Cold LinkedIn pitches that led to demos: forget the bad, here’s the good

Cold LinkedIn pitches that led to demos: forget the bad, here’s the good

You’ve probably heard the constant moaning from people who’ve received bad LinkedIn DMs. But have you ever paid attention to the opposite side of that… the success stories?

For this article, I crawled through LinkedIn, fishing for posts by people who’ve sent sales DMs and booked demos without having their behinds handed to them in public (on a ceramic saucer) by angry prospects.

Narratives about LinkedIn DMs

(Feel free to skip this section) There are two schools of thought around sending LinkedIn DMs.

The smooth operators

This group believes LinkedIn is not meant for sales pitches. They advocate for long-term relationship building, i.e. commenting on prospects’ posts, posting valuable content and hoping that one day, prospects will recognise the impact of solving the problem being peddled by the salespeople.

The hard knockers

This school of thought believes that the first group’s relationship-building narrative is a waste of time.

They use LinkedIn connections and DMs as “just another touch point in an outreach sequence.” The purists of this group will hit you with a sales pitch from the get-go, forcing you to decide if you want to hear from them or not.

A few will connect, butter you up with innocent talk, and just when you’re preoccupied with rainbows and chocolate… ding! dong! They shift the conversation towards the problem their product or service solves.

In both groups, members sit on a spectrum; from extremists to moderates. (Though the extremists have the loudest of mouths on LinkedIn comments 🙂 )

Case study 1

Source: Jan Benedikt’s LinkedIn post

Study the screenshot above. Jan Benedikt, an Account Executive at fintech, Pleo, finds his ideal customer profile (ICP) on LinkedIn through tracking topics. For those of us with different methods of finding our ICPs, we might want to ignore steps 1 to 3.

From step 4, let’s look at this from the perspective of a prospect receiving a connection request from Jan.

What is going on?

Prospect sees someone who shares the same interests or industry as them, aka does not equate the connection to a sales conversation (though they may suspect otherwise based on the sender’s job title).

The seller’s hope is that they’ll probably comb through their profile, see the company they work for, and find them interesting enough to accept the connection request.

But as you work your magic on LinkedIn, you also contact them through email and try to poke a sales conversation out of them. The expectation is that the recipient will remember the previous contact with your company’s brand and that’ll make them more receptive to your follow-up cold email (a one-two punch combo).

Key takeaways

Boiled down, Jan’s success with this method shows the power of multi-touch selling. Reach out to prospects on multiple channels because you don’t know which one they’re most receptive to having a conversation on. Also, rather than going at it alone, healthy AE-SDR relationships allow for collaboration to spark conversations across multiple channels…

Case study 2

Source: Henry Clayton’s LinkedIn post

In this one, Henry Clayton, a sales rep at Refract, booked a meeting through a LinkedIn voice note. Though he didn’t give more context about his exact approach, the use of multimedia messaging when prospecting piqued my interest.

What prospecting with audio messages boils down to:

You stand out from the crowd with a voice note because few send them. Also, hearing someone’s voice in an audio or video builds trust faster compared to text… Really?

Weird study

Four researchers from the University of Michigan’s School of Information did a social experiment to study the emergence of trust among groups of people when communicating across video, audio, face-to-face and text chats.

The game was designed such that the more trust developed between the group members, the less they competed among themselves and started collaborating. And vice versa.

The results? Face-to-face communication established trust the fastest, video achieved the same level of trust as face-to-face but at a slower rate, audio was intermediate (fence sitter this one), while text communication performed the worst with group members competing against themselves throughout.

So, incorporate multimedia when prospecting, it helps—though it’ll only be as effective as your list is accurately targeted.

Key takeaways

Audiovisual content in cold outreach is not as popular, and by using it, you are more likely to stand out from other fintech sellers.

It engages prospects differently. For instance, in Henry’s case study, the prospect responded to him with a voice note, which takes less effort. You’ll see why this is important in the next case study, where the prospect was not responding despite showing interest.

Also, with audio/video, you can use your personality (if you’re lucky enough to have one 😉 ) and tone as tools to stand out. In a world of constant automation, this method could feel personal to the recipient. Try it and tell us how it works for you, and we’ll feature your story.

Case Study 3

Source: Gabi Sayah’s LinkedIn Post

Gabi Sayah’s post is more comprehensive than the first two. It’s a goldmine because Gabi used four channels; combining text, video and audio (assuming we all classify cold calls as audio).

Here’s what stands out

  • Gabi’s approach includes a trigger; his ICP needs to be searching for freelance writers to be relevant to him. Triggers are indicators of the problem your product/service solves for your ideal customer.
  • Gabi adopts a multichannel approach: LinkedIn, email, WhatsApp. It’s interesting that his prospect watches the video sent on WhatsApp but not the one on email. Maybe it landed in spam (embedding a video on the first email gets you that sometimes) or the prospect is not used to consuming video on email. People seem to have different consumption behaviours on different channels. Study how you consume content on email vs. on LinkedIn.
  • Ghosts: Gabi was ghosted twice when he took the conversion outside LinkedIn, but he had his multichannel follow up strategy to counter this. What’s yours?

Key takeaways

Measure engagement differently and attach actions

Prospects won’t always respond to your message no matter how much effort you put into your LinkedIn messaging—including the use of multimedia content.

Thus, getting a response can’t be your only measure of engagement. Track clicks on the links you send, or video watch time, then attach follow-up actions that will follow these behaviours (leaving voicemails, cold calls, emails)

To solidify this, include them in your standard operating procedures (SOPs) to ensure everyone measures engagement the right way and follows through accordingly.

Phones and warm leads

Don’t be afraid to get on the phone with leads, especially when your outreach is giving off signals that they may be interested. Reading this case study made me wonder why Gabi’s prospect agreed to a meeting after being cold-called but didn’t take action on passive outreach messages. Do you think Gabby would have booked the meeting had he not called? Tell us what you think in the comments.


Assuming you are targeting relevant prospects, selling via LinkedIn DMs will guarantee you this: some people won’t like it and will block you, others will ignore you, while a few won’t mind—but still won’t respond.

However, keep it up enough and positive responses will come. On the other hand, cold LinkedIn DMs seem not to be everyone’s cup of tea; experiment and see what fits your style.

PS: I recently witnessed an argument on a post where someone was advocating for sellers not to include a personalised note when sending LinkedIn connection requests.

“It makes prospects think you want to sell them something… they won’t accept,” he said.

Half the people in the comments disagreed, swearing on their last patches of hair that they would not accept any connection requests from anyone who didn’t take the time to personalise them.

The other half thought including a personalised connection note was creepy…. (that’s when I poured myself a cup of Kenyan tea and turned my phone off. See you in the next article.)

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Gabriel Onyango
Gabriel Onyango
[email protected]

About Me

A writer, in a marketer's skin, wearing a cold emailer's floppy socks. The unorthodox combination of these is what you've probably experienced in this blog. Freelance cold email manager; open to working with teams on cold email campaigns, copy, ICP research (snooping()and custom list building. Connect with me on LinkedIn

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