Creating a great email subject line

We can likely all agree we don’t need yet another email, but if you’re like me, I appreciate a thoughtful email. The problem is a clear email message with a bad subject line doesn’t even get opened. Having worked with many SaaS companies across multiple industries, we have found there are three tenants of a good subject line.


To grab someone’s attention you can’t talk about yourself. A common mistake is to send an email saying… “Dropbox for Business can help your Teams”. Even if you are as well known as Dropbox, you’ll get better results by speaking directly to THEIR benefit. If I were Dropbox, I’d write “Sharing files with team members just got easy”.

If you struggle with not talking about yourself, then focus on either the prospects’ pain point or opportunities for them to gain something from using your software. Your subject line can be about avoiding the pain your prospect incurs or identifying the gain they could have.


You obviously don’t want to be boring, and humor can be a powerful tool, but it’s difficult with email. Being clever is less risky than trying to be funny. However, the strategy that works better than both, with very low risk, is to create curiosity.
Remember, the goal of the subject line is to get the email opened. An easy way to make someone curious is to ask them a question, uncover a secret they haven’t seen, or connect your message to a popular topic.


Good marketing, as we discussed last month, starts with defining your segments. A few great ways to personalize your message is to do your research and find a common interest, a similar city to a current customer or a place you’ve visited and finally, reference their alma mater. I avoid the tactic of assumption and just prefer to spend more time researching a strong connection point.

Recently I ran into a Fintech CEO who knows me through an angel investor who invested in each of our companies. We ran into each other at a conference in SF and a few weeks later again in a hotel lobby in Atlanta. We both laughed about it, so a month later I sent him this email subject line: Missed you in San Diego.

I knew we could help his business grow, but I didn’t see the need to be pushy. He replied and said… “Hey man! That’s hysterical — you never know where we might run into each other next!”

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