Employee options have a 10 year limit, and given the age of the company some employees were going to lose their options if they don't exercise. But to exercise you need to pay, in cash, the strike price plus taxes. I believe this founding round is to cover this.
> Because if Stripe let millions of dollars in compensation expire
I suppose they're still paying salaries, people will still want to work there. Maybe not the people who now only target the high comps provided by share options and related stuff, that's true.
ISOs may have a 10 year limit, but that's only for their ISO tax treatment status... they don't (necessarily) need to expire. They can convert to NSO by way of an extension. https://www.esofund.com/blog/nso-extension