What are reasons that a company would look to do a major re-pricing of B2B software? Should it be considered a red flag (aka getting more money out of customers because of low rev growth otherwise) or are there other reasons why this is something a company would pursue?

It is rare for companies to engage in a major re-pricing if the problem is low revenue growth. The reason it is rare is because low revenue growth is seldom a function of under-pricing and more often a problem of poor product-market fit OR a saturation of an existing market OR a malfunctioning sales engine. 

Top reasons for major re-pricing: 

1. Your product value prop has changed substantially. In 2018/19 timeframe we changed the pricing structure at Helpshift to a volume-based model from a seat-based model as our product had evolved and one of our key new features (chatbots) saved a lot of time in agent productivity. A seat-based model would not work for us since the effective use of our software could have led to reduced agents in an organization. 

2. You are consistently inflating list prices. If your pricing structure isn't built properly, you will notice that your sales reps will start inflating the list price. Their compensation is generally aligned with getting the max obtainable revenue from individual customers. Therefore -ve discounting a very strong signal. 

3. You are selling to a new segment. The same software we sold at Medallia circa 2016 could have been sold for ~500k or for 5M, depending on the industry and size of the customer. Financial services firms can often pay more but have different needs than Retailers for e.g. You will want to re-package and re-price your product from time to time to create the best offers for new industries. 

4. Your competition has changed substantially. Some industries like sales-tech, mar-tech or customer support software are very crowded. New entrants are trying to find their way in, often by undercutting prices. This creates commoditization and price pressures for incumbents. In this case, if you don't re-look at your entire offer, you are at risk of "looking" less competitive.