- "Inbound" -- I chuckle everytime I see someone on LinkedIn say they were just hired as an Inbound AE. What they mean by that is, you get 1-2 DECENT leads a week and the rest of the leads are recycled from AE to AE. You are more outbound than inbound (i.e., get a lead, search the URL, start hitting up that company, etc.). Sad thing is they held off for so long to buy tools for outbounding (Sales Nav, ZoomInfo) but will spend $16M on a SuperBowl ad that generates zero traffic. Laughable.
- Sales Strategy -- AEs are comped only on Annual deals, I can get with that. However, every option plan besides Enterprise is offered monthly. Why wouldn't a company that is deciding between the other 20 PM tools just go monthly? The problem, ClickUp recognizes a monthly purchase as ARR... so if you want to upsell them you need to push a higher plan or more licenses. Oh and you are selling Enterprise on permission settings.
- Leadership is suss. VP is cool. CRO turned CBO is clueless and it showed at SKO. He confessed that the annual # was made out of thin air. Nice, so my quota and comp are correlated with a # that was probably napkin math. He has zero SaaS selling experience. Was moved to CBO because he isn't a CRO but is still boys with the CEO so he had to do him right.
- Equity -- been a part of some cool startups and know that the EP is always going to favor the company but holy smokes if ClickUp doesn't want the biggest slice of the pie, I don't know who does. Easy to quit when you have zero skin in he game.
