Closing Time

The 4 Keys to Creating Successful Sales Proposals

What’s in between a ‘yes’ and a signed deal? The sales proposal.

The proposal is an opportunity to cement the deal or possibly lead it astray, so it’s crucial that salespeople get it right. 

In this episode of Closing Time, Insightly’s Chip House is joined by Keith Rabkin, CRO at PandaDoc, an e-sign software for businesses. With more than 50,000 customers, the team at PandaDoc has some insights into what works – and what doesn’t – when it comes to proposals. 

Keith and Chip talk through the 4 keys to successful sales proposals (timing, format, customer focus, and analytics) that are proven to better engage customers and increase close rates.

Watch the video:
Key Moments:
1. Sales Proposal Timing

When it comes to sending a sales proposal, timing is crucial. PandaDoc data shows that proposals sent on Fridays or weekends actually have a higher chance of closing. .

Why? Keith’s hypothesis is that the end of the week is when people have more mental bandwidth and are less distracted by the tasks that pile up during the workweek. Proposals require time and focus to understand, and customers are more likely to give that attention towards the end of the week.

It’s important to note that following up with customers towards the end of the week is also crucial to close more deals. This is when customers are most likely to make a decision, and a timely follow-up can help seal the deal.

2. Sales Proposal Format

The format of a sales proposal is crucial to winning business and standing out from the competition. The ability to add images and videos to a proposal can help evoke emotions and create a professional and memorable impression on potential customers.

It doesn’t matter if you’re a small business or a large enterprise; the look of the proposal and the engagement of potential customers will impact close rates. PandaDoc data shows that including at least one image or video can significantly increase the chances of closing the deal, and proposals with photos and videos close at 32% better rates than those without.

However, it’s crucial to strike a balance between text and imagery, and the ideal proposal size for high close rates is 6 to 8 pages. Proposals longer than that risk diluting the message, while shorter ones don’t have enough to differentiate the business and its offerings.

Using a professionally crafted proposal with appropriate imagery and formatting can signal professionalism and differentiate your business from the competition. Proposals created in Google Docs or Microsoft Word may not appear professional and could impact potential customers’ impression of the business.

3. Sales Proposal Customer Focus

The importance of personalizing and customizing sales proposals cannot be overstated. Customers are more likely to respond favorably to proposals that are tailored to their specific needs and use cases.

While it’s not practical to craft every proposal from scratch, sales teams can use integrations and customer data to customize proposals and ensure they are customer-focused. Proposals that convey the value of the software and address the needs of the customer are more likely to result in a higher close rate than generic proposals. This is similar to the concept of customized cold outreach, where personalized and tailored communication performs better.

Here are ways you can personalize your sales proposals:

1. Highlight the specific needs and pain points of the customer in the proposal.

2. Address the customer by name and use their company’s logo or branding in the proposal.

3. Tailor the pricing and terms to fit the customer’s budget and preferences.

4. Customize the proposal with specific product or service features that match the customer’s requirements.

5. Incorporate customer testimonials or reviews to build trust and credibility.

6. Offer a free trial or consultation to help the customer make an informed decision.

7. Provide a clear and concise summary of the proposal that highlights the benefits and ROI for the customer.


4. Sales Proposal Analytics

With modern e-sign platforms like PandaDoc, salespeople have the ability to send proposals electronically and use analytics to see if the potential customer has engaged with them.

By analyzing how much time customers spend on each page of a proposal, what links they click, and whether they downloaded it, salespeople can determine the level of interest and prioritize their next actions. They can also run tests on different pages of the proposal and swap them out based on the analytics, much like an AB test on a website.

Here are a few examples of salespeople using analytics to influence outreach:

1. You notice that a prospect has spent a lot of time on the pricing table, but has not yet made a decision to purchase. Using this information, you can reach out to the prospect with a tailored message asking if they need any help with understanding the pricing or if there are any questions you can answer.

2. You see that a prospect has forwarded the proposal to several people within their organization. This indicates that there may be more interest than initially thought. You can then reach out to the prospect with a follow-up message, offering to schedule a call to discuss the proposal and answer any questions from the team.

3. You notice that a prospect has not yet opened the proposal, despite it being sent several days ago. Using this information, you can send a reminder email with a personalized message, asking if there are any questions you can answer or if there is anything else you can provide to help the prospect make a decision.

By using this data to tailor outreach, you can drive a much tighter engagement with the prospect. The insights provided by sales proposal analytics make salespeople look smarter and more professional, providing them with valuable data about their prospect’s engagement and interests. 

Where to Put the Master Services Agreement

When it comes to larger deals or enterprise deals, there may be a master services agreement (MSA) involved. So, where should the MSA be included in a sales proposal?

One suggestion is to append it at the end of the proposal, but clearly differentiate it from the rest of the proposal by using a separator slide. This way, the decision maker can focus on the important parts of the MSA, while also being able to easily access it if they want to read it. Certain tools, like PandaDoc, allow you to point people to specific parts of the document, which can be useful for directing your lawyer’s attention to the MSA.

Including the MSA at the end of the proposal allows the proposal to serve as an appealing UI for the rest of the information being sent to the customer, while still providing access to the necessary legal information.


You’ve gotten the customer to say yes, and it’s time to send over that proposal. Let’s dive into the four keys to making it a successful one in this episode of Closing Time. Thanks for tuning in to Closing Time the show for go to market leaders. I’m Chip House CMO at Insightly CRM and I’m joined today by Keith Rabkin, CRO at PandaDoc. And previously with brands like Google, YouTube and Adobe. Welcome to the show, Keith.. Thanks for having me. I’m really excited to be here today. Yeah, it’s exciting to have you. And you and I were able to connect before and talk about the immense dataset that you have. So with more than 50,000 customers, your team at PandaDoc has some insights into what works, what doesn’t when it comes to proposals. And, you know, generally those that watch and listen to Closing Time, are sales leaders, go to market leaders, and they would really love to kind of get your insights into, hey, why are we sending proposals anyway in the first place? Yeah, I’m happy to share some of what we’ve learned over the years that we’ve been in business. I just joined pretty recently but have been amazed by the wealth of information that PandaDoc has. Proposals, contracts and quotes are our bread and butter, so we learn a lot about what works and how the best proposals can be differentiated. And so I’m happy to share some of that. It’s like an incredibly important part of our business because that sales piece is so crucial to what we do. Yeah, no question. You know, and by the way, so Insightly is a customer,. I’ve been a customer in a previous life. I’ve built proposals in PandaDoc, very cool software. And, I know that you have a model and you talk about, the four keys or best practices about proposals and they include timing, format, customer focus and analytics. So maybe let’s start out with what’s the appropriate timing to send a sales proposal? Yeah, absolutely. So of course, most people realize that the best time to send out proposals is during the workweek. But surprisingly, we found that most proposals will actually close on Friday or the weekend more than any other day of the week. So it’s really important to get those proposals out. But just know that you’re going to want to follow up with them close to the end of the week when customers are more likely to close. Why do you think that is? So people are more likely to close. Thursday, Friday and the weekend also. Yeah, I think it’s when people have the time to deep dive into the details of the proposal. So we’re all so busy during the workweek and we’ve got a lot of things we’re trying to get done. And proposals require this like thought processing and this way of understanding what’s in the proposal. And I find that you see that clear up towards the end of the week and you get more mindshare to actually go through and make the decision. And that’s my hypothesis of why. Friday and the weekend perform better. But we definitely see it with our data, Friday and the weekend, more deals close than earlier in the week. It makes a ton of sense and that’s what I know built into PandaDoc you can format a proposal, right? You can add images, you can add a pricing table, you can bring in video. You know, and so especially in today’s buying age, you have multiple buyers or multiple influencers inside of an organization you’re trying to influence. So that ability to forward it on, I think the format becomes super important. You know, our sales team leverages the Insightly integration with PandaDoc that I think we’ve had in place for about five years. But talk to me more about format, and why is it better to to send that kind of proposal that’s well, I don’t know, in a way, pretty? But also. you know, functional and the type of document that you can brand it versus just sending a word document. Yeah. If you think about it, what are you trying to do with the proposal? You’re trying to win business and you’re going to win more business versus competition when you stand out. It doesn’t matter if you’re an SMB when you’re competing against smaller firms, but there are a lot of them, or you’re an enterprise, you’ve invested a ton of money in your brand at the enterprise scale and at the SMB level you have a brand you’re probably very proud of and that you think differentiates you. So when you get a proposal, how it looks, what kind of emotions it evokes in you, those are things that are going to matter to the person who’s digesting it. So I think being able to stand out with photo, video, and the formatting is absolutely crucial, whether you’re a small business or a larger business. How you do that, what kind of photos and media you include depends a lot on what kind of a business you are, and you’re going to want to tailor that. We generally recommend at least one image or one video to help you stand out. And what we find is that when you include a photo and video in your proposal, they close at 32% better than those that don’t have it. So that’s absolutely important and drives success from a sales engine side. I think the other side of it is on the length. And of course this also matters based on the industry you’re in. The ideal size we find for high close rates is 6 to 8 pages and those do convert better than others. Any longer than that means that your message is getting diluted. But any shorter than that means that you don’t have enough to differentiate your business and what you do. So you’re gonna want to make sure that you have that length correct and that you balance text efficiency with imagery. You can tell when something’s made in Google Docs or Microsoft Word, and it doesn’t necessarily signal professional in the way that an amazing, beautifully crafted proposal will. It’s funny because I buy a lot of software, too, and so people will send me. PandaDocs to sign. And I’m always, you know,. I click on the link semi excited to see what their proposal is going to look like. And sometimes I’m disappointed and sometimes I’m blown away. Right. But it’s I mean, as a brand, you’ve built this phenomenal looking brand probably and all the messaging around it and it’s your chance as a marketer to give your sales team a chance to reinforce that. The other thing that I was thinking about as you were talking, Keith, is, you know, what’s your choice as a salesperson if you’re not going to use something like a PandaDoc to send the proposal, you might send a Word Doc and maybe a PDF or a PowerPoint. And that’s kind of harder for the customer, I would think, to deal with, and it’s not as friendly to forward on inside of an organization. So I don’t know if that’s what you mean by customer focus, but you bring customer focus into the equation here. What does that mean, adding customer focus to your proposals? Yeah, So customer focus really is about making sure that the proposal is specific to the type of customer that you’re going after. And so when I think about the use cases we have and that we sell to customers, we have proposals, we have quotes, we have contracts and we have e-signatures. If I’m sending you a sales proposal for Insightly, I don’t want to send you something that’s generic across all four of those. I want it to be focused on your use case and what’s going to get you to sign with me. It’s about making sure you understand the value that my software as conveyed in my proposal is going to bring to you as a customer. So that’s really what I mean.. It’s got to be tailored. You obviously don’t want to spend, you know, a million hours crafting every single proposal from scratch. But because of the integrations like we have with Insightly, you can pull data in that helps you customize the proposal to be very specific to what you know that customer cares about. So that’s what I mean by customer focus. It’s about making sure that you understand the needs of the customer, that you’ve customized your proposal to their use case. And of course, if you do that, you’re going to see a higher close rate than something that’s more generic. It’s the same kind of thing. We always talk about our sales leaders with, you know, cold calls or cold outreach from SDRs.. The more customized, personalized and tailored it is, the higher it’s going to perform. For sure. Yeah, makes a ton of sense. So if you’re kind of restating to the customer that you heard them, you understand what they want, you understand what their goals are with, you know, adopting your software or whatever it is that you’re selling. And you show that in the proposal, Keith, right. That’s what you’re talking about, right? Exactly. Makes a ton of sense. And so, you know, one of the benefits of being able to send via a modern proposal system is the ability to see, hey, have they opened it right? Have they actually looked at this proposal? And so analytics is becoming more important. Talk to me about what you find to be helpful with analytics and what sales people need to think about. Yeah, it’s interesting. I thought that’s where you are going to go with talking about the PDF that you forward around because if you’ve got a PDF that’s a proposal that has been sent to you and you forward it to somebody else in your department, there’s no way that the person who sent you that PDF proposal has any idea what’s been done with it, Right? It came to you. Did you open it? Did you look at it?. Did you spend a lot of time on it? You sent it to somebody else.. Did they do that? Did they spend any time on it?. Was it forwarded to someone else in the chain and they might forward it back to somebody else in the department and you have no idea if it closes. So having analytics that are bundled deep into the software that generates the proposals is really important because they show that your prospect is engaging and spending time with your proposal. So at PandaDoc, we track things like the time spent on each individual page of the proposal, the links that are clicked, whether something was downloaded. We can see very clearly if our proposal was sent to another person at the company and we can see how many times that’s been opened. And that’s really a signal of interest that allows us to prioritize our next actions with our customer. So we can determine if they haven’t spent a lot of time, maybe we need to spend a little more time getting in front of that customer and making sure they open the proposal. We might send a reminder. If they haven’t looked at the pricing table, we can probably know that they’re not ready to sign regardless of how how much they’re telling us they are. And if they’ve sent it around, we know that there’s probably a bit more interest than if they just opened it by themselves. And so that’s really important. The other piece is the analytics allows you to sort of run testing within your proposals. So we talked about the format and getting the format right. Having analytics on different pages will allow you to know that certain pages are working because people are spending a lot of time there or digesting them, and you can swap out pages based on the analytics much in the way that you would run an AB test on a website. That’s the thing that I love about the analytics there, is it makes you look better, it makes you smarter as a salesperson, right? So you’re not sending the dreaded, hey, just following up to figure out what’s going on. You actually can see, are they engaging with what you’ve sent them? Are they engaging with it once or multiple times? Have they forwarded it? Is it truly something they’re considering? So it just, you know, whether they are or whether they aren’t, you have data now to kind of arm you with your follow up. Right. Right. I mean, and I see that the best sellers spend more time with the customers who have a better chance of closing based on what the analytics show us. And it really allows you to tailor that outreach as well, just as you said. So wow, I saw you spent a lot of time on the pricing table. Is that making sense? Can I help you with those versus just a generic outreach? That said, oh, I saw you got the proposal or you’re spending a lot of time on those customer stories that I put on page eight. Would it be helpful for me to connect you with one of those customers as a testimonial? You can really drive a much tighter engagement between your prospect and your seller. So we went through those four steps pretty quickly, but I’m just intrigued by something you said earlier on. You said 6 to 8 pages is kind of the ideal length and you encourage people to have at least one image in there. Is that somewhat based on AB testing that you’ve done, Keith? That’s based on the data that we’ve just seen across all the customers who have used PandaDoc. So we know that if there is an image embedded, it closes at a higher rate. I think it’s going to really depend on your use cases, which is why the mix of the analytics plus the formatting becomes really powerful. So if I can experiment with the formatting and then see that change I make in formatting, drive higher close rates and higher engagement rates from the analytics that I have, that becomes really powerful for me at making my proposals for my very specific business and my specific customers, much more successful at driving close rate. So one thing you know, often, especially with larger books of business or larger deals, enterprise deals, you might have a master services agreement or something like that. Do you try to incorporate that all into a Panda proposal or do you send that separately or what would you recommend? We usually append it at the end of a proposal, but we’ll have a clearly differentiated piece to the proposal, almost like a separator slide. You know, you get through the meat of the proposal and then it’s the MSA or the privacy agreement and it’s separated. So if you want to read it, you can or you send it to the lawyer and you can mark it. I think, you know, certain tools like PandaDoc allow you to really clearly point people to certain parts of the document to dive into. And so really, your lawyer doesn’t need to look at all the graphic imagery or the pricing table. They need to spend time on the master services agreement. And so you can call them out there versus you as the decision maker, probably want to spend more time upfront understanding whether this is the right vendor for you based on the information they’ve conveyed to you. Yeah. So you can kind of use the proposal as the the awesome looking UI for the rest of what you’re sending to the customer because MSA is frankly, who wants to deal with those unless you’re maybe a lawyer, maybe you like that. Keith, some great stuff here. I think a lot of sales reps probably get to the point that they’re sending the proposal and they’re like, they can already see the finish line. They’re like, wahoo, we’re almost there. I’m just going to shoot over the proposal and we’ll be done with it. But I mean, the fact of the matter is there’s so much more there. Yeah,. I mean, how many times as a sales leader do you see deals fall out of your late stage pipeline? And it’s more often than we want, right? I mean, this gives you the opportunity to have the extra steps to get it across the line in multiple ways. One, because you’ve set the bit early with a great looking proposal that stands out in the mind of the customer, and will make it through the stages at a higher rate. And at the late stage you can tell if a deal is starting to fall flat because the engagement with your proposal is starting to fall through and the analytics helps you point to that and resurrect it through reminders and diving in where you can make a difference. So that’s why we take a lot of pride in making sure we put our best foot forward in those proposals and using the analytics to drive the outcome so we get better close rates in the late stages of our pipeline. 100% agree and great final thoughts, Keith, Thank you. And thanks to everyone for joining us today on this episode of Closing Time. And we’ll see you next time.

You may also like:

See all episodes
Ghosting in Sales: How to Follow Up When Prospects Disappear
Sales Objection Handling: 8 Responses to the "I'm Not Interested" Objection
How Sales Leaders Can Foster an Environment Where Women in Sales Thrive