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I'm tailoring my resume over and over to highlight my experiences that best fit the needs of employers as described in their job listings. Not to overstate the obvious, but I do this by choosing bullet point items (sentence length) from various previous versions of my resume, developing new items as appropriate and tweaking the word choices and order to give the resume a "voice" that fits the advertised culture and the industry.

A cover letter is supposed to be written for each employer and tell them a story about why I'm a good fit for their opening. A cover letter should not simply restate information from my resume in paragraph form. Again, I create new cover letters based on paragraph chunks of previous ones.

What can I use as a database to manage the sentences and paragraphs from all previous resumes and cover letters, that will allow me to select the ones that I've already used and compile it into a new, tailored resume or cover letter, and provide me with material to develop new bullet points and paragraphs, without having to open all of my previous versions and start copying-and-pasting?

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    A spreadsheet program plus mail merge should get you started.
    – Lauren-Clear-Monica-Ipsum
    Commented Jun 27, 2019 at 9:51
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    I do a similar thing as @Lauren Ipsum -- I have a spreadsheet with some of the most used phrases. Most often, like you, I start with my closest-matching cover letter, highlight what needs to change, add words in red to indicate points of what I want to communicate, and edit from there. It may be useful to check out college career-help department's pages: they often have a list of useful resume verbs -- they may also have similar tools. Otherwise, TWINE, the "choose your own adventure" writing web-app may be a good place to store and mix data?
    – April Salutes Monica C.
    Commented Jun 27, 2019 at 15:30
  • Thank you both for the suggestions.
    – yehoshuk
    Commented Jun 27, 2019 at 17:57
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    For a low-tech solution, you might try creating a master resume that contains absolutely everything and when it comes time to submit your job application, simply make a copy and delete the parts that don't pertain to that job. If you write new content, simply add it to the master.
    – Adam J Limbert
    Commented Jun 28, 2019 at 3:01
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    @NofP I'm a django dabbler, dangerous enough to get a project like this started, but not enough to be sure that I could quickly get it over the V1.0 finish line. You do raise a great point though: this may be more of a tech question than a writing question. Thanks for that thought!
    – yehoshuk
    Commented Jun 28, 2019 at 20:29

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Personally I use an Excel workbook; the individual spreadsheets hold certain thematically divided elements like opening sentences, skills, personal qualities, relevant experience, etc... Within those spreadsheets there are further divisions based on the type of job I'm applying for, so a block of skill-sentences for desk jobs, a block for workshop positions etc... Creating a given resume or cover letter is then a fairly simple matter of looking at the job description and selecting the sentences to copy and paste into a Word document, or similar, that has the set elements of name, address, signature etc... and editing a little to get the "fit" smoothed out. I then save the finished work as a PDF if I'm using it online or just print it out for a hard copy.

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