PLG sales: How the best reps book meetings and convert free users into paid users

by Frederic Melanson in ,
Blog cover tricks to convert more users - Bliinx

The fastest-growing product-let businesses convert on average 27% of their free users into customers!

Seems freaking high, doesn't it?

If you're at that number, I got nothing to teach you today. Go on with your life.

If you're below that number; care to learn a few tricks?

I've interviewed growth leaders at high-growth SaaS like Loom, Lemlist and Pitch.

They all have a few things in common:

They engage users where they live (digitally, let's not be creepy).
They connect with their users.
They act as partners, not vendors.
They hyper-personalize.

Allow me to explain and give you concrete examples 👇

1- Booking more meetings by engaging where your users work 🗓️

Unsolicited phone calls will scare prospects away.

Instead, engage them where they work.

Try text messages, LinkedIn messages and in-app messages.

Also, approach the conversation from a help standpoint rather than pitching.

From Kate Taylor @Notion:

“Self-serve isn’t about competing with sales, it’s about creating a healthier funnel. There are tradeoffs and tensions along the way, but you need to stay the course.”

Of course, help will mean a paid version for you. But the customers’ experience will be much nicer with this mindset!

*Zoominfo’s AEs call prospects within 60 seconds of free sign-up, so it obviously depends on what works for your customers.

Here are examples from, Applinks and Lemlist 👇

Using text messages to book meetings:

Text message user outreach by reply io

Using chatbots to engage leads in conversations:

Chatbot help conversation
Chatbot help meeting request

Neat trick from Lemlist's founder:

Use a phantom to make your founder's or sales reps’ LinkedIn account automatically send connection requests to users on LinkedIn.

Phantom buster examples auto-connect LinkedIn

If they accept, you can send them a message to engage in a sales conversation. 

Send the message later, though!

Sending a message right after a request is annoying and salesy.

And no one likes it.🙅

2 - Upgrading accounts with the consultancy approach 🧑‍🏫

You have to work alongside your users.

Communicate to them that you truly understand their reality and that you’re here to help.

To do that, you can build a sales engagement strategy with hyper-personalization.

The idea is NOT to focus on the volume of your touchpoints, but rather on quality.

By quality, I mean:

1. Timing of your reach out (most important, in my opinion).

2. Value added by your reach out.

3. Personalization & relatability of your message.

Here’s a great example of personalized empathy and timing from Unstack.

unstack onboarding emails

See what they did here? (don’t know if it was intentional or not).

They saw that I was starting to use their blog functionality a lot, thus prompting me with helpful content!


A follow-up email to talk about a premium blog feature would work 100% well in this context.

At least for me! 

3 - Use onboarding data to personalize your sales touchpoints 🎯

As a product-led sales rep, you have an advantage over other businesses.

👉 People tell you about them before you engage.

It’s a great advantage for self-serve businesses. You don’t make revenue upfront, but you know key information about your prospects.

That's a sales reps' dream.

If your onboarding is great, you will have data about your prospects.


Their position/role.
What they’re interested in doing with your
The size of their business.
The technology that they use.

With that information, you can craft a better experience and know when/how/with what to engage users.

The example from Unstack’s email (picture from the section above) is a great example of that.

They knew from onboarding questions that I’m a founder who’s also running marketing campaigns.

They combined that knowledge with my increasing usage of the blog feature to send me some content on blog publishing.

Here's another one from Hugo's tech touch (more examples and details in our complete guide to PLG Sales ebook):

Hugo tech touch email working on weekends

The relevancy is awesome.

It makes you love the brand even more and totally open to a sales conversation.

That's all for today, folks!

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Have a wonderful day :)


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