$400k OTE Ent AE Series A or $300k + Equity Director at funded Seed
First off I know I am lucky to have both options on the table so want to get that out of the way. Trying to think this through and would love takes from people who’ve made this call.
For context, I’ve got 15+ years in high level sales mostly in early stage companies and I’m honestly a bit burnt out on being the Nth seller taking direction. The startup scratches the “run the show” itch and gets me a title I used to not want (I used to always prefer IC) but at my age thinking might be a better play.
Two roles on the table.
Option 1, Series A Company. $200K base, $200K variable, structured comp plan, real product market fit, but I’d be one seller of several running names accounts. Standard IC seat on a small-ish team. There is lore of 7 figure sellers from last year but thinking with the hiring plan that won’t be the case anymore. New vertical for me but it has been for most sellers, I think I have a strong chance to exceed quota but would have to work very hard to do so.
Option 2, early startup with funding, 30 people. $150K base, $150K variable. Roughly 1% equity (options), on a standard 4 year vest. Would have full autonomy to do what I think would work, plus would be a seller in the early stages. The whole pitch is a fast exit. Founder openly says he wants to sell in the next 1 to 2 years once they hit a revenue milestone (that they’re currently a few multiples away from). Sales motion is admittedly still being built and not successful yet although there is strong product market fit. Upside case, if it exits well, is somewhere in the six to seven figure range on the equity. I’d have real autonomy here and basically own the go to market in a vertical I’ve been in before.
I’d have more fun at option 2 I know it, and financially I can take a risk at the moment. Would love to hear everyone’s thoughts.
What would you need to see from the startup to make it worth the risk?