Comment Targeted Resume and Cover Letter FTW (Score 1) 472
You probably need to take a serious look at your resume. Even as an 'old guy' with plenty of great experience you need to have a two page resume. Update to a modern template and spend some time honing the message to target the job you want. Hiring managers understand that you have more under your belt than could fit on your resume so don't sweat what you can't fit.
Focus on results. Use the space wisely. Don't get disappointed when you don't get an interview for a job that emphatically states the need for a degree. If their culture does not allow for someone in your shoes you probably wouldn't be happy there anyway. There are senior level technical jobs that will accept experience in lieu of a degree. Look for them.
Also, don't be afraid of selling yourself. Don't lie, never lie. But do use compelling language to indicate that you get the job done right and under budget.
Finally, create a cover letter specifically for every application, especially if the jobs sounds like one you really want. Forget about the resume in the cover letter. Use 2-3 paragraphs to call attention to the specific experience and results that apply directly to the job. Come off as confident but not cocky. Remember, you are the experienced professional.