For teams who want secure, private networks without weeks of setup and configuration, Tailscale makes it easy. Unlike existing corporate VPNs, Tailscale has no upfront cost, minimal latency, and works with their existing services.
Rating Reviews
Rating is calculated based on
18
reviews and is evolving.
Pros: I've really enjoyed the culture at Tailscale. As a Senior New Business Account Executive, I've seen firsthand how supportive the leadership is; they trust us to manage our pipelines and truly value input. The work flexibility is fantastic for someone in Denver, CO, with a remote-first setup that actually works, unlike some other tech companies. The collaboration within the sales team and with engineering is strong, fostering a great learning environment in the networking and cybersecurity
Cons: While career growth paths for a Senior New Business Account Executive are clear, the process for internal promotions can sometimes feel a little opaque or lengthy. During peak sales cycles, the workload can get pretty intense, requiring careful personal management to maintain a good work-life balance. Also, sometimes cross-functional communication on certain product roadmap changes could be more streamlined, especially in a fully remote environment, to help us better position solutions to
Advice to Management: Continue to invest in leadership training for middle management to enhance communication consistency. Streamline the internal promotion criteria for sales roles like Senior New Business Account Executive to provide more transparency. Exploring ways to reduce reliance on synchronous meetings would
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Pros: The biggest pro is the genuine remote-first culture and the work flexibility it provides. Tailscale has built a fantastic engineering team where everyone is exceptionally bright and collaborative. It's refreshing to work with colleagues who are so dedicated to the product and its mission of simplifying secure networking. The technical challenges are stimulating, and there's a lot of autonomy in how you approach your work. Leadership is transparent, and the company values a healthy work-life
Cons: While overall excellent, like any fast-growing tech company, there can be occasional communication overhead in a fully distributed environment, especially when bridging different time zones within Canada and internationally. Sometimes, the sheer pace of innovation means priorities can shift quickly, which is exciting but can also require rapid adaptation. Ensuring everyone is always perfectly aligned on the latest changes across all remote teams takes continuous effort. These are minor points,
Advice to Management: Continue fostering transparency and open communication. Invest in tools and practices that enhance asynchronous collaboration for remote teams across different regions.
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Pros: The biggest draw is the commitment to being a remote-first company. You get incredible work flexibility, and the focus on developer experience and tools is top-notch. It's refreshing to work on a product that's well-loved and solves real problems in network security and connectivity. Collaboration is efficient, and the team is genuinely smart and supportive. The pace feels productive without being overwhelming, which is rare.
Cons: As the company grows, some processes are naturally starting to show strain. Onboarding could be more structured, and cross-team communication, while good, sometimes needs clearer ownership. I've also noticed that career development paths, while present, could be more explicitly defined for individual contributors.
Advice to Management: Continue investing in robust onboarding and clearer paths for individual contributor growth. Standardizing some operational processes will help manage scaling effectively while maintaining the current high level of trust and flexibility.
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How long does Tailscale typically take to respond after applying for a remote engineering role?
After applying for a remote engineering role at Tailscale, I heard back about an initial screening call within about a week, which seemed pretty standard for a growing tech company.
Do I need to wear any special safety equipment when working remotely with Tailscale?
No, for remote work with Tailscale, no special safety equipment is needed beyond your standard computer setup. It's designed for secure access without physical gear, which is great for our distributed tech team.
What's the dress code like for remote meetings at Tailscale?
Since Tailscale is a remote-first company, dress code for virtual meetings is very relaxed; I usually wear a t-shirt or a casual button-down, just like most engineers and folks in product roles I interact with.
What's category management like at Tailscale for accountability?
In category management at Tailscale, accountability is built into the process; we own our product categories end-to-end, driving strategy and execution with clear ownership.
What was your experience like onboarding with Tailscale, especially regarding security and remote setup?
Onboarding at Tailscale was surprisingly smooth; they emphasize a secure, zero-trust model from day one, making remote collaboration easy for engineering roles, even in a growing startup.
How does Tailscale help with change management in a large tech company regarding network access?
In my experience at a mid-sized SaaS company, Tailscale simplified our change management by providing secure, consistent network access to all our engineers, regardless of their location, making rollouts much smoother.
How does Tailscale impact the daily workflow for remote software engineers?
Tailscale makes accessing internal dev environments and services seamless, significantly improving my productivity as a remote software engineer, regardless of my location. It feels like I'm on the office network, even when working from home.
What's it like working at a remote-first tech company like Tailscale, especially for software engineers?
As a software engineer at Tailscale, the remote-first culture is fantastic; I love the flexibility of working from anywhere, and the collaboration tools make connecting with my colleagues across different time zones seamless for our global team.
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