Lost Deal Drip Email Campaigns

Photo by Joshua Ness on Unsplash
Photo by Joshua Ness on Unsplash

Sales is a challenge for many of us. It is the lifeblood of our business so we spend a lot time and resources on it. But the unfortunate reality is that most leads do not turn into customers. There are many reasons for this including they might be just window shopping and gathering information, they aren’t ready to buy, they use one of our competitors, or our product or service is not a good fit.

Behind all of those is a time component. Those all might be true right now but might not be true in the future after you have improved their product, your competitor has stumbled or not lived up to expectations, or they have moved forward in the buying process. A “no” now can turn into a “yes” later.

I saw this post from Jason Lemkin of SaaStr about drip marketing campaigns for lost deals and thought I would create a few email templates for you to use based on his suggestions.

10 months out (Renewal #1). If your competitor really screwed it up.

You’re hopefully rolling out new features or services at least every ten months and this email will bring attention to that. At the same time ten months is too soon to do another hard sell so this email just tries to sell the lead on a quick chat to catch up and find out how things are going.

{{ subscriber.first_name }},

I wanted to check in and see how things are going. We talked almost a year ago about <the problem> and you mentioned that you are using {{ subscriber.current_provider }}. How is that going?

We’ve rolled out some new features <or services> but are also continually looking to improve so learning a bit about what is working with {{ subscriber.current_provider }} and what, if any, difficulties you might be having would be very helpful for me.

Do you have five minutes later this week for a quick call?

Wed @ 9 am {{ subscriber.friendly_time_zone }}
Thur @ 2:30 pm {{ subscriber.friendly_time_zone }}
Fri @ 9:30 am {{ subscriber.friendly_time_zone }}


{{ from_name }}

20 months out (Renewal #2). If your competitor doesn’t remain competitive and deliver enough value.

At this point your business has hopefully matured and your product or service has improved significantly while at the same time your competitors might be big enough that they are not innovating at a quick pace or are slow to respond to customer concerns.

{{ subscriber.first_name }},

I hope you are having a great week.

You have been using {{ subscriber.current_provider }} for a while now and I wanted to check to make sure that is still going well for you. We have been aggressively adding new features <or services> that have been providing a lot of value to our customers and I think we’re very competitive with {{ subscriber.current_provider }}.

I would love to have a quick chat with you to see if we can deliver a higher value to you today than when we last talked and make <the problem> a thing of the past.

I hope business is going well and look forward with connecting with you soon.

Have a great day,

{{ from_name }}

30 months out (Renewal #3). If your competitor did an OK job but isn’t loved and you now are doing something much better (one thing) than them.

As a business grows its needs change and the reasons for picking a solution in the past might no longer be valid. While your competitor might have been a better solution three years ago you might better address the pain points the customer is having now.

{{ subscriber.first_name }},

I wanted to check in and see how {{ subscriber.current_provider }} is working out for you. Since we first spoke a few years ago we have been investing a lot in improving our service and, due to those improvements, a lot of businesses are finding that we are a better fit for them now.

If you’re really happy with {{ subscriber.current_provider }} then great. If not, I would love to talk with you for a few minutes to see if we might be a better solution for you today.


{{ from_name }}

Implementation in Drip

Create the “Lost Deal Campaign” with these three emails.

Lost deal drip email campaign

(If you use a CRM system to track emails you have sent to your leads set the campaign up to automatically BCC yourself on each email so that it will be picked up by your CRM.)

Create a new workflow:

Lost deal workflow in Drip
  • Start workflow then the tag “not_interested” is applied.
  • If the subscriber has a custom field set with the current provider (the emails you created reference that so you don’t want to send them without that information) then send campaign otherwise exit workflow.
  • Wait ten months to start the email campaign
  • Create a goal (“customer” tag applied) so that if that happens the subscriber is pulled from the “Lost Deal Campaign” and not sent anymore of those emails.
  • I have a separate workflow (“Customer Onboarding”) which is triggered when the “customer” tag is applied.

One obvious improvement is to add a campaign that doesn’t reference the current provider so that all lost deals get follow up even if you didn’t get the information about which of your competitors they use.

When creating a subscriber in Drip (Import/Bulk Ops -> New Bulk Operation -> Enter a list of email addresses) you have to create them using an email address and then you can go in and update their fields. Be sure to set the “current_provider” customer field prior to adding the “not_interested” tag.

Close.io to Drip

If you’re using CRM software then you probably would prefer to automate this whole process–more time for sales! You can do that using Zapier so that when you mark a lead as “Not Interested” in your CRM (or opportunity as ‘Closed: Lost’) it will automatically create a subscriber in Drip, set their current provider, apply the ‘not_interested’ tag, and start sending them the email campaign in 300 days.

I use Close.io and this is the zap I created for this:

Lost deal email Zap with Close.io and Drip

The Close.io trigger:

Close.io trigger in Zapier

The filter for only status changes to ‘Not Interested’:

Zapier filter for lost deals

Setting up the contact in Drip:

Adding contact to Drip in Zapier

(edit: If you use Zapier to create subscribers from Close.io contacts then you don’t currently get separate fields for first and last name but rather a full name field. You can use the following in your Drip emails in order to address your emails to someone’s first name: “{{ subscriber.name | split: ‘ ‘ | first | capitalize }}”. Thanks to Andy at Drip for that.)

“No” means “not right now”

You put a lot of work into turning leads into customers. Don’t let the “no” be the end of your relationship. By using this lost deal drip email campaign you turn that “no” into just one step of a much longer relationship. One that hopefully includes them becoming a customer at a later date.