Should Cover Letter Address a Weakness?

I would suggest not to highlight that fact in your cover letter, instead you should sing about your achievements. Your work experience should tell the story in your resume.  I look at resumes all of the time and my positions also say that I prefer a degree.  I purposely don't look at the education section, because I want to judge my candidate based on accomplishments outside the academic arena in the real work world.  We have quite the interview arsenal with pretesting and panel interviews, so once we have a good candidate, we know they can do the job we need them to do.  I'm often surprised with some of our superstar candidates when they later reveal in an unrelated conversation that they don't have a degree.  It depends on the employer and their needs, but if the education thing is important to them and you have all the other qualifications that they want, it would be up to them to ask you more.

Lemme see - you have 19 years at a Big 4 firm, and you advanced to a sr. manager position.

So chances are good that you have a whole slew of  specific and quantifiable accomplishments that are going to b e much more relevant to job performance than a degree.

You've been in the workforce long enough that having a degree isn't a strong indicator of ayhting having to do with your day-to-day job.

That's the good news.

Here's the bad news:

Not having a degree gives the screener a reason to screen you OUT.  And if they're going to use that as a measure, there's really not much you're going to do about it.

Me: I'd still apply.  And I'd try to get their attention with my cover letter.  And if they STILL screen me out, well, that's life.

The only thing you can do is to apply to LOTS of jobs to try to get the odds a little more in your favor.

Good luck!