Help me decide!
I have two job offers on the table that I need to decide on by Monday. They both have positives and negatives but they all seem to cancel each other out in some way or another.
help me choose, give some advice or feedback please.(For reference this is my first tech & first sales job).
Job 1:
- 55k base / 20-25 commission (uncapped)
- mostly inbound (40 calls per day)
- Sells almost totally to enterprise customers
- 1 day a week in office
- Quota: 4.6 meetings (so 5 gets accelerators)
- Older brand, less techy product, more solutions based. Much easier to learn. (AI Portfolio Management)
Job 2:
- 55k base / 15k commission (uncapped)
- mostly outbound (75 calls per day)
- sells mostly to SMB and some MM
- also 1 day a week in office
- quota 6-8 meetings (less easy accelerators)
- newer brand, much more technical (IT observability)
Important extra context:
Job 2 will allow me to do the first 3 months remote (it’s not in my city), which is great because I live with my GF who has one more semester of college, so if I leave for the other job, we’ll have to do long distance. BUT that means if I do the remote training I’ll have to learn the ropes and the technical aspects all while being not in office (I learn better in person and I’m not super techy).
Job 2 also has “micro promotions” in the SDR path that come with pay and quota raises, but it kind of seems like a way to prolong getting to AE.
So at the end of the day, is it better to have enterprise experience or technical experience? What to choose?
Posted Jul 10, 2026, 5:58 PM UTC