Reddit reviews Mastering the VC Game: A Venture Capital Insider Reveals How to Get from Start-up to IPO on Your Terms

i'm not quite a CFO but i do work in tech / at a startup / in finance. i can give a quick list of stuff I'd recommend to someone making the jump:

• Kind of a no brainer (and judging from your analysis on #1, this probably won't be an issue) but you should be familiar with the VC/ funding/legal side of things. You can be the most valuable person in the room if you like slicing through a term sheet. i'd recommend Brad Feld's Venture Deals to get your feet wet. From a more macro/ company building level, Bussgangs Mastering the VC Game is a nice, light read.
  
  
• Again, probably why they're hiring you, but strong financial modeling skills are important. Being able to do the historical accounting/ cash analysis and then quickly turn that into a forecast grounded in some business logic is essential. You're going to be making shit up sometimes, but I think everyone is to some degree in early stage tech.
  
  
• I'm not sure the size of this company, but it's probably small and you'll probably end up dealing with/managing a lot of unsexy stuff. Running payroll, administering benefits, getting a 401k set up is all very painful but part of building yourself into a real company that can hire top notch talent. of course you can hire some/most of this stuff out, but it will probably be your problem at the end of day.
  
  
• again, not sure what kind of team you're leading, but dealing with the accounting side. judging on the 2 year timeline, you'll probably be due for your first Audit and have to lead a few 409a valuations. deal with taxes/whatever else comes up.
  
  i think great CFOs for early stage can run the finance side but also kick in with the Ops stuff and have a good handle on product. You're more of the grease, and your job is to keep things humming and get out of the way to let people build.

Venture Deals is great and I'd also strongly recommend Mastering the VC Game by Jeff Bussgang. It's a really easy read and brings a lot of clarity to the subject of equity financing.

Amazon link