Pros
Upland is broken into 5 BU's which are all very silo'ed. I loved my BU - great sales reps, CSMs, SEs, Professional Services, Marketing...everyone. What a fantastic team. I will miss that group.
Kontras
Upland is essentially a PE firm masquerading as a software company. They've never built a solution and now have 30+ (often ill-assembled) solutions across 5 BUs. As such, they operate much like a PE firm. There is no innovation once a company is purchased. This has led to a 90% stock price decline. New sales management hasn't helped, shifting away from a consultative sales model to more transactional sales by a digital (aka inside) sales team. Add to that the lowered comp and higher quotas (literally having to sell more to make less), and a one can see how Upland's sales continue to decline. This will make paying off a $500M loan in early 2026 almost impossible. If you're in sales, the short-term outlook is fairly rotten. If you're anywhere else in the company, the long-term outlook is downright dismal.