The problem with the situation as posed is that, as you've found, airlines don't fly transcontinental red-eyes from East to West. Because flight time averages around 5 to 6 hours, you're looking at an arrival time just 2 or 3 hours later than take-off, at least in adjusted time. That means that any late-night departures will drop passengers off in the wee hours of the morning at their destinations. Even if local landing regulations would allow this, there wouldn't be a huge market for it at all. To get passengers to arrive early morning on the West Coast, obviously, would require a wee-hours take-off, which faces the same challenges.

Unless he's up for hiring a private jet, your boss is going to have to change an appointment at one end. My suggestion is that he move back the SEA presentation to noon and take the early morning Alaska Airlines flight out. It leaves Reagan at 8:00 AM and arrives Seattle at 10:50 AM. Let us know what you decide!