The short answer is, Yes, you definitely need a cover letter. Will someone read your cover letter? Maybe.
First and foremost, the cover letter serves as a crucial piece of your completed application and may send red flags if you do not have one. An incomplete application will, in most cases, eliminate you from being chosen in an applicant tracking system, like most large districts utilize. Not providing a cover letter also suggests that you may not be serious about the position.
When applying for a teaching position, use the cover letter to elaborate on HOW your skills and accomplishments will benefit your new potential district. Use talking points from your resume, but try not to echo too much, as a cover letter is meant to be more a of narrative vs. a listing of qualifications.
Also, use the job posting(s) to find out what the position is looking for, and elaborate on those characteristics the most. Research the district and school to find out what they're already good at and then, what they may need help with. This information could be helpful on your cover letter and in the interview.
While the overall set-up of your cover letter won't need to change much, it is important that you take the time to personalize the letter for each new job to which you apply. It helps to double and triple check that you have not left any details in the cover letter from previous applications (school name, position details, etc.)
More importantly, personalizing the cover letter will show that you have taken the time to learn about the program, and will allow you to demonstrate specifically how you can benefit that organization.
If you are transitioning out of teaching, the cover letter is even more important. It will serve as the explanation of how your teaching skills will help you, and the company, in your new role. Most people outside of education have no idea what teachers really do, so it is very important that you target your transferable skills and explain how those skills relate to your new field.
Lastly, if you are writing your cover letter as the body of an email, be sure to also include it as an attachment in case they want to print it out. Your letter will look much more professional as a PDF than an email printout.
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