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Strengthening your job application

City Year Headquarters building, located in Boston, MA.

Job application tips

When applying for almost any job today, filling out applications and submitting your cover letter and resume usually mean that you’re representing yourself on paper before you even get to meet future employers in person. Although this process can seem daunting during your job search, there are many small steps you can take to make a big difference, transforming the first impression you make on future employers from good to great!

Here are a few tips from the members of City Year’s Talent Acquisition team—the people who facilitate the hiring process of hundreds of City Year staff and senior leaders at Headquarters and across 29 U.S. cities each year—that will help you confidently craft a great cover letter, resume and application and help you put your best foot forward when trying to land that dream job.

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Explore current staff openings across the City Year network.

Why write a cover letter?

Some believe the cover letter is dead. We disagree. At City Year, we love to read your cover letters! Your cover letter gives you a unique opportunity to get specific about key experiences that qualify you for the particular role you are applying for and control your own narrative about how you will add value– definitely take advantage of that! Try to make sure, however, that your cover letter is one page long or less. Short but sweet is a good general rule to follow!

Choose your words carefully as you show your commitment to an organization, mission and specific position. It can be sometimes hard to decipher a pattern or overarching skill set in a resume. Your cover letter can tie up your experiences with a bow and show the kind of impact you would like to have in your next role.

Telling your story

How would the role you’re applying for be a part of your career story? Do you bring a unique perspective, inspiration or approach to your work? Use your cover letter to share these details and help us get to know you better as an applicant and possible future teammate!

Cover letters can also be incredibly useful for those looking to change careers because you can show your career path and connect skills that might not seem related on the surface.  Your cover letter and resume shouldn’t present the exact same information; instead, they should complement each other.

For example, serving in public schools as an AmeriCorps member and working at City Year headquarters in fundraising are very different jobs. However, both require some similar skills, particularly the ability to develop strong relationships. If you are trying to transition from one job to the other, you could share in your cover letter an example of a transformational relationship you cultivated, what you learned from it and what your approach to building these kinds of connections would be in your new role.

Quantify your impact

While your cover letter outlines who you are and underscores your interest in the role, your resume is a great place to show your qualifications and skills. Look for areas on your resume where you can use data or statistics to demonstrate your success.

For example, if you were a classroom teacher, how many students ended the year at or above grade level? If you worked in development, what was the size of your portfolio? How did annual giving participation increase? City Year strongly believes in the power of data. Numbers and examples of your impact demonstrate your track record and how analytical skills apply to your work.

Applying to multiple positions

We’re so excited that you’re interested in multiple roles or locations at City Year (or anyplace else you may be applying)! Please review each department description for all positions to learn more about what might be best for you and to customize your resume and cover letter as needed. Each City Year site and Headquarters conduct their own hiring so if you are interested in a similar role at two sites, please apply to both.

Edit to make an impression

Hiring managers usually review dozens of cover letters and resumes for a single role, so we recommend that you make every word count! Try to communicate the essentials and edit out any filler. If a sentence doesn’t communicate something meaningful about you or the role, you can probably remove it.

Your application should present a clear story of your background and why you’re interested in the organization. One strategy is to keep a longer, more comprehensive resume for your own reference. Then, you can customize that version for each position you apply for, making sure that only the most relevant experiences and examples are included.

Before you submit…

Your resume and cover letter can also serve as a writing sample, so don’t forget to take a few minutes to read everything over one last time before clicking submit. Check for consistent tone, grammar, and formatting. Reread the job description to make sure you’re presenting your relevant experience and to see if the hiring team has asked for any specific information to be included.

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Pro tip: Ask a friend or family member who is gifted in grammar, spelling or writing to review your resume and cover letter before you submit them. It’s truly amazing how hard it is for us to spot our own errors … And clean copy makes an excellent impression!

Our hiring team will reach out via email if your application is selected. Most interviews are conducted initially via phone or free video conferencing; any follow-up interviews will likely be in person. Unfortunately, we’re sometimes unable to message every candidate; if your profile doesn’t match the role’s needs you may not hear from the hiring team but we will keep your resume on file and encourage you to keep checking on future vacancies.

Thank you!

Thank you for taking the time to read this and invest in your application—at City Year or another organization you are passionate about. We hope these tips from Talent Acquisition will help you get to know City Year better and help us get to know you as well. We’re eager to review your application and hope you will consider working with us!

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Written by Emma Seibert Wright
Senior Talent Acquisition Operations Manager




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