Sales Documents: 5 Ways to Add Time-Saving Automation to Your Workflow

I talk to many sales leaders. And they all say the same thing: Why are sales documents so difficult for my sales reps to put together? But it doesn’t have to be this way for you. Here are my top five ways to save time AND create better sales docs by optimizing your content collateral workflows throughout your sales funnel.

how to automate you sales document workflow

6 min. read

I've had a lot of sales leaders reach out to me recently about how frustrated they are with the way their reps are putting documents together.

For a lot of companies, sales documents are such an important piece of the sales cycle. You have everything from sell sheets and case studies to proposals, order forms, quotes, and contracts. They're all required to get a deal done.

But it's freaking hard to put this stuff together.

And the reason why it's so hard is that none of the tools you're using to put these documents together is integrated within your sales workflows. There are multiple steps, tools, and people involved at every stage.

It doesn’t have to be this way.

Too many sales doc touchpoints, so little time

When it comes to sales reps, sales documents require too many administrative tasks.

For example, I was speaking with one of our Proposify customers recently. They said that when they first started with their proposals and contracts, each proposal took 40 steps to complete, from creation to receiving the signature from their client and closing the deal.

That's way too much work to put into a document. And, as everybody knows, time is money.

The longer it takes to put a document together, the more reps are spending time on non-core-selling activities. They either have to sneak into their golden hours or spend nights and weekends slapping stuff together, which can put a strain on their personal relationships.

Plus, if it takes too long for reps to put stuff together, they might take shortcuts and not put the right amount of effort required to get something compelling out to customers. That reflects very poorly on your company.

But not only that, time kills deals.

If you're waiting too long to put a document together and it takes you two weeks to get it out, your competitor might sweep in ahead of you because they have a better, more automated sales cycle. And, all of a sudden, you're losing the deal.

My top 5 areas for sales document automation

No one wants to lose a deal like this, because a solution is within your control.

So, here are five vital areas where you can add automation to your sales process workflows to alleviate some of the biggest challenges around sales doc creation.

1. Document creation

The first one is automating the creation of your sales documents. If you're still using Word, PDFs, PowerPoint, and those kind of programs to put documents together to send out to prospects, then you know what?

You're a dinosaur.

There are many tools that integrate with your CRM now that can pull the right information together to get a document started at different stages of your sales opportunities.

If you're not using that kind of document automation in this day and age, you're really not a modern sales team. You have to look at your tech stack in general for ways to make your document creation more effective.

Like starting a new proposal or quote based on hitting a stage in your CRM.

Or pulling important client information into your document at scale.

Or dragging and dropping relevant content into the right areas.

All of this can be automated. There should be no time-wasting copy/pasting anymore.

2. Searching for relevant sales content

This brings us to the second piece, which is your sales content library.

A lot of reps, when they talk to me, are copy-pasting case studies and snippets of documents from all sorts of different places, either saved in a Google drive somewhere or a SharePoint.

They might be taking something from Slack, asking their colleagues to send their latest proposal or presentation, slapping some stuff together, and piecemealing a Franken-presentation or a Franken-proposal.

It creates a time-consuming process to put together something that ends up being less than mediocre.

So, it's really important to have a content library that's well sorted, where you can go in and search, pulling the right information at the right time. A central place where reps know exactly where to go to find what they need.

Your process and library organization should also automatically tell salespeople, "Hey, this is what you should put here so that it makes the whole process way more effective."

3. CRM data entry

The third one is data entry.

Your CRM is important. It's important to document everything in there. After all, that's how managers keep track of how deals are going and forecast their pipeline.

But nobody likes to do it. The actual act of data entry is pretty tedious from a rep perspective.

Adding automation can provide a two-way flow of data between your CRM and your sales document software. For example, you could integrate a tool like Proposify with your CRM, such as Salesforce or Hubspot, to add automation for better contact and pipeline management.

These apps can use deal milestones, like the documents that your sales team sends out and the interactions your prospects have with them, to update your CRM in real-time and move the deal stages forward automatically.

4. Document notifications and tracking

The fourth piece is your notifications.

Let's say there’s a deal that's $500 MRR. You don't want your reps to spend too much time chasing these smaller deals, but a handful every month can really help get a rep above quota.

You can add automation on the documents when you send them out using Yesware, SalesLoft, or another app with document tracking capabilities. Your reps then get notified about any interactions within those documents.

They can use that interaction as a way to track and follow up with prospects at the right time so your reps are not spending time chasing stuff that's gone completely dark.

5. Sign-off

And the last piece is the signature process. There are lots of cool sales tools out there that use legally-binding esignatures to speed up sign-off.

Automating signatures is a really quick way to get a win. When you have an order form in front of a hot prospect and the signature box is right there at the bottom, all they need to do click a button and boom, it's done.


Adding automation in all these areas helps with getting deals moving forward way faster and I'd love to get your feedback on this.

What are the ways you're automating the document creation process? How are you automating your sales process workflows within your entire cycle?

How are you leveraging documents throughout? What are some areas where you feel like your reps are struggling a bit, and what are some ideas that you can put in place to help automate the process so your reps are more efficient at closing deals?

Let's start a conversation—please leave a comment below or connect with me on LinkedIn.

Sales Documents: 5 Ways to Add Time-Saving Automation to Your Workflow

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