Pros
Upland has a 100% customer success commitment. Management and employees are sincere about that operating principle and that is evident by their very high customer retention. Upland cares about its customers and works hard to earn their business. Most of the employees work from home, and there are some terrific people at Upland. While they offer "unlimited" PTO, you need to realize this is not a benefit for you. It is a benefit for Upland. Paid vacation time accrues as a liability on a company's balance sheet. And besides the impact to the finances, once Upland terminates you (and eventually they will), they must pay you accrued vacation time. "Unlimited" PTO means they improve their balance sheet at your expense. If you are just starting out on your career, Upland may be a good place for you. You will get a paycheck, and learn some skills. If you are a seasoned professional, you will be frustrated from day one.
Cons
A slumlord acquires cheap apartment buildings, does nothing to fix or update them, and lives off rents and lease renewals. Upland acquires software companies on the cheap, fires most of the employees, and lives off he license renewals. They invest little or nothing in any of their products. While they do update some products with 2 or 3 releases per year, they will tout "exciting features" such as the "fascinating" ability to choose status from a drop down box rather than enter free form text. This is what is considered "innovation" with Upland products. There is little to no organic growth. They have no strategy for acquiring new customers as their business model is built on renewing existing customers and trying to cross sell additional products from the acquired companies. While there is customer attrition every year, it is made up with the new customers they get with every acquisition. Upland employee policies are cheap and penny pinching. They try to hire many people as a 1099 consultant so they do not have to pay benefits. They will tell you "It is only for 3 months." Many who fall for this trap stay on as consultants - in fact, a good number of the Upland "employees" are consultants. If you get hired as a salaried employee and start in the middle of a pay period, they will deduct your benefit payments for the full period. They do not prorate, so you wind up paying for benefits before your hire date. If you are terminated in the middle of a pay period, you will be paid up to that day and not to the end of the period. For new employees, there is no new hire onboarding or orientation. You will be given a computer, and you are on your own. There is an employee portal that may help you get up to speed, but it has not been updated in years. There are few documented processes. For example, if you need to travel for work, good luck finding the travel and expense portal...there is none, and there is nothing documented to tell you that. Upland does not offer a 401k match. If you do have a 401k, you will have occasional issues. One day, you may notice less was added to your retirement account than what was deducted from your paycheck. You will spend 3 weeks trying to resolve the issue. Other times, you may see the contribution added to your account a week after your paycheck. Good luck trying to get an explanation.