Implementation Engineer
Tailscale - Remote (Canada)
Posted Feb 23, 2026
Benefits
- Parental leave
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- Non-birth-parent leave
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- Family-building benefits
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- Fertility benefits: Not verified
- Adoption assistance: Not verified
- Surrogacy assistance: Not verified
- Mental health support
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- Relocation assistance
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- Childcare support
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- Learning budget
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Schedule
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- Weekend work
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Where they hire
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About this role
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
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