Cover Letter Dos and Don’ts: Startup Edition

By    April 4, 2013

resumes

Remember those classes and tutorials you sat through in college about proper cover letter and resume writing that included everything from using a formal, “To whom it may concern,” to including an “Objective:” section in your resume? Take everything you’ve learned and throw it out the window, because it’s wrong–if you’re applying to a startup, that is.

Startup culture is infinitely different from that of big companies and corporations, a rule that trickles all the way down to the kinds of cover letters and resumes that actually catch a startup’s eye. Most cover letter guides online tout factory templates and stale instructions like, “summarize your strengths,” and “make a connection.” It’s good advice, but forces you to write within the confines of uninspiring instructions and forget that you have the freedom to be yourself. Many startups view keeping their culture intact as a number one priority, so coming across as a robot in your cover letter is the last thing you want.

We can’t guarantee that these techniques will go over half as well if you’re hoping to break into Wall Street. If you’re keen to work at your favorite startup, however, here are some dos and don’ts for applying, straight from SpareFoot’s amazing recruiting specialist Rachel Morse.

Tailor your cover letter to the startup
Copy-pasted cover letters are the biggest turnoff for any company–if you apply for company X but mention company Y in the concluding paragraph, why should company X even consider you? You’re obviously shopping your cover letter around. Next!

Instead, do your research on the startup of your choice before you apply–read their blog, follow them on social media, and take the time to get to know them, even if it’s from afar (I recommend listening to Every Breath You Take for inspiration). This gives you an idea of the culture of the company and how you could tailor your resume to them specifically. Do your homework, do your research, and it will show in your application. Sidenote: the jury is still out on whether or not you should tell your interviewer that you saw they liked The Walking Dead on Facebook, and that you are also a fan of Rick Grimes’ cry-face.

If you’re applying to SpareFoot, for example, you should know from our blog that we love beer, self-storage, and pushing the boundaries with our sexy bodies. Touching on any of those things in your cover letter lets us know that you took the time to do the research, and makes us want to take the time to get to know you back.

Be upfront
Don’t hedge and throw in abstractions about what you think you might want; most startups don’t have time for wishy-washy people who can’t jump in, start learning and contribute to the company. Know what you want to accomplish, where you want to go, and what or who you would like to work with in the company.

“Be really upfront with what you want out of the position,” said Rachel. “And tell us about your relocation needs: when you are moving and your plans for getting to Austin, if you’re not here already.”

Don’t be afraid to be yourself
Are you just a naturally funny person? Don’t be afraid to slip that in! Do you play the banjo in your spare time? Tell us about it!

“Remember to get as much of yourself into your cover letter as possible,” said Rachel. “If you have a fun hobby, quirk or special talent, tell us about it. Don’t be afraid of being really different, because a generally well-rounded and interesting person will go a long way. People who are amazing at their jobs are usually also amazing in the real world.”

Stay away from buzzwords
Here are some of the red-flag words and phrases that Rachel sees on a daily basis and advises against using:

  • “Mrs. Morse” – Don’t call me Mrs. Morse. Please just don’t.
  • “Entrepreneur” – This word is thrown out so much. I just want a benchmark for it. Chuck is an entrepreneur; a college guy with an idea for their app is not.
  • “Techie” or “Nerd” – Introducing yourself as a techie or nerd is overdone.
  • “Go-getter”
  • “People-person”
  • “Detail-oriented”
  • “Anal”
  • “Getting my foot in the door” – Have some drive or direction, know what you want.
  • “Seeking new challenges”
  • “I’m exactly what you’re looking for” – Can you really determine this for yourself?
  • “Real world experience” – Everything you are going to get is “real world;” this is real life. Plus, I just keep thinking, “Seven strangers…picked to live….”
  • “Tenacious” or “Relentless” (for sales) – Now I’m scared of you.
  • “Spread my wings and fly”
  • “Diamond in the ruff” – Especially if the last two are in one cover letter.
  • “Above and beyond”
  • “Giving 110 percent”
  • “Professional appearance”
  • “Passion for success” – As opposed to hating success?

Don’t just take Rachel’s word for it, however. I asked two SpareFeet to send me their list of cover letter and resume no-nos:

Marketing pro Rachel Greenfield:

  • Typos
  • Grammatical errors
  • Poor or awkward writing in general
  • Generic Unsuck It-style “business” jargon
  • Vague-ness of any kind. Be concrete and real.
  • A super long cover letter.

Co-Founder Mario Feghali (note: he still has not found his sweaters):

  • When the application says “PLEASE INCLUDE A COVER LETTER” and the application doesn’t include one.
  • Cover letters for the wrong department.
  • Applying for one job and referencing another.
  • Saying things like, “I’m a hard worker, team player, self-starter and strategic thinker, who always gives 100 percent.” Buzz words don’t tell me anything about a person.

There are exceptions to the last item on Mario’s list, of course. His example:

“I’m a hard worker: I once stayed up for 72 hours and ran 28 miles in the snow while carrying a wounded pregnant lady to the hospital after I saw her car go off a cliff.”

That, according to Mario, might just cut it.

Tell your story with the resume
“We all have to try to tell a story with our resumes,” said Rachel. “Make it easy for someone else to understand your story.”

Avoid putting confusing time ranges and dates into your resume; you want the person reading it to get a clear sense of your timeline, not wonder if you’re a Time Lord. Additionally, be able to explain long gaps between jobs, as well as hopping from one job to another too frequently.

“Unless you have legitimate reasons for leaving a position every six months, we’re worried.”

And save your crazy inflated titles for your last job–we don’t believe in internal titles anyway.

“A lot of people, mostly those who have worked in startups before, will have the word ‘ninja’ after their title, like ‘Architecture Ninja’ or ‘Engineering Ninja,’” said Rachel. “If ‘ninja’ is in your name, be able to articulate and explain what it is that you did–otherwise we’re really going to think you were a ninja.”

Finally, as we (and everyone from your professors, to AutoCorrect, to your mom) have stressed time and time again: proofread before you send! If you need more convincing:

“One time someone put ‘youporn.com’ into their resume,” said Rachel. “I’m pretty sure he was copy-pasting without thinking about it, but all the same–awkward.”

Don’t forget, SpareFoot is hiring! Also keep an eye out for our official Recruitment Video, coming soon to a Youtube screen near you.

Jenny is part of the marketing team at SpareFoot. She currently lives in Austin, TX and likes sushi, Faulkner and Asian horror movies.

  • Craig Barrett

    I am going to add “Guru” right alongside “ninja”. Unless your cover letter is in Sanskrit, you are not a guru, you are just some goon who thinks you are better at social media than you are. And you should probably be stabbed.

  • http://thestoragefacilitator.com Rachel Greenfield

    Yes!!!!

  • juliebarbee

    Who do you recommend addressing the cover letter to? CEO, head of HR or the person the position will be reporting to?

  • Rachel Morse

    Good Question! CEO if you are applying for a director position, and hiring manager for everything else. If you’re unsure who the hiring manager is, check out which LinkedIn connections you have with someone in that company and ask them! Best case scenario, you get the right name and some insider information about the position and company.

  • Resumes and Cover Letters

    As of my experience I have periodically posed questions where the answer should be ‘No’. For example ‘Do you have a work ethic that is questioned by your superiors?’ or ‘Are you applying for this job without reading the description?’

  • Ashley Dillin

    This is awesome advice. Wish I had been brave enough to implement it a little more in my application, but I’ll definitely be using it from now on!

  • Sean Hisaka

    This was a hilarious insight to something I’m doing right now. I have to disagree with only one point, as I start off every cover letter with, “No Carl, nooooooo.”

  • JB

    I just wanted to say thanks for this post. I’m currently on the job hunt, and I have a strong desire to work in a startup culture. I’ve used your advice to write three cover letters. So far, I’ve landed two interviews and a test project request within one week of sending out emails. I’m so excited!

  • Jenny Zhang

    That’s really exciting, congrats! I hope you get some good news :)

  • Jessica Gillespie

    Thanks for writing this post, Jenny! It was helpful to me even a year after you published it as I apply for jobs with start-ups. I definitely incorporated more storytelling elements in my resume even formatting my resume so that the reader can get a better “picture” of my overall experience. A cover letter seems even more essential for startups as they have a unique culture and environment and team makeup compared to most corporate jobs. For example, a startup company may be a team of 4 working without desks (rather on a foosball table) in small communal spaces where the perks are drip coffee and the team likes to have their meetings during a team bike ride. Most startups will make it a high priority to find the best fit when its time to hire someone not just because hiring costs money but because they have an idea of what they’d like the culture to be and what types of people, skills and interests can help the company evolve. I say ALWAYS write a cover letter for a start-up even if it’s not required and try your best to stand out. Share something impressive about you and try to insert your personal experience and philosophy alongside your work history and accomplishments. You never know with startups what exactly will jump off the page for them!

    Jessica
    http://about.me/jessica.gillespie

  • http://hurmoth.com/ Hurmoth

    Thank you so much for the post, and even more importantly, thank you for the Time Lord reference. I cracked up when I read that and then realized that some of my past cover letters probably did come across like that.

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