Implementation Engineer, Tailscale
CA$143.4-170.2k
OTE
+ Equity + variable commission
More information about location
A zero config VPN for building secure networks
Be an early applicant
A zero config VPN for building secure networks
201-500 employees
Be an early applicant
CA$143.4-170.2k
OTE
+ Equity + variable commission
More information about location
201-500 employees
Company mission
To remove overhead and complexity from the “long tail” of software and operational problems that people face every day.
Role
Who you are
- 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
- 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 the job involves
- 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
- 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
Our take
The internet is a global phenomenon, but often online activity is unprotected which leaves users vulnerable to hackers on public networks. Additionally certain sites are inaccessible or censored depending on the users location. Use of a VPN enables a secure connection through an encrypted virtual tunnel which also disguises IP addresses. Traditional VPN's tunnel all network traffic through a central gateway server which can affect reliability, and VPN's almost always slow connection speed.
Tailscale is a VPN service built on top of a secure network fabric, which is unlike a traditional VPN provider as it ensures encrypted point-to-point connections by using the open source WireGuard protocol. Tailscale is configured, on average, in a matter of minutes, while other solutions take weeks to fully implement and then require several hours a week of maintenance.
The product has been well received, with reviewers agreeing that it is easy to set up and a great tool for developers. The company plans to develop its product further by tackling the complexity of software and confronting operational problems that people face daily. Off the back of impressive 2025 funding, Tailscale is expanding its engineering, product and sales teams as well as its global reach, all to empower small teams to build systems that scale, without scaling overhead.
Steph
Company Specialist at Welcome to the Jungle
Insights
81% employee growth in 12 months
Company
Funding (last 2 of 4 rounds)
Apr 2025
$160m
SERIES C
May 2022
$100m
SERIES B
Total funding: $275m
Company benefits
- Flexible (and reasonable) working hours—work/life balance is exceptionally important to us
- Competitive compensation, stock options and 401(k) (for United States-based employees)
- Comprehensive medical/dental/vision benefits, and more
- 4 weeks of paid vacation (standard across the company) + 12 company holidays per year
- An allowance for equipment to help you personalize your workspace
Company HQ
King West Village, Toronto, ON
Leadership
Avery Pennarun
(Co-Founder & CEO)A range of experience in software engineering including Senior Staff Software Engineer at Google Fiber. They co-founded EQL Data in 2009.
David Crawshaw
(Co-Founder & CTO)Previous experience includes working as a Staff Software Engineer at Google before co-founding Tailscale.
David Carney
(Co-Founder)Co-founded Format in 2012, working as a Full Stack Developer, COO and CFO. Also co-founded Form & Method and The Navarra Group.
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