LTI should outline precise follow-up procedures, including when to call and even what to say. That's the crux of the conflict. LTI needs to make collections part of every sales person's job. Commissions and bonuses should be tied to actual payments received rather than orders taken. Fear of asking for payment.
Money can be an uncomfortable topic, even for a sales professional.
So Jim waits too long to bring the subject up. Making sure it actually happens is the bigger challenge. LTI needs to build in a reporting mechanism to ensure it does. When the invoice goes out, Jim should call promptly to confirm that it was received and ask if there are any questions. Allowing yourself to be taken advantage of or lied to.