Raising today 100M you'd want to at least, worst case, triple the exit valuation, and so you grow as crazy your enterprise sales for the next year or two so your 15x ARR gets to $3-4B and you sell for $6B+ and let the buyer carry all that support and tech debt.
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Raising today 100M you'd want to at least, worst case, triple the exit valuation, and so you grow as crazy your enterprise sales for the next year or two so your 15x ARR gets to $3-4B and you sell for $6B+ and let the buyer carry all that support and tech debt.