Three Laws of Cold Emails


This year, I’m going to start cold emailing customers.

Every VC and growth guru will tell you to do drip campaigns (as growth engineer, I’ve heard the whispers for two years). But I know, despite its efficacy, what drip marketing feels like as a recipient, and I’m hoping we might be better.

We as an industry are so anxious to hit “scale” that we sometimes rush past the question What are you scaling? If your email is mildly useful to the 5% that clicked through, mildly annoying to the 90% that did nothing, and irritating to the 5% that unsubscribed, why are you so eager to reach bigger audiences? Are you just muliplying a slight negative?

“Build something people want.” Why shouldn’t this apply to not only writing code, but also writing emails? It shouldn’t be hard: humans love to communicate with each other. Yet, 99% of the emails in my inbox aren’t communication. They’re blaring broadcasts from noreply addresses. They aren’t for communication, but to “drive behavior.”

Tell me I’m naive or worse yet, over-thinking the problem (“Wait until someone is mad. Then fix it.”). But as I tell new hires, “When you’re new, you have a rare perspective. Only the naive can call out the Emporer’s new clothes.” I’m going to let myself go with it and do things a little differently by laying down three laws that

1. From my email.

I won’t be using a marketing automation tool.1 I’ll be typing in Gmail, sending from my work email. After all, you’ve given me your email, it feels fair you should have mine. Yes, I’ll be copy pasting snippets, but I won’t be using fill-in-the-blank campaign template.

So when you reply back with all caps “UNSUBSCRIBE”, I’ll see it personally, not just in my end of quarter internal metrics. Take my email and put it in the last most-annoying drip campaign. Or worse yet, mark as spam, the silent killer.

“But how will you scale?” These days, scale is trivial. If you have a motivated engineer, figuring out how to organize information is just an API away. I’ve already begun work on a Gmail-to-Postgres app that allows teams to share and analyze their Gmail outreach with SQL.

2. State my reason.

Anytime I email a customer, I should clearly state why. After all, “Why are you emailing me?” is exactly what I ask whenever I open most emails. If I am going to intrude on your inbox, it should be not only obvious why, but also directly related to your goals, not mine.

Some examples:

  • You’ve recently setup (or tried to setup) a new feature
  • Billing oddities and notifications
  • On behalf of shared colleague (finance team members)

Some anti-examples:

  • End of the year sale!
  • Our internal targets aim for X level of activation by Y day…
  • Another customer just told me he really likes us.

3. Measure relationships, not revenue.

In organizations, feedback loops are everything. Metrics incentivize behavior and structure departments.

I’m going to measure myself entirely on reply rates. That means if you don’t do anything, you’ve contributed to a negative feedback loop. There are no revenue expectations. If I talk to 100 users, and it turns out the exact same number convert at the exact same ratios to our small, medium, and large plans, that’s on Sentry. It means the product or the plans need to be fixed. Consider your cold emails as a product in and of themselves. You’re looking to build relationships like a product looks to engage users.

Finally, there is a risk that my laws aren’t practical. If I’m not “selling”, then…how can you justify the time/headcount? I believe that revenue follows value. If you start with the belief that Sentry is a great product that provides real value to its users, my part is to make it easier to use. My emails are explicitly meant not drive sales so ensure the quality of the emails themselves. We, of course, will measure the economics of these emails, and I’ll report back on whether my three laws are worth following.

  1. Unsubscribe rates are such a low bar when you hide the unsubscribe link. If you send 100,000 emails and only 5% click through, that means potentially you’ve wasted a few seconds of 95,000 people’s day. Broadcast seems cheap until everyone’s shouting at the top of their lungs.