Getting to the Second Sale

The Make or Break Moment for Ecommerce Brands

Author

Pietro Saccomani
March 27, 2025

We can go deep into the weeds in terms of email, SMS, push marketing, loyalty programs, retargeting, and a hundred other subjects.

But really, retention often comes down to specific moments and milestones.

Success (and long-term profits) often come from nurturing more buyers towards the second purchase.

This is a breaking point where customer relationships are cemented, and customers become much more likely to spend much more money with you as time goes on.

Today I’m going to break down why this is such an important milestone for retention and LTV, and how you can get more of your customers to this key inflection point.

I’m excited for this one. So let’s get into it!

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The snowball effect of repeat purchases

Research consistently shows that the second purchase is the critical inflection point in customer behavior—it's where the snowball starts rolling.

Consider these statistics:

  • Omniconvert found just a 25% chance a customer will return after making one purchase. But once they make purchase #2, the probability of a third order jumps to 41%.

  • Each additional purchase significantly increases the odds of another: roughly 52% for a fourth order, 59% for a fifth, and by the sixth or seventh purchase, the chances climb to 65-70% or higher.

  • According to Adobe's Digital Index, first-time buyers have a 27% likelihood of returning, but after two or three purchases, this grows to 54%.

  • Even more dramatic, RJMetrics found that while only 32% of customers place a second order within their first year, those who do have a 53% likelihood of making a third purchase, climbing to 64% for a fourth and approximately 70% by the fifth purchase.

Not only do repeat customers buy more frequently, but they also spend more per order.

Bain & Company studied online shopping habits and discovered that in apparel, a shopper's fifth purchase was 40% larger than their first, and by the tenth purchase, the value had increased by an impressive 80%.

See the snowball taking shape?

Return customers drive sustainable growth

Why do return customers matter so much?

On a pound for pound basis, a sale to a returning customer is usually worth more to your business than one to a new customer.

Research shows that retaining just 10% more first-time buyers can double your revenue.

Here’s why.

They’re cheaper. Return customers typically come from low-cost channels like email, or direct website visits; unlike new customers, who often originate from expensive paid ads.

According to Boston Consulting Group, the cost of marketing to existing customers averages around $7, while acquiring new customers costs approximately $34.

They’re easier to convert. Well-known textbook Marketing Metrics states that the probability of selling to an existing customer is 60-70%, compared to just 5-20% for new prospects.

Since they’ve gotten over the trust barrier, conversions are much easier, and you’re less likely to rely on discounts that sap margins.

They’re less price sensitive. Once someone has bought from you already, and they know what they’re getting, customers are typically more liberal with what they’re willing to pay, as they’re not just comparing on price – but considering the value they know they’re getting with you.

Return customers are where your margins are.

Many brands don’t make a profit (or make little profit) on the first sale.

Higher acquisition costs + lower AOV + incentives needed to push a first-time buyer into converting means a lot of brands aren’t sustainable with just one-time buyers.

You start making real profits on the second sale, so you want to get there as soon as possible.

The urgency of securing that second sale

Profitability begins with the second purchase—and timing is everything.

For one, because your business doesn’t run on implied future sales.

It’s great to have a plan in place for making up first-order losses with retention… but you’ve gotta get to profitability soon, or you’ll run out of money.

Generally, you want to be profitable within 13 weeks of first acquisition at the latest (but this can change from business to business).

But in any case, the sooner you’re making a profit from a customer, the better.

The second reason this second sale needs to come fast is that it cements the customer relationship—and shorter time to second sale tends to correlate with higher long-term retention.

It’s been stated that customers who make their second purchase within 60 days have higher repeat purchase potential and higher LTV.

When it comes early, your brand is really imprinted in the customer’s mind (it’s also easier and cheaper to convert them when it’s a shorter time from the first purchase).

If the second purchase comes a year and a half after the first, it’s basically like acquiring them from the start again, and you lose a lot of the juice we’re talking about here.

Repeat business has varying levels of importance from brand to brand. Brands in naturally high-ticket, low-frequency categories will be less focused on repeat purchases (profitable acquisition is non-negotiable). But the meaty part of the bell curve is brands where the second purchase is the major inflection point for LTV.

How to get more one-time buyers to the second sale

We know how important the second sale is—and that you need it sooner, rather than later.

But let’s talk action. How can we get to sale #2 more regularly… and within that key 30-60 day window?

Email, SMS, etc… you know the script. Retention marketing is nothing new.

But here are a few high-impact strategies most brands aren’t doing.

1. A truly memorable post-purchase experience

You want your customers to remember the feeling they got when buying from you.

Clear communication, their order arriving on time, and a cool unboxing experience all go into a memorable post-purchase experience.

So does sharing content that helps them get more value out of their purchase (product guides, tutorials, videos).

An underrated tactic? Random thank you gifts.

Send something to the customer out of the blue, aligned with their interests, just to say “thanks for buying from us.”

No ask, no strings attached.

This makes the customer feel special, and really valued… and ensures they’ll remember your brand when they’re in market to buy again.

2. Nurturing mindshare with multiple touchpoints

Your biggest barrier to getting the second sales is the customer forgetting about your brand.

Once someone becomes a customer, use the post-purchase window to build multiple touchpoints you can use to reach out to them in the future.

You’ll have their email, but you can’t rely on email alone. The more touchpoints you have, the better.

  • SMS

  • App download

  • Social media follows

  • Community memberships

More channels gives you a higher surface area to nurture the relationship towards the second sale.

Once you build these touchpoints, use them—not just to sell.

Use them to build mindshare. Constant communications, not always promotional, keeping your brand top of mind.

Good push notifications can sell - or just keep your brand in the customer’s mind.

Email and push are the best channels for this; minimally invasive, cheap, great at keeping your customers warm and engaged.

Then when the time is right, you hit them with the offer. Much better than going dark and only messaging the customer weeks later, asking for them to buy again.

3. Time your next offer correctly

Timing is crucial. You can send great offers that fall flat because the customer just isn’t in the market to buy.

Analyze your customer data to identify when most second purchases occur (often between 30-60 days after the first).

Create targeted offers during this window, when customers are most likely to be considering their next purchase.

This is easy with consumables—time your second purchase offers to come in just before the customer is due to run out.

Consider that, at any given time, most of your audience (90%+) are not in-market to buy.

Reaching them with the right offer, at the right time, can make a huge difference on how many people you get coming back for purchase #2.

4. Encouraging community interaction

Post-purchase, encourage customers to share their experiences on social media or within your brand community.

This is valuable for two reasons.

One, it creates UGC that helps to attract and convert new buyers.

But two (and most importantly for retention), it strengthens the customer’s connection to your brand.

It makes them feel part of a community; a core desire in every human being.

This makes a huge difference vs making a purchase from a forgettable, faceless brand.

Small shifts have a big impact

The second sale is the make-or-break moment for most ecommerce brands.

You don't need to revolutionize your entire business model to see substantial results.

Even modest improvements in:

  1. The percentage of customers who make a second purchase

  2. How quickly they make that second purchase

can transform your business in 2025.

Nurture your customers towards this milestone, then let the snowball start to build from there.

A small boost in the number of customers coming back for purchase #2 will make an outsized contribution towards LTV and profit, and help you survive the current market conditions while other brands around you continue to struggle.

Quick Hits

What‘s worth your attention from around the ecom & DTC world this week.

The Creative Disruptor Everyone’s Talking About

If you haven’t noticed yet… Chat GPT just changed the game.

Their new image editor lets you create amazing images with just a simple prompt… it became a real graphic designer overnight.

There have been examples all over the internet in the last 24 hours of marketers playing around with it and mocking up ads that could easily have come from a billion dollar brand.

It’s wild what people are making with just an image and a prompt (here’s a great thread with more examples). Try it out yourself — iteration for ad creative will never be the same.

Shein and Temu Claim a High-Profile Victim

As Forever 21 prepare to close all their US stores, court filings have revealed that key people in the company blame Shein and Temu for their bankruptcy — saying Forever 21 was “materially and negatively impacted” by Shein and Temu’s use of the de minimis exemption, and that the two discount retailers undercut Forever 21’s business.

How Post-Purchase Surveys Can Shape Your Creative, Messaging, and More

Max’s post on LinkedIn shares great insights on a simple thing you can do post-purchase to max more customer-centric decisions for your brand moving forward: post-purchase surveys.

It’s wild that more brands aren’t making this direct customer communication a priority.

US Online Spending to Hit $1.4 Trillion This Year

While a lot of brands are feeling the pinch in DTC, there’s at least one reason for optimism: consumer spending is not slowing down.

Expectations are that online spending will cross $1.4 trillion in the US this year ($4.4 trillion worldwide).

For context, Digital Commerce 360 puts this figure at $1.192 for 2024 — and in 2019, it was less than half, at $571.088 billion.

Despite the rate at which online spending continues to grow, ecommerce only makes up 16.1% of total US retail sales, meaning there’s still plenty of room for further growth.

5 Ways to Make More Profit

For all the strategic tips and tricks being sold to you, ecommerce (business in general, really) comes down to one thing: profit.

In another great Operators Newsletter, Mehtab Bhogal from Karta Ventures talks about the top 5 ways for your business to make more profit — some extremely simple tips, which you can put in action overnight.

That’s everything for now.

Same time next week, I’ll be back with more to help you level up your business with retention marketing and CX.

If you’ve got any ideas for what you want to see in a future deep dive, hit reply and let me know. Same goes if you’ve got any thoughts on the content in today’s newsletter — always great to hear other perspectives.

Keep an eye out too on social media (and our YouTube) for the brand new Retention Edge Podcast.

We’re just about to drop the first episode, and I think you’re going to like what we’ve got for you. We’ve lined up some of the best CX minds in retail to share real insights about what’s really working for high-level brands, and the first few episodes are not going to disappoint.

Until next time,

Pietro and The Retention Edge Team