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I had a very easy time selling this. We moved away from an OpenVPN setup, and Tailscale made it so much easier to onboard new employees and to do a lot more thi

I had a very easy time selling this. We moved away from an OpenVPN setup, and Tailscale made it so much easier to onboard new employees and to do a lot more things “the right way”. We’re a fully remote company, so it’s even more important. Although I admit that in my role I have quite a lot of weight in convincing management on these topics, price was not a concern. We’ve been a happy customer since April last year, everyone on the premium / “expensive” tier. I’m also very impressed with their development speed: some features that were said “May take a few years to be delivered” actually were delivered last year already. Cloudflare One could have been an alternative, but that would have been even more expensive.

snapplebobapple 3y ago
Yah, if I was a fully remote company this would have been an easier sell. What I actually am (and what the vast majority of business likely is) is a small bunch of office locations and a bunch of cloud infrastructure so I can approximate tailscale in a way I am unhappy with right now by limiting cloud access to the ips of the office and controlling access with various things from the office pcs. The vpn to do that works properly with acls and is included in our networking gear. So what tailscale is competing with is something that is a sunk cost and not ideal but of minimal additional cost vs 20k a year of additional cost providing premium features to all users when maybe 10% of users need them. Basically, tailscale has a bundling problem. They bundled necessary to all features (proper acls) with a bunch of premium stuff that is of less value to many and they don't have the market power of microsoft with their windows operating system to force that kind of arrangement down my throat. They need a 2-3 dollar a month tier with proper acls and mesh vpn, then al a carte of the rest of the feature bloat per user (ssh key management is worth no more than 2 dollars a month based on the competition, no idea what the other features are worth because I have no use for them). They also really need to improve their windows experience. More than once during testing I had a windows update break the vpn requiring alternate means of logging in and reconnecting, but that's an ancillary issue.

snapplebobapple 3y ago

Yah, if I was a fully remote company this would have been an easier sell. What I actually am (and what the vast majority of business likely is) is a small bunch of office locations and a bunch of cloud infrastructure so I can approximate tailscale in a way I am unhappy with right now by limiting cloud access to the ips of the office and controlling access with various things from the office pcs. The vpn to do that works properly with acls and is included in our networking gear. So what tailscale is competing with is something that is a sunk cost and not ideal but of minimal additional cost vs 20k a year of additional cost providing premium features to all users when maybe 10% of users need them. Basically, tailscale has a bundling problem. They bundled necessary to all features (proper acls) with a bunch of premium stuff that is of less value to many and they don't have the market power of microsoft with their windows operating system to force that kind of arrangement down my throat. They need a 2-3 dollar a month tier with proper acls and mesh vpn, then al a carte of the rest of the feature bloat per user (ssh key management is worth no more than 2 dollars a month based on the competition, no idea what the other features are worth because I have no use for them). They also really need to improve their windows experience. More than once during testing I had a windows update break the vpn requiring alternate means of logging in and reconnecting, but that's an ancillary issue.