went through the full AE loop at OpenAI enterprise sales earlier this year. wanted to write this up because there's basically nothing out there.
five rounds total. roughly:
recruiter screen (30 min): standard background. they asked about my biggest deal size and whether i've sold into large enterprises vs. mid-market. they are building an enterprise motion, not a PLG one, so they want people who've actually navigated multi-stakeholder deals, legal back-and-forth, long cycles.
hiring manager screen (45 min): deeper dive on a specific deal from my history. they literally walked me through it like a case study. what was the org chart, who was the blocker, how did i get internal consensus, what was the competitive alternative the prospect considered. have a real story ready with specific numbers.
panel: two AEs + a sales ops person (60 min): this was the most substantive round. basically a panel doing a mutual evaluation. questions were about discovery methodology (they mentioned MEDDPICC but didn't require you to parrot the acronym), how i handle stalls, and how i think about pipeline coverage ratio. one of the AEs asked what i do when the champion loses their job 3 weeks before close. have an answer.
live mock pitch (45 min): they gave me a fictional prospect scenario. i had to do a discovery call cold. they played two personas. this is where people apparently wash out. they're not looking for a polished demo script, they're looking for whether you actually listen and pivot based on what the prospect says.
values/culture fit (30 min): with someone from people ops. lighter, but they do probe on why OpenAI specifically.
overall the process felt serious and calibrated. they're not doing this casually. the comp i was quoted was ~$150k base with a variable target bringing it close to $300k OTE, plus equity. no specific numbers guaranteed but ballpark was in that zip code.
if you're applying: know your deal history cold, have a strong point of view on enterprise AI adoption, and don't fake familiarity with their products because they will probe.