Solo sysadmin with 6 months experience at an SMB (~500 staff) being asked to get entire org SOC2 compliant. Zero experience with compliance. Is this reasonable?

Oh fuck no that’s not reasonable. I have well more than 20 years of IT experience and I’m about to do this nearly solo at a much smaller org. I’m also fairly well-versed in compliance, and I can barely handle it¹. It’s a huge task, with hundreds of interlocking parts necessitating deep understanding not just of IT but of the entire business and of various compliance requirements.

Someone with only six months of sysadmin experience going for SOC 2 is like sending out a gaggle of kittens to fight a rhinoceros. It’s just not gonna happen.

When I was working at a company of similar size to the OP’s, it took a team of about a dozen people working on it nearly full-time for 18 months to get SOC 2 Type II. I’d expect about the same anywhere.

1. And I also have the advantage of expertise in more areas than the average IT person.