Engineering teams by identifying recurring friction points or bugs during the onboarding phase and advocating for fixes.
  • Maintain rigorous data hygiene within sales (SFDC) and CSP tooling to provide visibility into onboarding completion rates, TTV, and overall customer health metrics.
  • Bridge the gap between initial setup and long-term support by facilitating clean handoffs to the Support and Post-sales teams once adoption milestones are met.
  • Define and refine onboarding success metrics, including the development of post-onboarding surveys and in-product adoption targets.

What We Are Looking For

  • 2–4+ years of experience in a technical, customer-facing role such as Technical Support, Implementation, or Solutions Engineering
  • Strong foundational knowledge of networking concepts including the OSI model, DNS, routing, and VPN operations (experience with Tailscale preferred)
  • Proficiency in installing software across diverse operating systems, including Linux, Windows, macOS, and iOS/Android (experience with Mobile Device Management is a plus)
  • Strong skills in diagnosing, troubleshooting, and resolving issues related to networking
  • Ability to read and modify JSON or YAML configs for ACL and Kubernetes deployments
  • Exceptional organizational skills with a proven ability to manage a high volume of concurrent tasks across multiple revenue segments without compromising quality
  • Clear and empathetic communication style, with the ability to translate complex networking concepts into actionable steps for technical and non-technical stakeholders alike
  • A builder’s mindset, meaning you enjoy solving technical puzzles and are motivated by seeing a customer successfully deploy a solution you helped architect

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)

$143,380 - $170,180 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!
  • 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.
  • 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, and the United Kingdom. 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 $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. 

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.

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