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Freelance Sales 101: The Follow Up Gets the Sale

Freelance Sales 101: The Follow Up Gets the Sale

Maddy Osman

By Maddy Osman on Apr 24, 2018

CRMs aside, there are so many other sales tools that freelancers can take advantage of to close more deals and make more money.

Cirrus Insight has a Google Chrome extension that empowers salespeople to be more productive from within their inbox—eliminating manual data entry to Salesforce.

When Cirrus Insight released a standalone version of their product—one that worked within Gmail without needing a Salesforce integration—they effectively created a new user base for their products: freelancers.

That’s not to say that freelancers don’t ever use Salesforce. As someone whose post-college career involved sales, I got very comfortable with the platform in my first sales job.

But with so many free customer relationship management (CRM) tools available, it seemed silly for me to be paying more for something involving a lot of functionalities I honestly don’t really need.

Cirrus Insight can help freelancers and small business owners get intel on how prospects are interacting with your emails, if they’ve viewed proposals and other attachments, as well as offering meeting scheduling tools that eliminate the annoying back and forth that usually comes with finding a time to chat.

Today, we’ll focus specifically on how freelancers can use Cirrus Insight’s Flight Plans feature to advance the sale.

The Sale is in the Follow Up

Salesforce reports that it takes 6 to 8 touches to generate a viable sales lead.

For those with a full-time corporate job, your company probably takes care of a lot of these “touches” in terms of targeted marketing efforts: social media advertising, emails, and so on. For a freelancer, you don’t necessarily have a marketing department to assist you—you wear all the hats when it comes to business development!


Image Source

If we are to believe the numbers on this widely-shared graphic, most closed won sales (80% of them) happen during the fifth to twelfth contact. The chances of closing a prospect outside of that range are hardly worth considering. Why hurt your own effectiveness by failing to implement a basic follow up strategy?

Besides investing in expensive software tools with a huge learning curve (and a lot of features you might not even need), it’s much less of a hassle to use tools that fit within your existing workflow.

With this in mind, to help freelancers implement their own effective sales follow up strategy, consider Cirrus Insight’s email drip campaign feature—also known as “Flight Plans”.

The Basics of How to Set up a Flight Plan

  1. Sign up for Cirrus Insight

There’s a free 14-day trial available, so you can test it out before committing to it. Once you download the extension from the Chrome store, then activate it in Gmail, you’ll be ready to get started!

2. Plan Your Follow Up Strategy

If you haven’t developed your own sales process yet, you might be feeling a bit overwhelmed by the project. One of the benefits of using Flight Plans is that the process to set them up helps you to more easily structure your personal sales process.

For the purposes of setting up your first Flight Plan, ask yourself questions like:

  • How do I pitch and position myself to new customers? What do I say in that initial communication after connecting (or as a first connection)?
  • How many calls/emails are necessary to get from an initial consultation, to a proposal, then to a signed contract?
  • What language should accompany sending certain documents?

3. Set up Your First Flight Plan

Like an email drip campaign a marketer might send out, Flight Plans allow you to create a templated response to various situations, with areas that can be personalized for each client. By using email templates, you’ll spend less time on prospecting and more time on the business activities that actually make you money.

Flight Plans work with this concept in mind. Using merge tags, you’ll be able to format each individual follow up according to the contact information you have.

Before sending out any Flight Plan, you’ll have to enter in relevant prospect data—which could be as simple as an email address or as complicated as a database of contact information like what you’d find in Salesforce.

To add the contact information, you’ll be prompted to add in data via CSV upload or manual entry:


Whether or not you’ve uploaded prospect contact information at this point, you can start creating your first Flight Plan.

Go to the Flight Plans tab in Gmail > Flights > Start a Flight.


Next, you’ll be given the option to create one or multiple steps within your Flight Plan. Each step is associated with a certain action: an email to be sent, a book meeting request, a call to be made, or a task to be completed.


For my first Flight Plan, I thought it would be useful to create a process around connecting with the people I meet at networking events.

Here’s how that basic email template turned out:


Note that if you’re using merge tags, you’ll want to make sure that you’ve uploaded relevant contact information for each field—or make sure that you don’t check the “Send email automatically” checkbox so that you can add this information in yourself before sending.

After this first touch, I’ve created two additional steps for this Flight Plan.

  • An invite to sign up for my email newsletter, where I can indirectly “sell” to prospects by showing off client work:


  • A meeting request to chat about content marketing needs:

Since the meeting request is the last step in the Flight Plan, you’ll notice a “Choose Outcome” call to action.

Outcomes in Flight Plans can refer to negative or positive results. If someone takes an action that you’ve designated as “positive”, you’re telling the system that the sale is advancing. A “negative” outcome, such as an individual Flight that fails to return any response, means that the sale isn’t going anywhere.

When defining your own Outcomes, consider the descriptor as the end goal of the Flight Plan. In this case, it’s to get the meeting booked.

Outcomes also ask you to designate a goal value, or the monetary impact of your activity. For this Flight Plan, I have to consider what a booked meeting is worth to me—as well as the impact of spending time on an unresponsive lead!

Don’t worry about being specific if you’ve just started developing your sales process. Once you gather more data, you can go back in and refine your goal values.

Once you’ve set up your first Flight Plan, you’re ready to start sending it to a list of prospects. Check out Cirrus Insight Academy for more specifics on Flight Plans best practices and follow up activities.

Final Thoughts: Freelance Sales 101: The Follow Up Gets the Sale

With a little work on the front-end, creating a Flight Plan for different types of prospects and situations, you can automate a lot of your follow up sales activities. Putting in the effort up front will pay off in the long-term, as you build relationships with prospects that lead to closed won sales.

Having other issues with sales as a freelancer? Check out my Skillshare class, “How to Negotiate a Six-Figure Freelance Salary”. Specific questions? Tweet @CirrusInsight and we’ll share the best questions—alongside the advice of our sales experts on staff!

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