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How to Save Your Sanity With Streak and Gmail

I've know Clara for a little bit now. She has here own freelance writing business and produces some ridiculously good content you can check her out at her site Today she is going to help you revolutionize your email strategy to help you find more clients faster without going crazy. Enter Clara


You learned about being a freelance writer, either through this blog or by reading Josh’s wonderful book on freelance writing on the side. Good for you! So what’s next?

The first thing you need to do after getting your portfolio pieces ready is to collect leads. Lots of them. You’ll email SEO companies and other businesses constantly. Your leads are the lifeblood of your freelance business.​

Josh recommends emailing 100 businesses per week. Do this consistently and you should be able to get writing jobs sooner or later.

But there is one problem. Exactly how do you keep track of everything you do, from collecting email addresses, sending out emails, remembering who to follow up, etc.?

Most people start out with Excel or Google Sheets, but once you get into hundreds of leads, you need something more robust.

Salespeople use CRM (customer relationship management) software. You’ve probably heard of Salesforce. Starting out though, you might want something free, easy to use, and less intimidating.

If you’re using Gmail, which is more “acceptable” for business than Yahoo or Hotmail, look no further.

Enter Streak.

Streak & Gmail

Streak is a free (upgradeable to paid) Gmail add-on. It simply works as a part of your Gmail inbox and helps you keep track of all of your leads in a CRM-like environment.

Speaking of Gmail, sign up for it if you don’t have a website with your own domain name yet. And if you already do, you can have your forwarded to a Gmail address.

The chances are, Gmail is infinitely superior to an email service from your web host. Get a Gmail account strictly for business so you don’t mix up personal emails with your business ones.

Streak has a lot of functionalities, but the ones you’ll want to get familiar with as a freelance writer are lead management (known as “pipelines”), mail merge and email tracking features.

When you download Streak, it’ll install on your browser as an extension. I use Safari but you can use any other browser.

Follow the instructions and restart Gmail. Streak takes a few seconds to load each time. You’ll see this initial popup screen. Choose Sales/CRM since that’s what this post will focus on.

You’ll have to click through a couple more steps, but after you do, you should be able to see the icon for Streak in the upper right-hand corner, and your Pipelines in the sidebar.

Pipelines let you organize your leads into different groups. When you choose Sales/CRM on the initial screen, that’s what will show up under your Pipelines.

Per the example on the right.

Customizing Your Streak Interface

When you click on the Sales/CRM pipeline, you’ll see different “stages” for your leads (Lead->Contacted->Pitched->Demo->Negotiating->Closed-Lost->Closed-Won). The stages are self-explanatory and you can easily visualize the cycle of your leads.

You can rename or delete any of the stages to your liking. I find the default stages closely resemble my process, so I generally keep everything except the “demo” stage. You can rename or delete stages by hovering over each of them and clicking on the icon in the upper right corner.

I do like to customize the column headers. The default column headers are Name, Stage, Deal Size, Assigned To, and Notes. I leave in Name, Stage, and Notes, and delete Deal Size and Assigned To.

Then I create new columns for Email, Phone and Website. I do this through Free Form and manually type in the new column names.

You can move the columns to left or right from the dropdown menu next to each column name. I like to have my columns in a specific order. This is what it looks like after I’ve rearranged everything.

Importing Your Leads

Now it’s time to import your leads. You can create leads directly in Streak, but I find the process cumbersome. If you do decide you want to insert leads inside Streak, you can go to “New Box” and manually enter in all the information.

Like what you've seen so far? Why not stop and share?

In Streak lingo, “Box” refers to everything pertinent to a lead, whether it’s a person or an organization. You can see all the info related to a lead by clicking on the box icon.

Personally, I like to work in a spreadsheet when collecting leads, because it’s easy to toggle back and forth with a browser. I can also tab between columns faster.

You can use Excel (my choice), Google Sheets, or any other spreadsheet you’re familiar with. The only requirements are that your column names match what you have in Streak and you save your spreadsheet as a .CSV file.

You don’t have to have the “Stage” column in your spreadsheet, but if you want all of your other columns imported into Streak, you need to have them in your spreadsheet as well.

Once you save your spreadsheet as a .CSV file, import it into Streak from More->Import Boxes from CSV.

You’ll see a popup screen that tells you how many leads (boxes) and matching columns Streak wants to import. After you’re done importing, you’ll get an email from Streak saying the import process was successful.

Unless you specified “Stage” in your own spreadsheet, all new leads will be imported under the “Lead” stage.

Mail Merge

After you’re done importing your leads into Streak, it’s time to send out some emails. You can send them all of them at once or just a few at a time. The real power of Streak is its mail merge feature.

The important thing when sending emails is you want to customize each email a little bit. If you send out emails that are too similar in content successively, Gmail might think you’re spamming and prevent you from sending them out.

The “Notes” column in my spreadsheet is where I keep unique information about each lead so I can quickly reference it to customize my emails.

Check the boxes next to the leads you want to email, then go to More->Send Mass Email (Mail Merge).

The important thing when sending emails is you want to customize each email a little bit.

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If you’re using Mail Merge for the first time, you’ll be asked to turn on email tracking by default. Since this is your “business” email account, you should leave it on all the time so you can track all your emails.

After mail merge, you’ll have a popup where you can start writing your emails. When you make changes to the right panel, they will apply to all the emails. If you want to customize each email with different pieces of information, you have to click the “Edit” link under each email address in the left panel.


Of course, it’s tedious to copy and paste subject line and body into each email. That’s why Streak has an awesome feature called “Snippets.” They’re pre-made blocks of text that you create once and reuse over and over. You can create as many snippets as you need.

Creating new snippet:

The shortcut will come in handy when you have multiple snippets and need to find them quickly. I preface my shortcuts with an exclamation point for organization.

Using the snippet you just made:

All your emails will have the same subject line and body from the snippet:


You can further customize each email by using templates. Not to be confused with snippets, templates allow you to automatically populate certain data from your leads.

If you can manage to get your lead’s first name (for SEO companies, I often have a hard time with this), this is a great way to customize your email so it starts with Hi First_Name.

For this example, I’ll customize each greeting with “Hi Name” just to show you how you can use templates.

After customizing each greeting with the name of each lead:

As you move down each email, you can see how the greeting changes with the lead’s name:

You can use templates in your subject line as well.

Schedule Emails

It’s a good idea to schedule emails to send later. You can test different times to see which time gets more open rate.

Josh recommends not sending any emails on Fridays or weekends. People get antsy and distracted on Fridays, and emails sent on weekends are likely deleted on Mondays when people get in the office.

So schedule your emails to be sent from Monday through Thursday at the time of your choosing.

Streak automatically keeps track of all email correspondences tied to each lead. Just click on the box icon next to each lead and see all the corresponding emails.

The box for Jane Doe:

After Sending Your Emails

After your emails are sent, you should do one of two things. Move all your leads (that you sent emails to) to “Contacted” by double-clicking in the “Lead” field. You’ll repeat this process as you get responses and move your leads through different stages of your outreach.

You can also check which emails were actually viewed. To do so, go to Sent Mail->All Tracked Emails. The “eye” icon is gray by default, and should turn green if someone opened your email.

Tracking your emails helps formulate your follow-up strategy. Keep in mind that it doesn’t tell you whether someone’s deleted your email (as sad as it is when that happens).

If 7 out of 10 people are opening your emails but none are responding, you can deduce your subject line is okay but your body copy might need work. This type of data can yield some powerful results as you continue to tweak your emails.

This type of data can yield some powerful results as you continue to tweak your emails.

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Final Thoughts

Streak has incredibly powerful features as a free app that there is almost no need to upgrade to paid versions. The $39/month corporate plan is useful if you have multiple members on your team and want some reporting features.

This post barely scrapes all the things Streak can do, but it’s enough to get you started. Take your time to read all the tutorials and click around on your own.

More importantly, get started on sending those emails!

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