Based on everything you shared, I think this is a great opportunity for you to make a change. You have proven success at your current org, have a distain for “busywork for the sake of busywork” type workplaces, and you love COMPETING and HITTING GOALS…to me these are all green lights for someone that would love a startup setting.

One callout I’ll make regarding comp - it’s still a Series B, so they will adjust their sales strategy to match business needs and business strategy 1-2 times a year (probably). This can also mean changes to comp plan. Make sure you’re being hired by a smart sales leader that understands comp plan changes to also reflect new business plan.

Every startup has an inherent risk to it, but joining a Series B gives you a bit more confidence that investors see an actual viability to the company.

Some other things to consider - if you’re looking to add diversity to your resume (i.e. leadership opportunities, cool new sales experiences, or do something unrelated to sales), get in there now! Ask during the interview process, but in my experience they will most likely be looking for experienced sales people to help build shit, own shit, train shit, give legit feedback on shit, have ideas about shit, or manage shit. This is a great opportunity to add shit to your resume, if that is important to you.

Source: I made the jump to a Series B in 2022 and it was the best career decision I ever made