What's in this article?

Getting into Your Customer’s Head
Designing an Email Sequence
Writing Subject Lines
Writing Emails the Get Replies and Clicks
Example Drip Emails

Writing is an essential skill for marketers and sales people. Learning to write emails that consistently convert is a superpower.

Knowing how to write drip email campaigns that add value, build trust, and make people eager to buy from me has allowed me to:

  • Grow and sell a couple of businesses,
  • Weather crisis and pivots, and
  • Live a life that focuses on family and working with and for good people and not having to endure the grind to get paid.

Ultimately, that’s what this article and this webinar is about. Teaching you my secret weapon and insurance policy for all weather sales and marketing.

This is, by far, was one of my most popular webinars.

Writing emails that convert requires a process.

My framework breaks down into four phases:

  • Getting into my customer’s head
  • Designing my sequence, journey, lifecycle (there are lots of names)
  • Writing subject lines, lots of subject lines
  • Writing emails that encourage people to take the next step – convert.

Getting into Your Customer’s Head

There are a lot of critical steps in the email writing process, but this is one that often gets skipped. Fight the urge to just sit down and start pounding out emails. Instead, step back and formulate some clear pictures of the people you’re sending emails to.

customer-focused email writing process diagram

Start by asking yourself, “where did these emails come from?” Did they download something from your website, did they fill out a form on your website, did you buy them from an internet lead aggregator.

Then ask, “why did these people give their emails?” What were they hoping to get or achieve?

This is one we often forget the think about: “What happened after they gave their email up?” I a lot of cases, the answer is nothing. To often sales and marketing people get people to fill out forms and call them, but then they drop the ball in following up and helping the person.

Most of your email list will start from a point where the customer feels a little abandoned or frustrated by the response (or lack of) they got when they provided their email address.

Other times, these people simply stopped responding to you. That might have made you feel a little frustrated. You’re thinking, “they asked for help and now they won’t respond, what the heck?” I know this frustration. If you’re not careful, it can play out in your email campaigns. Instead, reframe your mindset and understand that they more than likely had something change or take priority over that need or want (your product) or they just became overwhelmed by the process. Most will come back given an empathetic approach.

All of these scenarios change how I approach starting a conversation with these people. That is what we’re trying to do with drip email campaigns – start a conversation, not make a sale…yet.

With all of these things in mind, I start to scribble down ideas of how I can re-enter that buying journey that the customer was on before I stopped communicating with them.

Designing an Email Sequence

I encourage starting with an outline in all writing processes.

When you’re writing email sequences it’s even more essential. Email sequences are stories (sales pitches) that you are telling across loosely connected individual bite-sized emails. If you don’t start with an outline your emails will be haphazard and unremarkable in the customer’s brain.

However, if you craft a nicely connected and coherent flow your customer might even eager anticipate your next email.

So, as you begin planning your email sequence start with an outline. In this outline make sure that you break your overall objective or goal into steps. Try to limit yourself to only accomplishing one step in the process per email. Don’t try to do everything in every email.

Walls of text and long checklists don’t convert.

On the flipside of that extreme, don’t waste an email. Every email should have an objective – a single call to action (CTA).

Writing Subject Lines

Writing subject lines (headlines in general) is the most important skill of a copywriter. It’s the only way that you get an at-bat with a customer. If you can’t capture their attention, the best products and services die in a quiet forest with no one around to hear the benefits.

The best way to become a master subject line writers is to write a ton of subject lines. Most won’t. Those of you that do will make a lot of money.

Don’t believe me? I wrote an email last week that yielded nearly $5,000 – one email. Note that it’s nearly as much as my PPC campaigns yielded in the same week.

I wrote five subject lines before I settled on the one I sent.

Having said that, there are a few shortcuts – rules of thumb – that I’ve gathered over the years to keep my emails opening consistently. Here they are:

  1. Write like a normal person
  2. Keep them short and simple (less than 30 characters)
  3. Don’t be too clever. Don’t oversell. Don’t try to trick people.
  4. Don’t forget the pre-header
  5. Don’t use camel case
  6. Minimize punctuation
  7. Write a lot of them
  8. Test them

Do I ever break the rule. Yes, but only when I have a specific tactic or strategy in mind that warrants it. Getting cutesy and clever with subject lines will typically get you in trouble.

Writing Emails the Get Replies and Clicks

Now we’re into the body of the emails. This is where the money is made.

I could easily have labeled this section: “How Email Campaigns Fail.” What I’m about to outline for you are all the reasons that most email campaigns fail to generate a positive ROI.

how to make emails convert process diagram

I might sound like a broken record, but it works – never write one of anything. Writing takes a certain rhythm and flow. Email is no exception. Never write just one email.

This applies to even your everyday emails. If I need something from someone I write the initial email and then immediately write my follow-up email and schedule it.

Sales folks, write this down on a sticky note and stick it on your monitor. I will not follow-up unless I automate. Too often we think we can remember to follow up with our prospects and customers – we won’t. So, automate it – write and schedule that follow-up email.

This is why we do drip email campaigns. This is also why working aged leads is so productive. You’re harvesting all of the customers that salespeople didn’t follow up with – because they didn’t automate.

The next critical component of emails that convert are writing sequences that represent steps in the journey to buying from you.

Jason Fried from Basecamp coveys the power of this understanding more succinctly than I could…

Next, as I’ve mentioned before, each email should have a single objective or goal that moves the sale forward. That should be represented with a single call to action. And, that CTA should be a button.

Buttons get clicked, links often don’t.

Finally, give them one additional, low commitment, engagement option. Typically, I use some content or reference that services to build a case (value first) for my primary offer.

In presenting this low commitment engagement option, I love to use the power of the P.S. The postscript is one of the unsung heroes of professional email marketers. They have been some of my highest converting CTAs.

I highly encourage you to give them a try. This is a great place to push the envelope, show your personality, or have a little fun.

Example Drip Emails

Let’s take a look at a whole bunch of email examples. Review these with a critical eye. Think about what I’ve taught you and look for the techniques in practice in these emails.

Auto Insurance Example

Email #1 - Day 0
SL: Did you get your car insurance quote?SL: There’s always a better rate

Just checking in to see if you got the new auto policy you were looking for. 

If not, I’d be happy to assist.


P.S., Go ahead and save this email for the future. I want to be your insurance guy!
Email #2 - Day 2-3
SL: I really want to be your insurance guy!

I know you recently requested an online insurance quote. 

We didn’t connect at that time, but I REALLY want to be your go-to insurance person!

Anytime you have an insurance question or need a quick quote - email or call me and you’ll be my top priority.


P.S., Do you have a policy you’d like to review or have questions about? 
I’m available anytime - even for quick questions.
Email #3 - Day 10
SL: I’m here when you need me
SL: File this away for a rainy day

It’s a good practice to check your insurance policies for a better rate at least every 6 months. 

Why? Life changes. Situations change. Insurance products change. Sometimes the world even changes. 

I want to be your go-to insurance person in those moments. So, file this in your archived emails and then search for “my insurance guy” when you need me.

Email or call me with any questions - you’ll be my top priority.


Example Nurturing Sequence

Email #4 - Day +7
SL: The “secrets” most car insurance providers never tell you.


Ok, they’re not exactly secrets, hence the quotes, but a lot of agents don’t tell their clients this stuff upfront. 

Here are three of the biggest things some insurance folks are leaving out…

Good credit means a lower payment, every time. Every insurance provider is going to pull your credit report. If your credit is suffering you’ll have to pay more no matter who you go to.

Pay in full if you can. If you pay for the whole year upfront you avoid all the fractional costs or installment fees insurance companies love to collect.

Know what your car is really worth and what the insurance company thinks its worth. They don’t use Kelly Blue Book, often if you want total coverage for a potentially totaled car you may need gap insurance. (I’ll help you assess this, no problem)

Of course, there’s more and I’m glad to give you the skinny on all of it and answer any questions you might have. 

Hit reply, call me or take a quick moment to answer a couple of questions here and we can finish what you started and see about lowering what you’re spending on car insurance. 

Best Regards,
Email #5 - Day +14

SL: Did you know that taking a defensive driving course could lower your insurance?

Hi {{contact.first_name}},

No joke, depending on where you live a short defensive driving course can actually lower the cost of your insurance. 

In fact, there are more than a few unorthodox discounts and programs you can leverage to pay less. Some are advertised, many are not, but all of them depend on where you live.

You may have forgotten, but my name is {{user.first_name}} with {{company.name}} and while back I know you were on the hunt for a better deal and you may or may not have gotten all the info you needed to generate the best possible quote. 

Reply to this email, give me a call, or answer a couple of quick questions on my profile page and I’d be happy to get you a new quote. 

I’ll also make sure to check for the eligible discounts and programs available to you based on where you live. 

Talk to you soon! 


Email #6 - Day +21

SL:  Buyer beware, the cheapest insurance could be a scam.

Hi {{user.first_name}},

The one thing I always want to make sure my clients know is that I’m here to get them the best price on quality insurance, but I can’t compete with the scammers.

No matter where you get your car insurance be on the lookout for these two common scams.  

The Fake Agent: The most common scammers are just con artists posing as insurance agents selling fake policies. If everything is too good to be true just ask for a copy of the agent’s license, that’ll put a stop to things. 

The Ultra Cheap Policy: These policies are real but they often don’t meet the minimum requirements of your state. Do a little research and make sure you’re actually buying coverage that protects you and meets the criteria under the law. 

If you’re not looking for a better rate on your car insurance anymore just let me know by replying to this email.  

If you think that deal was too sweet, show me what you have and I’ll put your mind at ease.

Or… if you’re still on the lookout for quality coverage at a better rate I’m eager to run the numbers, identify your eligible discounts, and get you the best deal I can. A real deal. 

Stay vigilant! 

Email #7 - Day +28

SL:  Just a quick check in

Hi {{contact.first_name | there}},

It’s me again, {{user.first_name}} from {{company.name}}. I hope you’ve found some of the stuff I’ve been sending useful. 

Did you ever get a quote on your new car insurance that you liked? 

If you’re all set, fantastic. Reply to the email and let me know I can stop pestering you. If you didn’t or you’re still looking for a better deal I’m here to help. 

Drop me a note by replying to this email one way or another. 



Other Examples

Day 0 - Instant Home Offer
SL: Just checking in
SL: Still thinking about selling?
Preheader: I wanted to see where you’re at
Preheader: Now is a pretty good time

Hi {{contact.first_name | there}}!

This is {{user.first_name}} from {{company_name}} (we just changed our name from Old Company Name). What do you think? 

We talked a couple of months ago about selling your house. But, didn’t really move forward.

Are you still thinking about selling?

Day 3 - Instant Home Offer
SL: What did you decide?
SL: Curious...
Preheader: What did you decide to do
Preheader: Are you hanging on to the house

{{user.first_name}} again.

Just curious - did you already sell? 

It’s okay if you went in a different direction. Just wanted to make sure you got what you needed.

P.S., If you did sell, I’d love to know what you got for it.
Day 10 - Instant Home Offer
SL: I thought I would try one more time
SL: If you’re not ready, no problem
Preheader: Just wanted to see where you landed
Preheader: Are you hanging onto the house

{{contact.first_name}}, I thought I would check in one more time.

Just curious...
Did you sell or decide to wait?
 * If you did sell, what did you get for it?
 * If you're waiting, what changed?
 * I’m always trying to understand how to help folks like you better. 

If you’re just waiting let me know. I can always let know what the market is doing.

P.S., I can typically match or beat any offer. So, never sell without giving me a shot.
Day 1 - Personal Service General
SL: I just finished this. Thought it might be interesting
SL: Working on {{service}} for {{client like you}}
Preheader: Take a look at the results
Preheader: Quick case study for {{industry}}


I’m {{user.first_name}}, from {{company_name}}. We {{just finished up | are working on}} this project designed to {{business_objective}}.

I thought you might be interested in the case study. Take a look.

Happy to answer any questions.

Day 3 - Personal Service General
SL: What did you think?
Preheader: Are you doing is


Are you doing anything like this currently? 

I’d love to walk you through our process and how it might help your business.

Interested in setting up a 15 min call?

P.S., Feel free to grab a time on my calendar that is convenient for you.

What questions did I leave you with? Too much to process or you just want someone to do it for you?

No problem, check out my lead nurturing service.

We nurture up to 2,500 of your leads a month – for only $500/month.

About Bill Rice
Bill Rice is the Founder & CEO of Kaleidico. Bill is an expert in designing online lead generation strategies and programs. Kaleidico blends web design, development, SEO, PPC, content marketing, and email marketing to generate leads for mortgage lenders, law firms, fintech, and other businesses looking to grow a consumer-direct online strategy.

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