Hey there! Brian from Levels.fyi here, wanted to jump in and respond. I think both offers are great, but if you calculate out the totals a bit, I think offer 2 definitely seems like the better choice. I plugged all your numbers into our offer calculator so you can take a peek at what the total numbers look like. https://www.levels.fyi/calculator/?co=A&bs=200000&sgt=total-stock-grant&sbone=20000&bp=13&co-2=B&bs-2=160000&sg-2=265000&sgt-2=total-stock-grant&sbone-2=10000 Keep in mind that I did not add any 401k matches to these, nor did I add offer 2's performance bonus (because I didn't know how much it was), but even then, you can see the numbers are super similar, with Offer 1 having a bit more in that first year due to the higher signing bonus. But, like you said as you consider your benefits, option 2 seems like the better choice long term, plus calculating in the performance bonus means that their comp is actually probably over offer 1 in totality. If you want help negotiating either of these offers, I'd definitely recommend checking out our negotiation coaching service! We can help you negotiate them a bit more to ensure you're not leaving anything on the table. I also offer a free consultation, so if you'd like to chat more, let me know! You can find our coach booking and consultation booking here: https://www.levels.fyi/services/