Retention 101: A 2-Year Plan to Keep Every Customer You Win

A practical guide to retention for ecom brands, SaaS, coaches and freelancers, starting from your ICP.

I’m about to fast-track your path to more repeat sales, more revenue from every customer, and customers who stay for years, all starting from your ICP.

The reality is, keeping customers is a lot simpler than most people make it out to be. The problem is, most people think they’ll have a business as long as they keep getting new customers. That’s far from true. If you can’t keep the customers you already have, you’ll never have a profitable business. My goal with this guide is to show you where retention really starts and give you a plan you can use today.

This guide shows you:

• Why you can’t keep the customers you win, and the one step you missed

• The 7 questions your ICP must answer

• How to map a 2-year retention plan on day 1

• How to sell the right thing at the right time

This is the full 3-step plan that, if you follow it, already puts you ahead of 99% of businesses in your space. It works whether you run an ecom brand or a SaaS, or you’re a freelancer working with coaches and creators.

By the way, if you find this useful, a like, follow and restack go a long way. I put a lot of hours into these.

Building an ICP That Keeps Customers

If you take away only one thing from this article, make it this: retention starts when you create your ICP, way before your first customer.

In other words, you plan the second sale before you make the first one. Most businesses plan the ad, the offer and the price for the first sale. They never plan what the customer will need after that. So when the customer’s needs change, they buy from someone else.

Planning this way also fixes three problems most businesses blame on marketing. Customers buy once and never come back. Revenue swings from month to month. Ad costs keep rising, because you have to replace every customer you lose.

Ultimately, a retention ICP tells you:

• Where your customer is on the day they buy

• Where they will be in 3, 12 and 24 months

• What they will need from you at each point

Of course, there’s more to retention than this. But if you get these three right, you’ll know what to sell before your customer needs it.

How to build your retention ICP

1. Start with the ICP you have

Keep whatever ICP you use now. Age, job, pain, budget, all of it. Then make sure it answers these 7 questions about your best customer:

Where are they today?            → Their stage on the day they buy
What made them buy now?          → The trigger, and why not last month
What proves they chose right?    → Their first result with you
What big change comes next?      → Their next milestone
What breaks when it happens?     → Their next problem
What would make them leave?      → Their reason to stop buying
When will they outgrow you?      → What you can sell them then

Once you answer these questions, it becomes much easier to plan the offers, emails and products that keep customers buying.

2. Map the next 24 months

Once you’re clear on who your customer is today, picture them 24 months after they buy. Where are they? What do they own? What do they worry about?

Then list every big change between the day they buy and that point. I’ll call these changes milestones. Each milestone is a moment when your customer will buy something. Your plan makes sure they buy it from you.

For example, say you sell a booking app to hair salons. Here’s how one salon owner’s next 24 months could look:

When        What changes for the salon owner         What you sell her
───────────────────────────────────────────────────────────────────────
Month 0     She works alone and books by text        The booking app
Month 4     She's fully booked, turns people away    Deposits and a waitlist
Month 9     She hires her first stylist              Team seats and payroll
Month 15    Her chairs sit empty on weekdays         Automatic rebooking
Month 24    She opens a second salon                 The multi-location plan

Look at month 9. She hires her first stylist. If your app has no team plan, she switches to an app that does. You lose her because your product had no next step for her.

Another example is a prenatal vitamin brand. Here’s how one customer’s next 24 months could look:

When        What changes for the customer            What you sell her
───────────────────────────────────────────────────────────────────────
Month 0     She's trying to get pregnant             Prenatal vitamins
Month 3     She's pregnant                           The pregnancy bundle
Month 10    Her baby is born                         Postnatal vitamins
Month 18    She's back at work and tired             The iron and energy line
Month 24    Her baby starts solid food               Kids' vitamins

Once her baby is born, she no longer needs prenatal vitamins. A brand with nothing to sell her at month 10 loses her that day. A brand that planned for month 10 can keep her for years.

Your product plan and your retention plan are closely tied. Every new product or feature should serve one of these milestones. If it doesn’t, you’re guessing.

If you sell to businesses, look for changes in their business. If you sell to people, look for changes in their life:

If you sell to businesses     If you sell to people
──────────────────────────────────────────────────
First hire                    New job
Bigger revenue tier           Moving house
New location                  Getting married
New tool or platform          New baby
Tax season, audits            Kids start school
Raising money                 New fitness goal
Selling the business          Retirement

Note that your customers won’t all hit these milestones at the same time. That’s fine. The map tells you what to sell. The next step tells you when.

3. Find the signals

Your map is what you sell, but the signal is when you sell it.

• Ask at signup. “When is your due date?” or “How many stylists do you have?” tells you what’s coming.

• Watch usage. More bookings, more seats or bigger orders mean they’re growing.

• Watch gaps. A late order or a login that stops means they may leave.

• Read support tickets. Customers often mention their next problem there.

For example, a baby brand that asks for the due date at signup doesn’t have to guess when month 10 is. It waits for the date.

For a B2B product, the team size works the same way. When the number of seats goes up, the owner just hired.

TL;DR of building your retention ICP:

1. Make your ICP answer the 7 questions

2. Picture your customer at month 24 and list every milestone on the way

3. Find the signal that tells you each milestone just happened

Choosing Your Offers

An offer is just what you sell at a milestone. A refill, an upgrade, a new product, a call.

Every offer does one of three jobs:

1. It stops new customers from leaving early

2. It sells more to customers who stay

3. It gives customers who outgrow you a next step

To keep a customer for two years, you need all three. Each job covers a different part of those 24 months.

How I think about the different offers:

Offer           Job                                      Effort
──────────────────────────────────────────────────────────────────
Setup help      Stops new customers leaving early        Low
Win-back offer  Brings back customers who left           Low
Refill          Sells more to customers who stay         Low
Upgrade         Sells more to customers who stay         Low to medium
Add-on          Sells more at a milestone                Medium
Next product    Next step for customers who outgrow you  Medium
Next program    Next step for clients who got a result   High

How to pick

Don’t try to build every offer at once. Just start with 1 or 2 milestones.

Ask yourself:

• At what point do most of my customers leave?

e.g., if most leave in the first month, start with setup help. If most leave after a year, start with the next product.

• What do my customers buy from someone else after they buy from me?

• What do my best customers ask for that I don’t sell?

Each offer, summarized:

1. Setup help

The cheapest way to stop customers leaving early. A customer who gets their first result in week one is far more likely to stay.

Use it when  → Customers leave in the first weeks
Suits        → Software, coaching, anything that takes effort to learn

2. Win-back offer

For customers who already left. Name the milestone they were at when they left, and offer the thing they needed then.

Use it when  → You have a list of past customers
Suits        → Everyone, eventually

3. Refill

The easiest repeat sale you’ll make. Time it to when the product runs out, not to a date on your calendar.

Use it when  → Your product gets used up
Suits        → Supplements, skincare, coffee, pet food

4. Upgrade

The customer grew, so their plan should grow with them. Offer it at the milestone, not at random.

Use it when  → The customer's business or needs got bigger
Suits        → Software, memberships, coaching tiers

5. Add-on

A small fix for a new problem. The salon owner’s waitlist is an add-on.

Use it when  → A milestone creates a new problem
Suits        → Any business whose customers hit clear milestones

6. Next product

The new stage needs a new product. The postnatal vitamin is a next product.

Use it when  → The customer outgrows what they bought
Suits        → Brands with a range, or room to build one

7. Next program

For coaches and course sellers. The client got the result they paid for. Now they want the next one.

Use it when  → A client finishes your program
Suits        → Coaches, creators, info products

You don’t need all seven at the start. Again, focus on the point where most of your customers leave, and build the offer for that point first.

Every offer has a different job. Setup help keeps new customers. Refills and upgrades grow the ones who stay. The next product keeps the ones who would otherwise outgrow you.

Depending on your business, you’ll lean on some offers more than others. For example, an ecom brand might lean on refills, while a coach leans on the next program.

Timing & Messaging

This is where most businesses lose the sale.

You can have the right offer for the right milestone, and still get no sales.

In my experience, timing is the most underrated part of retention. Most teams put almost all their effort into the offer and almost none into when and how it reaches the customer. It should be closer to 50/50.

Timing is:

1. The trigger

Send the offer when the milestone happens, not on a fixed day. “Day 30” is a guess. “She just hired her first stylist” is a fact.

2. The first line

Say what changed for them. Write “Your new stylist starts Monday,” not “Check out our team plan.” The customer should feel that you know where they are.

3. The channel

Use email for most offers, SMS for refills that are about to run out, in-app messages for software upgrades and a call for your biggest offers.

4. The first few days

Move fast. The longer you wait after a milestone, the more likely the customer has already solved the problem somewhere else.

Messaging

1. Write for the moment

A new mom at 2 AM won’t read a long email. A salon owner on a Monday morning will. Write for the person at that milestone.

2. Make it one click

Reorder in one tap. Upgrade in one click. Every extra step loses customers at the exact moment they want to buy.

Final Advice & Recap

So, to recap the process of building a 2-year retention plan:

1. Build your retention ICP: answer the 7 questions about your best customer

2. Map the milestones: picture them at month 24 and list every big change on the way

3. Choose your offers: start with the point where most customers leave

4. Time it: send the offer the day the milestone happens, say what changed in the first line, and make it one click

A few tips I’ve picked up:

• Ask milestone questions at signup. A due date or a team size tells you more than a birthday.

• Read every cancel reason. Customers tell you which milestone you missed.

• Double down on what works. When one milestone offer sells, build the offer for the next milestone.

• Tell customers about the next offer a month before they need it.

• Have every offer mention the next one. The refill email mentions the bundle. The bundle mentions the next product.

Closing

I genuinely think if you follow this guide, you’ll keep more of the customers you win and grow revenue without spending more on ads. It’s how I think about every account I work on.

If you made it this far, thank you for reading.

If you found even one useful point in this piece, a like, restack and follow go a long way.

If you have questions about mapping your own customer’s milestones, leave them in the comments below, and I’ll reply to every one.

I plan to write 1 to 2 of these a week. If you have ideas on what you’d like me to cover next, drop them below.

Want this mapped for your business? Reply to this email or DM me “RETENTION”. I’ll send you 3 to 5 places where your business loses revenue from customers you already have, within 48 hours. Free.