How To Write Original, Personalized Cold Emails at Scale

non-spammy, non-awkward ways to email like a pro

Efficiently reaching out to potential employees, companies, or really whoever is its own quirky art — one that I happen to love. After a few recent email requests, I’ve decided to start a Medium Collection called Ice Breaking: mastering the cold email, and other web interactions that need warming up.

In this collection I’ll try to shine a light on non-spammy, non-awkward ways to communicate with lots of new people at the same time.

Cold Emailing 101: Be Prepared

There are a few tough parts to delivering a killer cold email. You need to be cool, but you also need to do your homework. You need to be diligent — sometimes who you’re emailing forgets to respond, or the thread just get lost, or just gets caught up in life, but is interested — and you need to be super open to the thread’s direction.

I think the most useful cold emailing tip I can offer is to be prepared. Save yourself time by setting up your tools, so you can take advantage of life’s serendipity instead of letting it fly by.

Here are a few of my favorite hacks for sane, productive, creative cold emailing:

1. Text Expanders

Text expanders are basically hot keys with pre-written text. You can use them to craft parts of messages, and then weave them together to make the experience custom to the person you’re emailing. In the past I used Text Expander, but now I use Streak’s in-email Snippets. I have probably 50-60 different messages that I try right now, and label with semicolons (ex: ;iOS7 or ;intern-faq or ;addr).

If you write a lot of emails and have a tendency towards automated/efficient solutions, these can be a lifesaver. (note: using them to copy complete messages more or less a waste, since messages tend to look pasted.) It’s important to remember that your scripts are never done. I reread and rewrite mine pretty frequently, edit the copy and positioning constantly, and delete ones that are no longer applicable. I also like to create a few different variations, and then delete the ones I use least.

2. Email Tools

Though I wouldn’t say any of these products make the content of my emails more engaging, they help me keep my sanity, which has to count for something.

I use Rapportive and Pipeline for all pre-email due diligence. I start with Pipeline to save a person’s contact info, and then double-check it with Rapportive. I then use Streak to track that email by candidate name, and to input any extra info I remember about that person. I also use it to remember the people I actually talk to, because otherwise threads get lost.

3. Gifs

I use the Giphy Chrome Extension religiously (in fact, it was my early Giphy feature request!). I mostly pepper my semi-scripted emails with relevant jokes and visuals that tend to, well, break the ice — but I also sometimes use it instead of text to lighten the awkwardness of a conversation. More on these in future posts.

Giphy tag suggestions: Boom, What’s Up, Awkward, and all the Reaction Gifs.

I’ll be doing a deeper dive on specific tactics over the next couple weeks, but feel free to email me if you have any specific questions. Or, if you want to receive personalized job recommendations from me, Sign up here.