Pros
You can make a ton of money if you're effective at finding good accounts and put in the work.
It's a very easy product to sell (it's free with no contracts) once you get the hang of it. The product itself is also constantly being approved.
Top to bottom the people in Chicago are great on a personal level--directors, managers, reps, etc.
Want to address a few myths I'm seeing in other reviews:
You do not have to work beyond the required 8-5 schedule if you can budget your time well, find good accounts, and run your Zoom calls effectively. This would be even more manageable if management reduced the amount of mandatory internal calls that don't help drive revenue.
They do not necessarily fire you for missing quota 2 months in a row. If you are at 6% consecutive months, yes, you're probably in the wrong job. If you miss the first month of ramp, which is $1,000 of revenue (compared to ~$120,000 fully ramped) and then miss again the next month, yes, that's probably a good indication that it's not a good fit. Speaking from experience, if you demonstrate you can do the job, they do not just fire you for a bad couple of months. They will also generally give you notice and deadlines if you're at risk of getting fired, even if they don't call it a PIP, although I've heard a couple reps swear that this was not the case for them.
"Lead quality is bad" Yes, the top reps are not using the ~5 accounts Engine's automated "drip" system adds to your book of business in Salesforce every night. You have to find your own accounts. Spend an hour or two every day finding fresh accounts to call. That's part of the job.
I see people complaining that they're judged too much by their "numbers" once they take the job or taking an off-the-cuff "healthy dose of anxiety" comment made half in jest out of context. Yes, welcome to sales. If you don't like being judged on a quota, I'm not sure why you're in this line of work. Leadership cares about you on a personal level, but I'm not sure what you expect if you're routinely missing your #.
"Quota is attainable at first but then gets hard" Yeah, that's how ramp works. You don't get to bring in $100 in total profit margins for the company on hotel bookings every month for eternity and get paid $120,000/yr. If you find a company willing to permanently pay you 1000x what you produce in profit, please refer me. In theory, you can be at 100% of ramped quota by closing a $240,000 account ($20k/mo spender on hotels) every month if you get their full share of wallet and they're steady spenders (not seasonal or event-centric). $240,000 in annual hotel spend is roughly the average deal size reps are pursuing these days anyway, so think of it as closing one slightly above average size deal a month to stay in the ballpark of ramped quota. Obviously you want to go beyond that to max out accelerators and give yourself a cushion, but that's completely manageable. You can also offset 3 or 4 bad months with a single big customer. Most reps in Chicago are hitting their numbers still as they get towards being fully ramped--2 of 4 teams had every single rep hit last month, and the other 2 had most reps hitting. Don't be misled a few upset ex-employees who never even got close to reaching fully ramped status because they either didn't put in any effort or just couldn't put the pieces together.
Cons
In-office 4 days a week at 8am.
Quota capped at 300%, even post-ramp. Never been at another company that operates that way. There are a few reps who have closed enough pipeline that their commission checks would not change between now and Thanksgiving if they went off the grid on a 3 month vacation starting tomorrow. Very weird to set up quota in a way that reduces the incentive to keep bringing in more business or, at the very least, incentivize sandbagging deals.
The training & enablement functions are brutal--thank god they reduced the number of those reps had to attend every week. The people that run them are great on a personal level, but their work product is just not helpful. Wish they had listened to all the reps who pointed out that they were useless earlier instead of waiting for the CEO to join one for the first time ever and cut off the presentation 3 minutes in because it was so painful. Generally speaking, just too many internal calls and exercises that aren't helpful. The actual sales managers (as opposed to training, enablement, RevOps, etc.) know what they're doing; listen to them and you'll be fine.
Some reps complained that we as an office weren't "collaborative" enough across teams, so they've tried several exercises in Chicago to appease these people. First they tried "Wacky Wednesday," which required everyone to switch seats for one day and sit next to reps on other teams (for those of us who keep useful resources pinned up at our desk, this was just an unnecessary inconvenience), then they transitioned to "scrums" where you spend the last hour of your Tuesday a couple times a month role playing in front of the entire office. No one I've spoken to enjoys them or finds them especially valuable. To the extent they are valuable, the goals could be achieved with a Slack message, a few minutes in daily team meetings that already happen, or in a 1:1 instead of these hour-long blocks with the entire office. If someone wants to put together an optional exercise like that, go nuts. Leadership mandates these things to appease a handful of people at the expense of everyone else. We have had visitors from other offices who found the courage to put 1:1 time on reps' calendars to pick their brains and share ideas. If visitors who have never met anyone in the office can do it, so can these people hellbent on forcing the entire office into an activity they don't find useful. There's not a rep in the office who wouldn't help or give advice if asked.