How do I judge a startup's GTM before I join it, so I am not walking into an unhittable number?
Interview them harder than they interview you, and ask for numbers rather than stories. The four that matter most: what percentage of the team hit quota last year (under half is a warning, sixty to seventy is healthy, over eighty usually means the number goes up next year), why the person in this seat left, what share of closed revenue came from inbound versus self sourced, and how long a new rep takes to ramp. Then look at whether the motion exists at all: is there a demand generation function, does anyone have a written playbook, is there sales engineering support, is the buyer consistent across recent wins. Also check the boring financial facts, runway and the next raise, because a great territory in a company that runs out of money is not a great territory. If they will not share attainment data, that is your answer.
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This is the diligence checklist itself, grouped into territory health, product market fit, financial health, leadership and marketing support, with the exact questions to say out loud. The territory questions (why did the last rep leave, what were attainment and net new numbers) are the ones candidates are most afraid to ask and most need to.
Shorter and blunter than a full diligence list, and it focuses on the comp plan itself: how pay is actually calculated and what realistic attainment looks like, which is where most bad offers hide. Good as the version you can read on the way to the interview.
Drawn from 170 plus B2B SaaS companies, so when a startup quotes you a quota and an OTE you can check both against a median (800K annual quota, 190K OTE at roughly a 53:47 split). Numbers far off the median are not automatically wrong, but they are a question you should ask before you sign.
