You don’t know jack about SMS

Daniel Brain
9 min readAug 5, 2022


I mean, how hard can it be? Aim Twilio at a phone number and turn it on.

Hol’ up

Yeah, let’s not get ahead of ourselves.

A bunch of different brands have started to use SMS to communicate with their customers. The only problem is, they all decided to do it like this:

This is a “billboard style” SMS message. And it’s indescribably shitty.

Why do you care?

Full disclosure: other than being inundated daily with awful text messages like the one above, I’m also actively working on a solution for this problem.

My co-founder Jonathan and I recently left PayPal Checkout, to start a platform called OneText. (Want to find out more about it? Shoot me an email or hit me up on Twitter)

While building OneText, we learned the ideal way to do SMS for humans. Here’s what we figured out.

Talk like a human!

This is an easy one.

Humans in real life do not talk LIKE THIS, 20% OFF reply STOP to opt out.

Humans talk in regular sentences. Your SMS messages should too. Seriously — people value being talked to, not being talked at.

Be conversational. Reply!

The best thing about SMS messaging is, it’s conversational! I can reply to messages, and I don’t have to deal with anyone face to face if I don’t want to.

I’m an introvert at heart so I love that. But regardless — being able to reply to a text message and know I’ll get a response with exactly what I need, is just so damn convenient.

Reply anytime

We see a lot of platforms restricting messaging to daylight hours.

That makes perfect sense for cold outgoing messages. But when a customer has actually messaged you and wants an answer? Just reply!

Don’t send links up front!

This goes back to the billboard thing. If you send a link in your very first text, your message will usually be ignored, or at best you’ll get a click and an immediate drop-off.

Ask a question, or say something that warrants a response. Even ‘reply yes’ is an acceptable thing to start off a conversation.

We ran a split AB test at OneText because we were convinced about this one and we wanted to prove it. We found we got a significantly higher overall conversion rate when we didn’t send a link up front.

When you do send a link, make it count

Eventually you will probably need to send out a link. That’s fine. But make it count:

  • Send the link when it’s a natural part of the conversation, not before.
  • Take the customer exactly where they need to go. If you just link to your home page, you’re probably doing it wrong.
  • Don’t send a coupon code alongside the link. Nobody should have to memorize, copy, or write that down. Your link should include any discounts you want to give the customer.
  • Use the actual domain of your site in the link. Not some spammy looking shortened url that looks and feels untrustworthy.

Genuinely: make the link count.

One thing we’ve learned while building OneText is, it’s best to take the customer from the SMS thread, directly to where they need to be:

  • There are no extra clicks
  • All available details are pre-filled and ready
  • The only thing left to do is fill out your payment details and complete the purchase.

It’s amazing to see the number of real payment flows out there with page after page of forms and offers before you’re finally done.

Keep it simple!

Let the customer purchase in the SMS thread

What’s the point of being conversational if you can’t just reply to complete your purchase?

This should be table-stakes for all SMS based sales. It’s one of the first things we built at OneText, and so far people love it.

We’re super glad to see PostScript and Attentive following our lead here! It really is the way to go.

Make it easy to opt-out

Not everyone wants to receive SMS messages.

Yes, they gave you their phone number — no, that does not give you a carte-blanche to message them if they don’t want you to.

Many providers require you to message STOP to opt-out. But we can do better than that. If the customer asks you to stop, that should be enough.

Let customers schedule orders

You’d be amazed at the number of people who are incredibly receptive to conversational SMS, but they just aren’t ready to buy this instant.

You should be prepared for that, and able to handle those cases.

Start with one-time orders, then subscribe

Nobody really wants to be forced into a subscription the first time they check out. Everyone knows how hard it is to cancel, especially for a product they haven’t tried yet.

Let your customer make a purchase and save their card, then help them set up a subscription (or just a simple re-order) when they’ve tried the product and when they’re ready.

Give a safety window for payments

If you’re going to charge customers for subscriptions and re-orders, you need to do it ethically and honestly. We see far too many providers who make it virtually impossible to stop a subscription, or even find out when they’re going to be charged.

We wanted to fix this too. That’s why we built a 24 hour delay into all repeat purchases, with the opportunity to cancel or skip.

Our theory: a customer is much more likely to opt-in to a subscription, if they know it’s not going to be a hellish task to get out of it later.

Don’t fake attribution

One completely bizarre thing we’ve seen in the SMS space, is attribution models that make your head spin.

Providers will send an SMS message to a customer. Three or four days later, that customer might make a purchase — whether they saw the message or not. The SMS provider will then claim attribution and take the credit for the sale.

This is madness. If you want attribution for a sale, you should be the one to actually make that sale, and you should be able to prove it.

We fixed this at OneText by using unique-per-customer links, and text-to-pay. There’s never any doubt or ambiguity about who is responsible for the sale.

Don’t do this…

Keep your customers

Most brands care very strongly about keeping a relationship with their customers, especially the loyal ones. They’re (rightly) concerned about preserving their email and SMS lists.

But nobody ever stops to think about their customers’ wallets.

Real world example: let’s say the majority of your customers save their credit card on Shop Pay, and then later Shopify decides they don’t want to process your brand’s payments any more. What happens then?

We’ve literally seen this exact situation happen, more than once.

We wanted to fix this at OneText by providing a ‘portable wallet’ for customers.

Customers can vault their credit card to do text-to-pay. Once they’ve done that, as a merchant you’re free to direct payments to any processor. Maybe today you use Stripe, and tomorrow you decide to switch to PayPal. You just bring all of your customers with you, along with their wallets. Those customers don’t even need to know — or care — that anything has changed!

Let your customers message you first

One of the amazing emergent things we started to see (that we didn’t initially expect) was that customers started proactively reaching out and messaging us, rather than just responding to our messages.

It’s a golden opportunity to actually be there when the customer needs you.

Campaigns are OK, events are better

One option with SMS is just to run a campaign, to message an entire population with a promotion. But this is fairly impersonal, and actually we’ve found that more people opt-out when we do this style of messaging.

SMS messages are much better when they’re actually relevant to you — specifically something that you just did, or something that just happened to you.

Maybe you just abandoned a cart, maybe you just got a delivery, maybe your favorite product was just re-stocked. All of these are better reasons to text someone than “we’re having a sale!”

Learn from your customers

With any other platform, whether it’s a web store, or an email campaign, it’s pretty rare for people to actually respond or message you back.

With SMS, that’s completely different. Customers will tell you what they want, what they like, and what they don’t like.

It’s crucial to learn from that and adapt how you sell.

Build Trust

Quite often, customers just want a little bit of reassurance, and to build trust.

They’re purchasing from you for the first time, they don’t yet have a relationship with your brand — and a bit of back-and-forth goes a long way to starting to establish that trust.

Building that trust should be your first objective. Selling comes second. Once you have trust, selling is easy.

Go forth and SMS the right way!

I’d love to see a world where SMS messages from brands are designed for humans, and focused around conversations.

Feel free to go and try any of this for yourself — you’ll see it works incredibly well. There’s really no excuse (or need) to send spammy billboard style SMS messages.

If you want to do it the easy way, shoot me an email or message me on Twitter. Everything you see above, we’ve built into OneText. It all works out of the box — and much of it is automated, so you can just set it and forget it.

Try it out by scanning this QR for a (basic) demo of one use case:

Scan me on your phone to try it out!

But seriously — even if you don’t talk to us, please steal all of these ideas. They’re free, and you (and everyone you message) will benefit massively from them.

— Daniel, Chief “guy who churns out code” @ OneText