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Dropbox Docsend
Dropbox DocSend
February 16, 2023
How to tailor your follow-up strategy to close more deals in less time

Ah, the sales follow-up strategy—so essential, yet so easy to get wrong.

The great thing about working in sales is that you know what it’s like to be a prospect. But that means you also know what it’s like to get follow-ups that annoy you, even as someone who does sales

Sales follow-ups can feel like a catch-22. You know deals require several touch points before they close, but you don’t want to be aggressive with your follow-ups. So how do you get the sales follow-up right?

We’ve gathered advice from sales experts on new ways to follow-up with prospects, none of which involve annoying them. Keep reading to find out how to use a combination of old-fashioned emotional intelligence and new technology to rescue your follow-up strategy from the closed-lost graveyard.

First: Do you understand your sales cycle?

We could tell you such-and-such study found it takes four or five or six follow-ups on average to close a deal—but it wouldn’t help you with your follow-up strategy. 

This is because sales cycles—how long it takes, on average, for your prospects to buy your product or service—can vary a lot by company. The general rule of thumb is that the higher the cost of the product, the longer it takes to sell.

But you won’t truly understand your sales cycle until you pick through its history with a fine-toothed comb. This is the first step to building your follow-up strategy, because you won’t be able to design a touch point cadence until you know how long prospects engage with your sales team. 

Here’s where detailed analytics on all your sales material can help. Before you draft your follow-up strategy, use historical data to answer these questions:

How long does it take my sales team to close a deal?

To calculate your sales cycle, start by using the data in your CRM (like Salesforce or Hubspot). 

Choose a period of time — usually the same period your company uses to report revenue — and see how many deals you won in that period. For each deal, track the number of days it took to close the deal from when it was first created. Add up all those days, then divide by the number of closed deals. 

For example, if you closed 125 deals in Q3 and the total number of days it took to close those deals combined was 3000, then your sales cycle would be 3000 / 125 = 24 days.

Which milestones trigger my prospects’ decision to buy?

It may be tempting to take the easy road and schedule your follow-up cadence based on your sales cycle alone. But the reality is that humans don’t make decisions on a schedule. They make decisions based on emotion. 

If you lead a sales team, gather your reps together and ask them what triggered their last five prospects to buy your product. Encourage your reps to go deep on emotional needs, and keep asking why until you’re satisfied with the depth of their answers.

When you’ve gathered enough reasons, you’ll start to notice patterns. Map those reasons to milestones, and let that form the foundation of your follow-up strategy.

Who’sactuallyreviewing my sales material?

The higher the product or service costs, the more decision makers will be involved in the sales process. But what happens more often than not is that sales reps will pitch the product, then their materials are shared with the actual decision maker after the fact. 

A secure file portal like DocSend lets you see the email addresses of decision makers who review your material. This information can radically change your follow-up strategy, so that you’re talking to the right person a lot sooner. 

How long are people looking at my sales material?

Lead qualification is the backbone of any efficient follow-up strategy, so you’re spending time and resources on the right prospects. 

A secure file sharing platform with robust engagement analytics can tell you exactly where to spend time following up. Build follow-up strategies for prospects who:

  • Spend more time reading documents

  • Watch video pitches from start to finish

  • Reply after reading certain documents over others

After a quantitative and qualitative analysis of your sales cycle and prospect engagement, you’re ready to build your follow-up strategy. Here’s some expert advice on novel ways to do it:

Ask prospects to tell you more about their problems

It seems almost too easy, but as sales expert Andy Paul says, “Too many sellers just plow through their usual list of questions. They're anxious to tick all the boxes for the information they've been told to gather.”

When you lead with curiosity in your follow-up, you’re achieving two goals in one: showing the prospect you care while gathering more information about emotional drivers to buy. 

In your first conversation with a prospect, practice deep listening and take notes. Then, “follow the pain”—follow up with a question about the most salient pain point from the original call. You’d be surprised how many people want to talk more about what bothers them. 

Involve your existing customers in your follow-up strategy

You may need to lean on incentives to make this work, but sales leadership coach Kevin Dorsey believes it’s worth it:

What’s more powerful than a pitch from a sales rep? A customer testimonial, every time. Involve your customers as much as you can in your follow-up strategy, and you may even end up shortening your sales cycle over time. 

Use video to get attention from prospects

When emails and phone calls aren’t working, try using personalized video recordings to stand out. Video is quickly becoming a must for sales reps, with 26% of deals closing faster with proposals driven by video.

Follow-up videos can include:

  • An expansion on one part of your pitch that’s seeing high engagement

  • A quick tutorial for highly engaged prospects with a specific problem

  • A customer testimonial

Bonus points if you can record video from the same file sharing platform that houses your sales material. For example, with DocSend’s integration with Dropbox Capture, you can create video pitches, share them, and see how they perform, all in one place. This way, you can switch up your video follow-up strategy quickly if the analytics show you need to. 

Start social selling to prospects

When email, phone calls, and video aren’t cutting it, incorporate LinkedIn in your follow-up strategy. 

Social selling on LinkedIn requires a delicate approach. People don’t go to LinkedIn to be sold to, so you want to engage with warm leads only. 

Make it easy for prospects to view your materials

Ease of use, removing friction, etc. — we apply these principles to products, so why not the selling process?

A long sales cycle involves a lot of documentation: pitches, proposals, video tutorials, statements of work, contracts, etc. What this often translates to is searching email to find the files you need, both on the sales side and the prospect side. 

Customized virtual data rooms (VDRs) strip away this friction and make all files accessible with just one click. Sales reps have found that they’re able to improve client relationships with an organized data room that doesn’t force the prospect to download software or create an account.

When you execute your follow-up strategy, you’ll be sending your prospects to the same place every time: a digital space, customized with your logo and theirs, that has all the documentation they need to make a decision that much faster. 

Want to use a secure file sharing platform to build a better follow-up strategy? You can access DocSend’s virtual data room by starting a free trial. Virtual data rooms are part of the DocSend Standard plan for $45 per month per user.

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