Pros
Supportive culture: Tailscale is the kind of place where everyone’s ideas are heard. Collaboration is natural, and the team is genuinely excited to solve tough problems together. Innovative work: It’s inspiring to work on a product that simplifies complex networking in such a clean, approachable way. You feel like you’re contributing to something that really matters. Flexibility: The remote-friendly setup and respect for work-life balance are huge perks. It’s great to work somewhere that understands life happens outside of work. Strong leadership: The leadership team is transparent and approachable. They’re genuinely invested in making Tailscale a place where people can thrive. Aligned values: The company’s focus on privacy, security, and open source is something I’m proud to stand behind—it feels good knowing the work we do has a real ethical foundation.
Cons
Like any growing company, there’s still some figuring out to do as processes evolve. But the team’s adaptability and willingness to improve make it feel manageable.
