Tailscale

tailscale.comCybersecurityCanada51-200 employeesFounded 2019

About

Tailscale is a remote-first company building a zero-config VPN based on WireGuard for secure networks.

Reviews (5)

3.4 average

Interview experience

Proceed with caution — 50% reported a negative interview.

Positive (1)Neutral (1)Negative (2)

What people like

“low-ego team, stock that's actually worth something”
“genuinely smart coworkers, good 401k match”
“good 401k match, genuinely smart coworkers”

What to watch for

“slow promotions, internal politics”
“reorgs constantly”
“unclear expectations, bureaucratic, limited upward mobility”

Solid company, good people

Remote setup is dialed in — never once felt out of the loop. On-call was brutal and they didn't comp it at all.

Pros

low-ego team, stock that's actually worth something

Interview experience: Neutral

Keiko Haddad

16 days ago

Full-time

Glad I joined

tbh Best onboarding I've had. Had real context by the end of week one. Best onboarding I've had. Had real context by the end of week one.

Pros

genuinely smart coworkers, good 401k match

lena.adebayo

3 months ago

Full-time

Would not recommend

Overall, Burned out within a year, and I wasn't the only one.

Pros

good 401k match, genuinely smart coworkers

Cons

slow promotions, internal politics

Interview experience: Negative

Ruby Reyes

4 months ago

Full-time

Best job I've had so far

overall, PTO is respected, nobody guilt-trips you for taking it. Benefits are top tier, the parental leave alone is worth it.

Cons

reorgs constantly

Interview experience: Negative

Gabe Mueller

over 1 year ago

Full-time

Lots of red flags

Layoffs every other quarter — you're always watching your back. They preach work-life balance then ping you at 11pm.

Pros

supportive manager, great health benefits

Cons

unclear expectations, bureaucratic, limited upward mobility

Interview experience: Positive

Noah

almost 2 years ago

Full-time

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