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  • Mercer Smith-Looper • Feb 9, 2021

9 things to look for when picking proposal software

Looking for a proposal software can be like looking for the other glass slipper. Here are nine things to consider during your search.

If you were looking to purchase something to shelter you in a storm, you probably wouldn’t just buy a raincoat. Sure, it could do some of the job, but in the event of an actual storm, you’d need something to protect you in a much bigger way- ideally something that’s been designed for weathering storms. The same should be said when thinking about purchasing proposal software.

Tons of companies rely on time-consuming and tiring processes when it comes to writing up proposals. Sure, you can use a PDF or Google Docs, but you spend time manually doing tons of formatting and editing when you could just use a system to do it for you. 

In sales, speed matters. According to The Brevet Group, 30-50% of sales go to the vendor that responds first. So, those thirty minutes you spend making sure all of your bullet points match could cost you a deal.

Picking a proposal software that meets all of your needs will save you time and energy on things you probably don’t even think about twice. They’ll make the best performing, best-looking proposals for significantly less effort than your old proposals used to. As you go into the vetting process, think about these two questions:

  • What is your team’s most significant pain around the proposal process? 
  • What do you want to achieve by using or changing to a new proposal software?

Beyond those two personal responses, here are nine things to look for when picking a proposal software.

Design functionality

Most of us aren’t designers. A proposal software with excellent design functionality will cut down on creation time and produce consistent, branded proposals that impress your prospects. Look for tools that allow you to:

Having these elements right at your fingertips without needing to add any extra functionality will make your sales team’s lives so much better.


Having more information about your customers helps you craft the best possible experience and reach out to them proactively if they need help. Beyond that: it can be super helpful to have a view of which stages all your active proposals are in. 

With insight into every time someone opened the document, who they sent it to, how much time people spend with each component, and what actions they’ve taken within the doc, you could generate the perfect follow-up cadence explicitly triggered by user behavior, rather than elaborate guesswork. Find a proposal software that will give you more information, rather than less.

Version control

I use the “undo” version in text editors all the time. It’s useful to have the functionality to revert to a previous version of my document or trace back my steps to follow my thought processes. When working collaboratively, it’s even more critical. Version controls in proposals help you have an audit trail of who changed what and allows you to revert to previous pricing or phrasing that you’ve used in the past.

Web-based formatting

No one likes PDFs. Whatever proposal software you end up going for should make it easy to send your prospects a direct link to your proposal. You don’t want anything interfering with the smoothness of your sales process. Don’t make your prospects download any new software or programs to view the things you send them. Send a link that brings them directly to the page they need to land on to make conversion even more effortless.


According to a recent study, companies spend an average of $325 per month per sales rep on tooling across an average of 5.8 tools. With that many tools, asking your team to do manual data entry is a sure-fire way to end up with incorrect or outdated information. Make sure your proposal software has integrations with the critical software that your team works to keep everything in sync and organized.

Some of the things that it should integrate with are: 

  • Payment and invoicing systems
  • Contract management systems
  • CRM
  • File storage systems, like Google or Dropbox
  • Project management systems

Imagine if your proposal software could automatically fill customer information into a template, or your customers could purchase right within your proposal? With these integrations, they could.


An excellent proposal software will take your sales process and allow you to turbocharge it with automation. Look for things like the ability to offer click-to-call functionality, automatic document generation, event triggering and remarketing ads, and even reminders through SMS or email for individuals that opt-in. Take the work out of your reps’ hands, and let the software handle the small stuff for you.


Working together might sound like a given, but so many of the tools companies use to create proposals do not have excellent collaboration functionality. Look for a tool that allows your reps to work together in real-time, no matter where in the world they are. They should have complete visibility to who is changing what at precisely the moment that they do it.

Find a tool that allows you granular control over user permissions and actions, such as what each person can edit or share, who can post comments, and if certain parts of proposals should be off-limits. These types of features will make your team’s ability to work together even stronger.


You don’t need to reinvent the wheel every time. Make use of templating and a content library to allow you to pick and choose what you need quickly each time you draft a new proposal.

You’ll be writing similar content each time you create a proposal—why not make it easy on yourself? Maintain consistency across all of your essential documents and take the guesswork out of your team’s generation process. The ability to pull a specific template and modify it easily with pieces from a standing library of content is valuable. It will give your sales reps back the time they need to sell even better.


There’s tons of confidential information in your proposals for both you and your customers. All of the pricing and payment information, their names, and other sensitive data are things you should want to protect. The importance of safeguarding this information, both for you and them, can not be overstated.

Beyond that, you can ensure that your e-signing and payment functionalities are also safe with additional security levels. No one wants to lose their customers’ trust or end up blasted on Twitter for a preventable data breach.

Find what fits

Even though all of these things seem important to us, they might not be necessary for you. Start by taking a holistic view of what you want to change about your current proposal process and what is important to you. From there, make sure that the proposal software you’re going with aligns those things.

Maybe, for instance, automation isn’t that important to you, but version control and design are. Develop a list of high-level requirements by picking and choosing what you need to fulfill your business strategy. Your perfect proposal software is right around the corner.

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