Word Choice

I would probably say:

We've scheduled the project manager to meet with the insured tomorrow...

Thank you!

You're welcome! You could also say:

The painting contractor and insured are meeting tomorrow...

"We contacted the insured and scheduled the project manager to meet with him tomorrow to discuss the painting schedule."

Could become

We arranged a meeting for tomorrow between the insured and the project manager to discuss the painting schedule.

(Obviously if you arranged a meeting, you must have contacted both the insured and the project manager.)

Mame's is best, less is more, 8 words to Seizan's 18.