Jeff Devine

I only tell you what to do because I love you

My Cover Letter That Didn't Work

Below is a cover letter I wrote for a job I did not get.

It was February 2011, and I realized I had no desire to continue climbing the corporate IT management ladder. But I also didn’t have the confidence to turn my then-side-project into a full-time job.

The company in question was building the first off-shore IaaS cloud using OpenStack, and I desperately wanted to lead their development/product team. Two long phone conversations and a ringing endorsement from a former colleague led me to believe things were looking up; but then the conversation stopped. In truth,

I had zero experience and was an awful fit for the job, but I thought my conviction and ambition would be enough. So in place of legitimate experience, I wrote a letter to try to prove I was worth taking a chance on.

I didn’t get the job, or even an acknowledgment of the letter, but the exercise of codifying my beliefs was well worth it. It gave me a baseline to measure opportunities against, and a more specific direction than just “not my current job.”

I’m a big believer of archiving everything you produce and periodically returning to it. It is easy to get lost in the day-to-day ups and downs. Looking back and reflecting on where you’ve been shows you if you’ve grown, and if you are still heading in the right direction.

I practiced this earlier this week when I was approached with an opportunity for a job. I had copied bits from this letter to my Careers 2.0 profile, and it seems those bits caught a recruiter’s eye. In considering the opportunity, I decided not to move forward and it was the contents of this letter that helped me come to a decision.

Since I wrote the original letter, I did get the courage to take a chance, and am trying to live what I wrote. It isn’t easy, but I have both a metric with which to keep myself in check regarding my own goals, and also the experience I so desperately wanted in 2011 (not to mention a few scars).

The cover letter:


In the past two years, technology has gone through a massive upheaval due to three disruptive innovations that can’t be ignored: the iPhone, Cloud Computing and the “Consumerization” of IT. Each individually changed the rules of the game.

Taken as a whole, this triumvirate has changed every business user’s expectations about how products should work. IT departments have to build API-based applications that work as well on mobile devices as they on a desktop. These applications must strike the balance of simplicity and power already available to users through services like Gmail.

I want to work for an organization who knows that, in order to succeed, it must embrace this change that mobile and cloud platforms have enabled. I maintain a steady diet of RSS feeds, newspapers, books and podcasts in my unending journey to perfect my craft. With this knowledge, I explore and build web applications and iOS apps using the latest offerings from Google, Amazon Web Services and RackSpace.

I believe in the following tenets for product design and development:

  • App Store craze aside, HTML5-based Web Applications are the present and the future
  • If a new application doesn’t have an API, it wasn’t built correctly
  • If a new application isn’t SaaS-based, a business opportunity is being missed
  • If a user needs to be trained to use an application, it hasn’t been designed correctly
  • If you don’t embrace all that open-source has to offer, your competitor will
  • Design is everything; you have to sweat the details to make great products great
  • If you want to innovate, you must embrace both failure and the unorthodox

This is a very exciting time for technology and I’ve never been more motivated to be a part of it. I’ve spent the last 8 years navigating the challenges and politics of life in the corporate IT landscape, but I’m now looking for a company that shares my entrepreneurial spirit and passion for creating exceptional products.

I feel I have a great deal to offer, and if you see potential in me, I look forward to speaking with you.

Thank you, Jeff Devine