Article on Overloop the sales engagement, cold email, and LinkedIn automation software

What is Overloop?

Overloop is a Sales Engagement Platform.
Send ultra-personalized multi-channel outbound campaigns mixing cold emails, LinkedIn automation and phone calls.

Learn more...

48% of Salespeople Will Never Do Any of This

Forster Perelsztejn author on Overloop the sales engagement, cold email, and LinkedIn automation software blog
Forster Perelsztejn Sep 14, 201710 min read

This is not the first time we talk about the importance of following up on this blog.

Grant Cardone will tell you to be unreasonable about it. I won't, because you can actually be sued, in a criminal court, if you keep spamming your prospect's devices and sending them packages after they said a couple times that they're not interested.

He doesn't really care about that, he will even tell you that driving too fast and getting speeding tickets are a good thing. I tend to believe they're just reckless driving and endangerment of people's lives but hey, what do I know?

But if you're real about selling anything, you need to be relentless about following up with every prospect.

But how should you do that depending on the context?

Read on, I've got a few ideas for you.

[alert type="warning" icon-size="normal"]Want to keep them handy? Download the templates now! [/alert]

1. Follow-up after trial

Subject: {{prospect_firstname}}, what did you think of your trial?

Hey {{prospect_firstname}},

Your trial just ended, I hope you enjoyed it!

Is [PRODUCT NAME] a good fit for your needs? What made you go 'Wow!'? What made you go 'Ugh!'?

I'd like to know all about it :)



PS: If you would just like to pick up where you left off, please follow this link to our paid plan!

In what circumstances should you use it?

  • Your prospect just tried your product for a determined amount of time
  • You want to get them to opt for a paid plan

Why it’s good:

  • You’re not just informing them about the end of their trial
  • You’re asking for feedback, which at least puts you ahead of the rest, even if you don’t sell. Plus, they only need to hit the reply button
  • You’re not pushing them too hard towards the paid plan but you provide a clear call to action in the PS

Tobin Lehman at New North insists that the sales of a SaaS depends on a great follow-up. This article by Neil Patel at Kissmetrics highlights the fact that you should push prospects down the funnel by encouraging them to take action, any action. Asking them to provide feedback or simply having them reply to an email could tip the scales in your favor. Just make it easy for your prospect to do whatever you want them to do.

2. Follow-up after show of interest

Too many salespeople keep “just checking in”, “touching base”, “dropping by”…

Don't ever do that.

It makes you come across as shy and unfocused. If your job is to make the sales easy for the prospect, you should be asking where the situation’s at and how they’d like to move further.

Subject: Hey {{prospect_firstname}}, what next?

Hi {{prospect_firstname}},

I'm following up on our conversation about [INSERT YOUR PRODUCT NAME].

We at {{user_company_name}} are really excited about working with you! What do you suggest as the next step, if any?

Thanks in advance,


In what circumstances should you use it?

  • You already had a productive contact with your prospect
  • They have shown interest in one way or another

Why it’s good:

  • You’re not “just checking in”, which is the biggest mistake salespeople do when following up
  • You’re giving the prospect ownership of the process, which is more likely to make them move forward

These are the numbers our sales guys gets from follow-up campaigns using this approach after demoing our product to prospects:

These look like exceptional numbers but since those are prospects who showed interest after finding us instead of us finding them, it starts to make sense. Also, they got a demo of the product, which got them familiarized with it and with our sales team. Bottomline, we’ve been getting 53% of prospects who replied to sign-up after getting this email (and after having been shown around the product).

3. Follow-up after cancellation

Subject: {{prospect_firstname}}, what would have changed your mind?

Hi {{prospect_firstname}},

I just saw that you decided not to move forward with us. I understand if this isn’t a good fit and wish you the best of luck in your future endeavors.

You probably have a lot on your plate but if you can find a minute to tell me about two or three things that could’ve changed your mind, I’ll really appreciate it.

We’re always trying to improve and would really appreciate the feedback.



In what circumstances should you use it?

  • Your customer canceled their account/subscription

Why it’s good:

This one comes from Michael Pici, director of sales at Hubspot. He shared it because it worked on him. As a seasoned salesman, he managed to identify what made that email so good:

  • It plays upon his desire to help; it’s hard to reject that kind of request when someone is trying to get better at what they do.
  • It’s easy, the answer can be formulated in less than five minutes, which is crucial.
  • It felt genuine
  • Most importantly: it make him think about the product why he actually walked away from it. And when he typed them out, his reasons didn’t seem that compelling anymore.

He ended up buying.

It doesn’t mean that it’ll always work but if you at least get feedback from it, it’ll still be better than 99% of breakup emails out there.

4. The long run

If you can't convince your prospect do to business with you in the short term, you must keep nurturing the relationship.

According to sales expert Anthony Iannarino:

If you aren’t nurturing your dream clients over time, then you cannot expect to be known for the value you create when you finally have the opportunity to ask for meeting.

This made me think of you

If you come across a piece of content (blog post, infographic, video…) that you think might interest them, just forward it to them and, if possible, spark a discussion.

It doesn't even have to be business-related. Is your prospect a big fan of The Killers? Tell them you remember and ask what they think about the new album. Are they going to the show?

Be my VIP

Are you organizing an event? Good, invite them as a VIP. If you think they could bring something to it, ask them to be a guest speaker.

Asking for favors actually makes you likable. This technique was well used by United States founding father Ben Franklin in order to bring a rival legislator to his side.

As Charlie Liang would say, it's not about making mini-minions out of everyone around you but leveraging empathy!

Happy birthday!

Who doesn't like to be wished a happy birthday? Don't be a stalker about it, but if your prospect's birthday is easily accessible to you -through LinkedIn for example- put a reminder in your calendar and send them a personalized email! How many of their business partners actually take the time so wish them a happy one?

[alert type="warning" icon-size="normal"]Want to keep them handy? Download the templates now! [/alert]

 Sky's the limit

According to David Freedman from Huthwaite:

An Advance is when a customer commits to take action that moves the sale forward by providing access to a new, meaningful resource.

Your follow-up efforts should be focusing on getting the prospect to take an advance. You will rarely ever close a sale during the first or second interaction, but you should get your prospect to take action -even small things- that move the process forward.

Would you travel half the world to attend a conference? All that starting from a single email? With your spouse and all expenses on you?

Well, Dylis Guyan has. How did that happen? She tells the story in an interview with John Smibert:

About 10 years ago I was asked to a conference in America by email. Now, that would’ve cost me a flight, it would’ve cost me a hotel and everything else; there’s no way that I would’ve said yes to that just from one email. But that was then followed up with another email, I then got a direct mail piece, a letter, then I got a postcard, and then I got a phone call, and each time I had that contact from the company, it sort of made me lean forward, because it was all about the benefits to me and how I could grow my business by attending this conference. In the end, ~in that six~ contact, I made the decision to go; in fact, myself and my husband went, so we paid for two flights and all of the associated costs.

You decide where to set the bar in terms of number steps and creativity.

As long as you don't turn it into harassment, persistence is key!