Desktop Application Software

The Setup
The client makes a software product that manages desktop applications across different machines. There are 2 broad categories – large organization (with 1000 + computers) and small organizations (100 – 1000 computers) that use the software. Client has a strong presence in the small segment but has not been able to penetrate the large segment

Question
1. Why is the client not able to have a footprint in the large segment?
2. What recommendations would you have – stay / exit the large segment? What tactics would you use if you decide to stay?

Additional Info
Client software is extremely stable and has clear benefits because of reduced system outage. These benefits are more for large companies than for small companies
Client sells the software, retail stores sell support services at time of sale.
• Retail stores sell using a direct sales force that visits the large / small companies.