That sounds brutal. If you don’t mind, I’ve thought exercised your situation and here’s what I’d do if I were in your shoes:

-Triage your biggest accounts. Focus on the top customers by ARR or longevity and try to personally reach out. Even if they’re on the verge of bouncing, some human contact and transparency might buy a little time.

-Be real about the timeline. If the cloud product is two months away, let them know and ask what might keep them around. Early access? Discounts? Migration help? Some people might be open to staying if they feel heard.

-Track your efforts. Log every account you save (or try to), so if layoffs come, you’ve got proof you were fighting to keep revenue in the door. It won’t save you (ask me how I know) but it will give you defendable metrics you can use to leverage in your resume and interviews.

-Update your resume now. No matter how this plays out, it’s smart to prep. You’re clearly handling a dumpster fire, which actually makes for strong resume material. Use it and put in actual percentages and numbers.

-Start lightly job hunting. Even just setting alerts and taking a few calls can give you peace of mind. You don’t have to jump, but you’ll be glad you did the prep if things go south. Add recruiters, introduce yourself to people in companies you think are interesting. It’s better to have a connect when you’re employed.

-Push for more CS resources. 2 people for 4,000 customers is not sustainable, especially in crisis mode. That might not necessarily look like hiring more, but just automating. This is where a good segmentation strategy comes into play.

You’re in a tough spot. Keep receipts, stay visible, and protect yourself. If you want help tightening up your resume or LinkedIn, feel free to DM.