Weighing Job Offers - Series B or Series E (close to IPO)

Hi Savages - I'm making a move after 3 years in my current role. I'm in the final stages with 2 companies and struggling to decide between them ... any advice on things to consider or thoughts on how the current market could impact selecting an early vs later stage startup?

• Same OTE
• Similar industry - same niche of Information Security I work in now so my network + experience carry over nicely

My goals are to be an individual contributor selling increasingly expensive stuff for cool companies, and build a high level of expertise in a niche industry. Both options align with that objective. Anyone have a crystal ball?

Company A: Very close to IPO, Great RepVue scores, ~1400 employees, solid reputation in the market and mature processes + a suite of several products. Some local presence so I'd have coworkers nearby but don't HAVE to go into an office. Enterprise Hunter Role with ~150 target accounts. I'd get equity but I don't expect it's going to change my life... if the price dips after IPO could I end up penalized somehow between taxes and reduced value stock?

Company B: Freshly funded Series B, I'd be the 5th sales rep (HUGE patch - Mountain + Pacific time zones) and the 80th employee - they have some solid deals in the pipeline that would transfer to me so I'm not starting from scratch. The tech looks really good (1 core product/platform) and I'm not aware of any solid competitors. I was about the 80th hire in my current role and there is something fun about helping build the foundation but I'm sure it will be totally bonkers. Not many female employees right now (I am a woman) - maybe 6 based on LI.. Very likely less work/life balance vs Option A BUT higher risk/reward.

Thanks in advance for any insight you might be able to provide!