There’s a ‘Black Box’ in Your Sales Process. Here’s How to Remove It

You wouldn’t send leads through your marketing site without tracking and analytics, right? So why are you still in the dark about what happens in your sales process after your reps send a proposal? I’m sharing the two critical things SaaS sales leaders need to shine a light on to optimize your closing process.

a black box in your sales process

10 min. read

You know that having useful data is critical to making the right decisions for your sales team.

The number of leads per week, your outbound team’s cold-email open rates, the conversion rate from MQL to SQL... you know these numbers like the back of your hand, and for good reason.

Most organizations are laser-focused on the top of the sales funnel. In 2017, companies spent over $457 billion on marketing services, and the marketing automation software market is expected to grow to $14.15 billion by 2024.

But isn’t it kind of funny how organizations measure and optimize every part of the sales process except the most critical one: right before a prospect agrees to buy and hands over their money.

That’s right, I’m talking about the humble proposal, that document you send to close a deal.

Some call them agreements or contracts, but whatever you name it, most prospects expect to receive a document that outlines costs, scope, and terms. Not only that, but proposals are also a chance to reinforce the value you’ve been communicating throughout the sales cycle, and can help to persuade every stakeholder involved in the buying decision. (Yes, even the dreaded IT guy.)

Proposals are used by virtually every sales org, and yet they get very little respect.

Why is that?

Well first, let’s look at how the proposal process works in most sales teams.

A sad, but true, sales story

I was once cold-emailed about a problem I had been trying to solve for a long time (Side point: yes, outbound works.)

I jumped to schedule a demo and by the end of it, I was practically eating out of the rep’s hand.

Here’s what my sales rep says to me next:

“Sure, I’ll send over a contract for you to look at. Our ops team sends these out, so I’ll have Janice email you something over the next couple of days.”

Seemed a bit clunky, but sure.

A couple of days go by, then the weekend. Then Monday. Then Tuesday. My problem is still keeping me up, so I email my rep. He responds with, “Oh sorry, you should have received that by now. Let me go talk to Janice and ask what’s up.”

A day later, I received a DocuSign agreement in my inbox from a name I don’t recognize. Who is Janice again? It gets buried.

Now my rep is the one following up with me: “Hey Kyle, just wondering if that contract came through yet? Did you get a chance to read it over?”

I finally open the document and find a long, contract-y-looking DocuSign agreement with a lot of small-print and checkboxes for me to sign off. It doesn’t communicate the value, it doesn’t show me how it will solve my problem, and it doesn’t outline clear simple pricing. Overwhelmed, I close the document. I don’t have time for this.

What went wrong?

I’m sure you can pick apart a lot of things, but I also bet you’re now thinking about how your reps may be falling into some of the same traps.

What does your proposal process really look like?

If you’re like a lot of sales orgs, the proposal process goes like this:

  • Open email or shared drive and search for the last proposal sent.
  • Duplicate a Word or Powerpoint document.
  • Realize it’s missing content and do some more searching.
  • Eventually find a few more documents with similar content, not really knowing which is the most up-to-date.
  • Take a wild guess at one and cut-paste.
  • Formatting has shifted, so spend an hour rejigging, finding the right fonts, font-sizes and colours. (What is our corporate red again? Oh nevermind, I don’t have time, I’ll just eyeball it.)
  • Find pricing in Salesforce and manually enter it in Word.
  • Find-and-replace the company name.
  • Finally, export as PDF, attach to an email and move on to the next prospect.

I’m sure as you read that you thought: This isn’t right.

But that’s what practically everyone does!

It’s how most companies’ proposal process ends up looking something like this:

an example of a messy sales process

This approach is prone to all sorts of costly errors:

  • Errors in pricing (Did they forget to type a zero?)
  • Errors in spelling (Who is [COMPANY]?)
  • Inconsistency in branding (Would your CMO shed a tear if they saw what went out?)
  • Inconsistency in content (Why are we using a case study from five years ago?)

This makes your company look unprofessional. At best, the prospect thinks you don’t have your stuff together. At worst, it can cost you the damn deal.

Enter the proposal ‘black box’

Okay, say your rep finally gets a proposal out to their prospect. So what happens next?

Your rep does their usual follow-up sequence: “Hey, just wondering if you got a chance to read that proposal I sent over last week. Let me know if you want to hop on a call.”

Since your team sends a PDF, your reps are flying blind here. They (and you!) have no visibility into how the prospect interacted with it. You might be able to see if they opened the email or maybe even the document, but that doesn’t tell you much.

You still don’t know key details like:

  • Did the prospect read it?
  • Did they just skip down to pricing?
  • Did they open it for 10 seconds and then close it because they were confused?
  • Did they come back to it multiple times?
  • Did they forward it to a colleague, the person who actually holds the purse strings (despite the prospect assuring you he is the final decision maker)?

It’s all a black box. You have no idea how the prospect is interacting with the proposal.

You don’t know what you don’t know

You got lucky and your prospect read the proposal. What else are you still in the dark about?

Let’s say your sales rep has changes to make to the document. The prospect has asked for a discount. Is this rep allowed to discount? By how much? Oh, and the prospect wants to do quarterly payments and they wish to pay by cheque. Can the rep go ahead and make those changes to the deal’s terms and conditions?

Now the rep is engaged in a game of back-and-forth negotiations, and they may or may not be following an approval process. Some rogue sales reps could be making changes to pricing and terms just to get the deal closed—even though they’re bad deals that leave money on the table and lock your company into long-term contracts.

Not to mention your poor sales ops and finance team are left wondering why the pricing in Salesforce isn’t getting reflected in the accounting reports to upper management.

It’s a huge headache.

Taking back your proposal process

When you see it written out in agonizing detail like this, you probably think that it’s insane that we are still doing things like this in the 21st century.

All of the lead gen activities and demos don’t make a lick of difference if deals are getting stalled during the back half of the sales cycle. An unpredictable closing process is costing you real dollars in lost deals, delayed deals, or just plain bad deals.

OK, but what can you do about it?

There are two key elements you need: control and visibility.


Your reps are running wild in the streets at the most crucial part of the sales process. Of course, you don’t want to do the work for them. You just want to put some guardrails in place.

You want to make it easy for reps to send out professional, accurate, on-brand proposals with consistent content, pricing and terms, and without a ton of messy copy-paste or time-consuming manual entry.

And frankly, wouldn’t that just be better for everybody?

It’s better for reps who can spend more time talking to prospects and less time trying to figure out what line-height goes best with 12px Georgia font.

It’s better for prospects who can have their problem solved faster.

And it’s really better for sales leaders like you, who can run tighter, more predictable cycles, and increase your deal sizes.


A tighter process means better visibility into where deals are getting stuck, and what content is getting read and what’s not, so you can actually optimize it. It’s removing the black box from your closing process.

Just think: You wouldn’t send leads to a marketing site without analytics, so why would you send prospects to a proposal without advanced monitoring and reporting?

OK, so how do we actually fix this?

To get control over the process and send consistent, error-free documents, you need three things:

  1. An on-brand templated proposal document.
  2. A proposal creation workflow that actually works.
  3. A way to get insight into what is happening with your proposals once your team sends them.

1. A modern, professional document template

You should have your marketing team or hired experts build a well-designed, well-written, on-brand template that makes prospects stop in their tracks.

a colourfully modern proposal template

But more than just a great looking document, your proposal should also be modern in how it’s delivered. It should be web-based and interactive. Why?

  • 25% of potential customers first interact with a SaaS proposal on a mobile device. [source]
  • SaaS proposals with interactive pricing are 173% more likely to close than proposals with static pricing.
  • Adding video to your proposal improves the close rate by 41%.
  • Proposals with forms close 65% faster than those without.
  • Proposals with electronic signatures are 2.5x more likely to close than those without.
  • Using a payment integration to secure deposits ups close rates by 44%.

Sticking to Word and PDF is a missed opportunity to truly engage and convert prospects to buyers.

2. A solid proposal creation workflow

A template strategy ensures that reps don’t have to start from scratch every time, as they have an established starting point with placeholders and pre-defined sections to fill in.

It also means documents are consistent. You can make universal edits and know that all future proposals will be created using the most up-to-date version.

What is involved in this kind of control?

  • All data from the CRM (contact info, pricing, dates, etc.) should be automatically mapped into the documents so there is no manual entry.
  • You should use a content management strategy so that reps can find modular bits of text, images, and pricing they can drag-and-drop into a document.
  • Granular permissions so reps can use (but not edit) certain sections of the document and they can’t mess up the branding.
  • A guided workflow so that reps who tend to go rogue need approval before sending.

3. Proposal insights and metrics

Did you know 55% of SaaS proposals are created and sent within 30 minutes and that, on average, winning proposals are viewed 2.5 times before they’re signed?

Probably not, because your current process likely isn’t measurable. You can’t manage what you don’t measure. And you can’t optimize anything if you don’t have the data, like:

  • Has the prospect not even opened the proposal yet? That should automatically trigger a reminder email from the rep.
  • Is the prospect reading the proposal right now? That’s a great opportunity for the rep to reach out while it’s top-of-mind.
  • How long are prospects spending on each section of your proposal? You need to understand how prospects are interacting with your proposals and find out what could be costing you a quicker close.
a snapshot of our software proposal analytics

Can you achieve this with your status-quo software?

Word, Box, DocuSign, CPQ—all great for what they do. But they aren’t enough to tackle the proposal problems I outlined above.

You need specialized software that gives you tighter control over and visibility into your closing process.

You need software like Proposify, the secret weapon for over 10,000 successful sales teams around the world and has been rated in the top 6 of all products for sales.

One of our customers is Mike Watson, the sales director at Orlo, a SaaS company in the social media space. He had this to say:

“Six months ago, we were doing an average of about $3,500 ARR per deal, and it’s now up to $12,000. Proposify made it possible to streamline our proposal process and triple our average deal size.

The other reason I use Proposify is to monitor deals. We might be having 10 to 15 a month. I need to go back in and do my metrics for that period. So, I’ll use Proposify to reconcile the actual signed contract with what the guys have forecasted in Pipedrive. I know that whatever is signed off in Proposify is the actual contract value. That gives me comfort that the numbers all align.

I’ve got full visibility of any deal that’s created in Proposify and integrated into Pipedrive.”

Would you like to get that kind of visibility? Request a demo to learn more about how Proposify can help.

There’s a ‘Black Box’ in Your Sales Process. Here’s How to Remove It

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