Pros
Passionate, interesting, creative people working there in support as reps and as leads. Learned a lot from my lead. When I started I came from an unrelated field with no tech experience. Very modern and creative office with a cool vibe. A lot of benefits in the Chicago office - reimbursement of CTA, free lunch/breakfast daily, free kombucha, coffee, cold brew, fully stocked bar with beers on tap, fun office environment (a lot of times we played beer pong or flip cup on Fridays). Company parties and holiday parties are always at a great place. Pay is generous for the starting roles - significantly more than you'd be paid at any other entry level support role.
Cons
Upper management in the support office in Chicago...period. Little to no support provided to support reps and middle management - yet high expectations. There was such a large gap between the support reps and leads and upper management that it made working there unbearable. Things were always changing but never properly communicated, which created confusion and chaos. Each of the high level managers at Venmo has demonstrated glaring red flags for why they don't belong in people management. None of them are particularly skilled with managing people. Employees are afraid to speak up because upper management can be vindictive or respond to serious concerns with dismissal or vague and empty claims to address the issue. The issues are almost never addressed the way they should be, until the entire company speaks up and demands change (which did happen at one point). Upper management demands very specific numbers and results from support leads, but hilariously enough, they don't know much about the product themselves. As an example, when each of these managers were asked to do a "day of phones" or a "day of emails" for fun, they sat by all of the support reps. We watched them do our job. One manager wasn't sure how to take notes after a phone call and save them, or how to add a tag to categorize the call - they had to ask a rep. The irony was this same manager was insisting the support reps summarize and take notes after a phone call in 1.5 minutes or less. They were also demanding 10 calls per hour, yet not one of the managers was able to produce that while acting as a customer support rep. To me, if you're in a management position, you should know the product and processes like the back of your hand. If you are demanding specific results from your team, you should be able to deliver those same results. I do want to note that there is a very high level manager above the upper managers who is a wonderful, sincere and professional person. No one ever had a bad word to say (that I ever heard) and they are respected in the office. Unfortunately, they were not as directly involved in Venmo's day to day and we were directed to go to the managers who worked on our side.