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This was kind of a silly idea of mine when I was first starting out as a totally inexperienced web designer, which I’ve kept updated as my career has progressed. When I first built it, besides being penalized by my sparse newbie resume, I was doing my job search in the designer-saturated Bay Area during the height of the economic downturn, sending cover letter after cover letter. I got so sick of tailoring dozens of cover letters a day with almost the same content in a slightly different order. It seemed like such a pointless task, especially when it often ended in rejection anyway. And it seemed to me that good designer should be able to design a way out of tedious soul-crushing tasks like that.

So I dissected all of the cover letters I had written over the last month. I looked at what skills I was trying to demonstrate with each sentence or anecdote, and picked out a couple that I thought encapsulated the most valuable skills I would personally be bringing into the workplace (because why work at a job that didn’t want my actual skillset?). Then I looked at my cover letter’s users: the companies I was applying to. I dissected all of the job postings I was most excited about and searched for what deal-breakers they had listed and what skills they thought were most important. I wanted the perfect cover letter.

But the perfect cover letter is perfectly customized to the job posting and the company. But from my dissection process, I had a list of attributes paired with anecdotes. I built a javascript tool that would allow me to quickly rearrange these anecdotes by dragging-and-dropping or deleting the paired keyword, to perfectly match the criteria listed on the job ad. I added a fields to let me customize the overall focus, company name, and addressee of the cover letter. And of course I included a disclaimer at the end about how this cover letter was personalized but self-writing, and inviting the reader to explore my tool.

At this point in my career, I’m not blanketing the town with hundreds of cover letters, but the tool still serves a purpose. The hard work of designing and building the tool is already done so I’m happy to take advantage of it, and the back-end of my tool helps me organize my thoughts when writing a cover letter so that each sentence has a defined purpose and my writing is much clearer.

I got my first paid freelance design job within days of creating this tool, and I’ve haven’t had the soul crushing task of manually retailoring a single cover letter since. You can create your own cover letter here.

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