Company run by the numbers...but bad at math. (legal harassment of ex-employees) - Professional Services Upland Software Employee Review

Great remote first mentality. Great supportive people. True common sense, unlimited PTO. Good culture.

Salary & Benefits are likely lower than at other companies for similar roles.

The PTO policy is excellent, and there are genuinely great people throughout the organization. Many employees work incredibly hard and care deeply about customers and their teammates. My direct manager was one of the best leaders I've worked with. She invested heavily in coaching, development, and creating opportunities for her team despite having very limited support from upper leadership. The lessons I learned from her continue to help me succeed today. I have since moved into a different role, and much of what makes me successful today comes directly from her leadership and coaching.

Marketing and Sales were rarely aligned. SDRs were expected to generate pipeline from campaigns, messaging, and initiatives that often felt disconnected from what was actually happening in the market. There was a constant gap between expectations and reality, making it difficult for teams to execute effectively. The company had no real enablement function for SDRs. Training, onboarding, coaching, messaging, and career development largely fell on frontline managers. Both SDR Managers did everything they could to prepare and develop their teams, but they were forced to build much of the process themselves with limited resources and support. Product positioning was another major challenge. Many of the solutions felt outdated compared to competitors, making prospecting and value based conversations significantly harder than they needed to be. SDRs were often expected to create excitement around products that struggled to keep pace with the market. One of the most frustrating aspects of working here was watching exceptional leaders and high performers receive little to no recognition while others seemed to advance based on visibility rather than results. My direct manager was, without question, the best part of the SDR organization. She brought great energy every single day, knew the company, products, customers, and processes inside and out, and genuinely cared about helping her team succeed. A lot of what I apply in my current role, and a big reason I'm one of the top performers on my team today, comes from what she taught me. Unfortunately, instead of being empowered to lead, she spent a significant amount of her time dealing with leadership issues, organizational dysfunction, and problems created above her pay grade. Despite everything she contributed, the recognition and support she deserved never seemed to come. Frankly, I have no idea why she is still with the company. The larger issue was leadership within the SDR organization. The SDR Director may have had good intentions, but lacked the people skills and leadership abilities required for the role. There was little evidence of manager development, strategic direction, or the ability to effectively lead through change. Instead of making life easier for frontline managers, leadership often created additional challenges they had to work around. Managers spent far too much time managing upward, navigating organizational dysfunction, and compensating for leadership gaps rather than focusing on developing their teams. The reality is that many of the team's successes happened because of the managers, not because of the leadership structure above them. The strongest reps succeeded because they had managers who cared, coached, and fought for them, not because they were part of a well run organization. Outside of a handful of exceptional coworkers and managers, the company often felt disorganized, reactive, and disconnected from the realities of the market. The people closest to the work understood the problems. Leadership either failed to recognize them or lacked the ability to solve them.