Episode 276: Startup or big company and negotiating your exit?

In this episode, Dave and Jamison answer these questions:

Questions

Hi guys, I’ve been listening for a few months now and am dissatisfied with my current work, where I’ve been for a year. I come from a research background, and now doing an engineering job at a B2B SaaS company is leaving me wanting a change. Moving between teams is not an option, so I plan to move companies early next year. My problem is that I don’t know whether to look for another large or mid-size company (I’m finishing final rounds at Facebook and Palantir), or go to a startup where it is likely to be more interesting (I have an offer to be the lead engineer at a very small startup, where there are already 5 developers). I have one year of industry experience. If I go to the startup, will it negatively impact my career in the future if/when I want to move elsewhere? Would it be easier to move elsewhere, and get a better offer or a higher position, if I work at Facebook or Palantir instead of this startup? Also, while I prefer research, I’m not in the position to go back to grad school and finish my PhD (I finished my MS and left to work) for monetary reasons, so I need to move to another engineering position.
I’ve often heard of senior employees “negotiating their exit” instead of resigning/quitting, with rumors of large negotiated payouts. I assume that’s just a select group of people who can, but I’ve never seen much written on that. What is the situation where you can do this? How do you set yourself up for being able to get a payout like this?