For Series A or B startups, if you have 5-10 yoe, what kind of upside are you looking for assuming you’re able to sell your equity by the time it vests in ~4 yrs? 500k, 1M, multiple MM?

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Maybe I'm missing something, but I'm not sure this can be answered generally. It depends how much equity you were given and what it's valued at (which depends how well the business does). At my last startup gig, I had the CFO give me a 30 min tutorial on equity. I came away with the sense it wasn't really worth anything until there was a 'liquidation event' (acquisition or IPO).

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Layoffs. Sheesh. Sounds like a terrible experience. No wonder they’re still Series A

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Series A/B start-up liquidity event should put you in the "next earning class" at least. The 5-10 YOE range is pretty vague and not sure what PO typically make, but I'd look at what your skip at a non start-up makes and declare that as a upside goal.

For series A/B probably at least 2M.

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