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250,000 Automated DMs Sent. Here’s What Worked - And What You Need To Avoid.

Essential reading for anyone thinking about LinkedIn automation tools.

This week, we’re going to dive into our past approach to LinkedIn marketing.

Namely: LinkedIn Direct Messaging Automation


We’ve run campaigns for ourselves and regularly speak to companies using these kinds of tools for over a year now.

We also know that a lot of people are either thinking about them or trying to understand how to better their performance with such tools.

This article is about understanding our successes, our failures, and the pitfalls to watch out for if you want to try something similar.

First: let’s break the taboo about automated messaging.

The First Rule Of Automated Messaging…

Let’s be honest.

Nobody talks about it, but millions of people do it (by our calculations).

It’s against LinkedIn’s rules. That doesn’t stop anyone apart from the worst offenders.

But there’s no point beating around the bush.

It happens. You know it happens, because you receive them every day.

Plus, in a limited way, it is an effective strategy.

But pulling all the numbers together - starts to paint an interesting picture.

The Numbers, At A Glance

What this shows you is that LinkedIn automation can get you sales calls.

And it is much cheaper than other lead generation activity.

But here is the issue.

It is easy to have calls.

It is really hard to sell on these calls.


You are starting from cold position.

Yes, these leads are intrigued. It doesn’t mean they have signalled intent.

This is often what gets forgotten:

The seller starts with the assumption that the buyer wants to buy.

The buyer starts with an an interest in the conversation. But it doesn’t mean they are ready to buy.

Plus - you are against stiff competition

From the state of your inbox, you probably feel like everyone is doing it. My connections agree:

In other words: if you are on LinkedIn, you will be spammed.

While most people only get a couple per day, others reported a much higher volume.

But even if you do only get a few in a day, that number builds up quickly over the course of a month.

That’s not to say that all of the messages you get are spam, per se. Some of them could genuinely help you.

And it’s not always a bad thing to go down the automated messaging route to offer your product.

But if you do, we have learned a few practical tips that can help you. Like:

  • Tailor your audience precisely using Sales Navigator and use your messaging to address their pain points - be specific, rather than generalised.

  • Include at least three follow-up messages - most of our success came after message 4 or 5.

  • Keep your messages short and punchy - your audience gets so many messages that you only have a few lines to make your point.

But even if your messages do resonate, you're still starting from cold.

You can sell from here, but you most likely won’t, because:

  • They don’t really know you.

  • They don’t know whether what you do can solve their problem.

  • They might not even know what their problem is.

In short: they don’t have enough trust in you.

Which means this model is essentially pitching and hoping. Usually, that doesn’t work.

Over time, we realised that automated messaging is just the first link in the chain, rather than the be-all and end-all.

Which means you have to change your process - to one that focuses on proving you can solve their problem.

It Shouldn’t All Be About The Sales Call

Most small business LinkedIn sales processes are essentially this:

Our own process started off like this, too.

It was a logical chain.

But it also put a huge amount of pressure on that sales call.

In that sales call, you need to build a rapport, explain your product, work out your customer’s problem, apply your product to that problem, and convince them to have enough faith in you to continue.

All that - in maybe an hour? Less?

It’s too much. And it was the key point of failure.

We noticed that calls are easy to get, but really hard to get them to go further than that.

This was the same for both us and most of the businesses we spoke to.

To use a dating analogy: we could get them to go out for dinner once. We couldn’t get them to go any further.

By the way - the automated messaging had actually done its job in this instance by getting us through the door.

The issue: by definition, it is really difficult to build a genuine relationship through automated messaging alone..

Our solution?

A longer-form sales process, based around relationship-building through engaging content.

Here’s what ours looks like now:

It’s much longer. It’s more work on our side. It’s also much more effective at getting that final sale.

The DM pitch-slap feels like it works because you always get a few hits. But take it from us - it’s not a sustainable solution.

Instead, focus on longer, deeper relationships with your audience.

Engage them with meaningful, insightful content.

Offer genuine value to them, rather than focusing all your energy on getting them to sign a contract.

Focus on getting them warmed up to you before you’ve even spoken to them.

The more this happens, the easier your sales conversations become.

Change Your Pitch, Don’t Get Slapped

They say you should never talk about religion, money or politics.

We’d suggest adding LinkedIn DM automation to that list.

But everyone’s doing it. So there’s no point keeping it under the rug.

We’ve tried the pitch-slap approach with countless campaigns. For ourselves, for our clients.

And it can work. But it’s hard work. Most small businesses don’t have the capacity to handle it and they have a tendency to blame the leads rather than understand that the sales process needs to be better.

Warming up your leads does take longer, but it’s less intense - and there’s less chance of failure.

If you’re not worried about making a sale straight away, you’ll be more at ease - and therefore much more likely to make that sale.

You can use automated outreach to accentuate what you’re doing, but the core of it needs to be personalised, sustained, and long-term.

If you’re thinking about your marketing more broadly, and want to understand your strengths and weaknesses, our free LinkedIn marketing assessment can point you in the right direction and give you a benchmark to work against.

Now, as promised…

My Conspiracy Theory About LinkedIn

LinkedIn says automation is against the rules.

But tens of thousands of accounts freely do it.

Why? Because LinkedIn gets £80 a month, per account, for Sales Navigator (which is necessary to enable automation).

My theory: LinkedIn turns a blind eye because they make so much money out of it.

At most, they stop the worst offenders. So they look like they’re cracking down on it, but leave most people to get away with it.

Which leaves LinkedIn like this:

That's all from me for now. Till next week.


It can be a long process to get this all in place, but I’d love to hear if these insights work for you. You can DM me via LinkedIn or reply to this email with your thoughts or any questions you might have.

And if you’d prefer some direct feedback on your LinkedIn marketing efforts, I’d be happy to help. You can take our LinkedIn assessment and I’ll follow up with some free analysis a few days later.