Streak for GMail

streak gmail crm

I wanted to finish up the week of picks with something that covers one of the most frustrating topics I can think 20+ years after getting my first email address and I still haven't figured out the perfect system. The part of me that grew up with apps like Eudora and Outlook longs for the folder structure and advanced features of a desktop app. The part of me that has been using iPhones, OSX, and Chrome for the past several years prefers the ubiquity of GMail's web client. It seems to be a constant arms race to see which side will win my attention, so anytime I find a utility that makes this part of my workload easier it gets my full attention.

Today my pick is Streak for GMail. The truly ridiculous part of this pick is the fact that I'm only using one or two of the features available...and not even the main features. I think this is an add-on I'd like to do a full post on in the future. For now I'd just like to tell you about the features I'm using.

Streak is a full (free) CRM solution that plugs right into GMail. Once installed you can setup departments, projects, and stages to track any actionable email that shows up in your inbox. This can be really powerful. You can setup different departments (sales, marketing, support) that get shared with different members of your team. If most of your new tasks first show up in email, and you want to keep your task management right inside GMail, this is a great system. I've used Streak's full set of features on a few occasions, and it's very easy to use. I'm a diehard OmniFocus user though, so I don't really have the need for a separate task management system.

The first feature I use quite a lot is "Send Later".


There are a few reasons you'd want to use this. If you do a lot of late night work like I do, you might end up sending a lot of emails to clients or colleagues at 1:00am. This is usually not an issue...but there's always a chance you're sending one of these to someone who forgot to mute their phone. Suddenly they're getting a loud email notification on the phone 3 feet from their head while they're trying to sleep. Ok, probably not usually an issue, but "send later" will let you schedule all of these late night emails for 8:00am.

The biggest way I use this is as a reminder to my future self. I'll email myself something like "check to see if customer x's payment showed up" and schedule it for next week. A week later I'll have a new email in my inbox with the helpful reminder.

Earlier this year Streak added a new feature that really got my attention.



Email snooze lets you send an email out of your inbox, only to have it reappear at a later date. The one handy additional setting here is the checkbox "Only if no one replies". I use this in one of two ways.

First, if I send an email to someone where I am expecting a response, I will snooze this for x days and check the box. If they reply before x days I can follow up and the email won't show up again to remind me. However, if I don't get a response, the email will reappear in my inbox to remind me to check back with the recipient.

Second, I will snooze an email I receive if I don't have time to properly deal with it in the moment. Like, for example, this email in the screenshot I got from Dropbox informing me they lost some of my files (oops). I need to figure out if/where my other backups are before I completely freak out, so I'm going to have this pop back to the top of my inbox tomorrow.

Sometimes I want to clean up my inbox so all that remains are the things I can deal with today. Other times I'm waiting for additional information before I can respond so I'll push it out a day or two. That way it shows up at the top of my inbox at a later date, and avoids getting buried at the bottom of the pile.


There are 2 other services that I've used in the past for this.

NudgeMail - This one is not only free, but dead simple to use. Let's say you want to remind yourself of something on Monday. Here's what you do.

To: Subject: Don't forget to do xyz. SEND

Yep, that's it. You can also send the email to and use Monday as the subject. Either way on Monday you'll get back the contents of the email. The one limitation here is that it doesn't support attachments. If, for some reason, you really need to have an attachment here I'd suggest including a link to a file stored in Dropbox or Google Drive instead.

Boomerang - Boomerang is another GMail add-on with similar features. It adds a button to your GMail UI, similar to how Streak does. It's free for up to 10 uses per month. If you want to use it more often there are paid tiers. Personal is $4.99/m and gives you unlimited uses with an address. If, like me, you have GMail setup with your domain, Pro is $14.99/m...which also gives you recurring reminders. There's a $49.99/m plan too but that seems crazy for a GMail add-on, no matter what features they include.


Eric Matthews

I'm a bookkeeper, husband, dad, music junkie, and general tech geek. When I'm a bookkeeper, I focus on cloud bookkeeping. I write at, which helps bookkeepers and business owners move their books online. I work with apps like FreshBooks, Xero, Kashoo, Wave, and QuickBooks Online.

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