How to get replies by cold-emailing busy people

Over my career, but especially last year while working on Housecraft, I've used the tactics below to get responses from the CEOs of Redfin, Wayfair, Enjoy (Ron Johnson; he created Apple stores), Twilio (my first job), and a lot more. Later in this post I'll share the exact (somewhat embarrassing) emails I sent each of them.

The keys to e-mailing a CEO are:
  1. Get their attention
  2. Say why you're emailing
  3. Present an ask that they can act on in less than 15 seconds

1. Get their attention

The key to any good conversation is this: make it about the other person.

You don't walk up to someone and start telling them about yourself. A good conversation involves you being genuinely curious about another person.

So how do you make an email to a CEO about them? Their job means they're heavily focused on telling and spreading the story of the company. Luckily for you, talking about that story is relatively easy!

What I've often done is read blog posts or listen to podcast interviews with folks I'm trying to contact. This helps me understand where they're coming from, and where their company is going. It's also fun and shows your genuine interest in the company (and if you don't find it interesting, maybe you're in the wrong biz).

Your subject line should specifically mention the blog post, interview, or article. Specifics always capture attention. Then inside the e-mail describe something you learned or connected with in 2-3 lines.

2. Say why you're emailing

This is the least critical part of the e-mail.

Mention your own product in 1-2 lines in a new paragraph. Make sure it actually is something they should care about. If it isn't, you'll feel crappy and will definitely never hear back. Your goal is to give them context for the next section: your ask.

3. Ask for something they can act on in less than 15 seconds

Imagine you're running a company with hundreds or thousands of employees and you get two cold-emails. Each ends with one of these lines:

- "Do you have time this week for a quick call to talk about [insert my product you don't care about yet]?"
- "Can you direct me to your product manager in charge of mobile?"

The second option is something they can act on quickly, which moves the email out of their inbox and off their plate.

CEOs are Grand Central Station, and a large part of their job is directing resources, whether it's emails or capital. People in their situation appreciate when people are 1) direct and 2) ask for simple things. Make it easy for them to do their job.

But what if you don't know what to ask for? Often the best move is to let the CEO tell you who you're looking for.

Say, for example, you're selling software to help them better measure important data in their mobile app. Don't guess that you should be talking to the Mobile Project Manager. They might not even have one! Instead, ask: "Can you direct me to the person who deals with data analysis of your app usage?"

That's it!

Beyond that, if you want to really up your odds of a response, you should email around 9pm in the evening (their time), very early on a weekday, or on a Sunday late-afternoon. Busy people like CEOs and investors are often in meetings much of the workday, so they clear out their email in the margins of the day. I've noticed many hop on Sunday evening to prepare for the week.

Read below for some examples of how I've successfully put this into practice.

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Real world examples

Glenn Kelman – Redfin CEO
At one point I decided Housecraft would do well to partner with a real estate company, especially since so many realtors use our product. I didn't know where to start inside Redfin, so I decided to email the CEO about a great blog post he wrote. He really appreciated it and connected me with exactly the team I needed to talk to.

Successful email to Glenn

Want proof that the first email worked and Glenn isn't just a nice guy (though he is!)? Four months earlier I sent this email and never received a response. Things I did wrong? Subject line was clearly a pitch, focused on my product, and there was little reason inside for him to read my dense email.

Failed email to Glenn

Niraj Shah – Wayfair CEO
Similar to the Redfin example, I listened to a podcast episode with the founders of Wayfair. I really connected with some of their early experiences, and wanted to share that with him. Since they'd been talking about augmented reality in the press, I knew he might be interested in Housecraft.

Successful email to Niraj

The success above was preceded by this failure. 20 days earlier I'd sent both founders an email with a follow-up later that week. Total silence.

And it's okay if they don't respond right away. It just might not be the right time for them. Often you'll get through on the 3rd or 4th email, just be sure you focus on what they care about. This email didn't do that:

Failed email to Niraj

Ron Johnson – Enjoy CEO / Creator of the Apple Stores
Having figured out what works, I've been making sure my first email is always focused on them and not on me. It's been going a lot better.

Ron was a VP at Target, then he joined Apple to create the Apple Stores, and now he's running a startup which helps people buy and setup electronics and home goods. I didn't have a clear need or ask from him, just wanted a conversation or advice. Instead of asking directly for his time, I focused instead on a related Yes/No question. This gave us a starting point to have a real conversation and for me to get the advice I needed.

Successful email to Ron


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