TL;DR: Send an email that expresses excitement about the business and alignment with the job description, and offer to grab a coffee.
Cover letters have always felt out of place in the context of startups. Larger companies filter heavily on applications, but startups are generally willing to do a phone screen and assign some work. Still, cover letters do serve a purpose, and it is something like the glue between the job and the resume. For better or worse, that glue can make all the difference in getting to the next step, because it’s a big part of your first impression.
It’s important to get first impressions right, and initial communications with a company about a job are no exception. The industry wants you to think that this first communication has to happen in a cover letter that you attach to a job application, but that’s not true. Rather than constraining yourself to a web form, take control of the first impression you’re going to make.
The nice thing about startups is that they often provide a public-facing email address. Whether it’s the CEO or a generic address, using email for the first encounter allows you to maintain control over the communication and get direct access to a person’s inbox. If the company doesn’t advertise an email address, you can use a free EC2 instance to get around residential IP address blocking, then find their mail servers with nslookup and connect to their mail server with telnet to check for valid email addresses on their domain.
Once you know where to send your email, draft it. If you’re not sure how to structure it, check out our Cover Letter Guide on Tailspin; we provide two, simple templates for initial job inquiry emails that have successfully converted into in-person interviews.
Last but not least: Good luck!
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