I don't think 4-5 years experience is Sr level, as used in the Robin example. $100k with 1% of the company seems... OK? The salary is a mid level software engineer is closer to $150k, Chicago should down adjust a bit, so maybe $130k salary in big tech. Realistically, you are looking at $162.5k with bonuses and stock. How much is the startup worth now? She's probably passed on (very roughly) $300k of comp, so if that startup valuation is sitting above $30M she might be close to even and if it provides an exit above $100M she'll have done well. If not, well it was a lottery ticket.
As for the other person, Staff+ does not necessarily translate between companies, and especially does not translate from companies in very different cultures to the big tech space. It's not impossible, but just because someone got the title of Staff engineer in one market does not mean they will be able to get that title in another market.
As for the other person, Staff+ does not necessarily translate between companies, and especially does not translate from companies in very different cultures to the big tech space. It's not impossible, but just because someone got the title of Staff engineer in one market does not mean they will be able to get that title in another market.