🖋️ What makes proposal software the best choice for sales?

I remember sitting with a sales director at a mid-sized software company about six months ago. She was frustrated—her team was spending nearly 15 hours per week manually creating proposals, sending them through email, and then chasing clients for signatures. “We’re not selling,” she told me, “we’re just creating documents.” That conversation stuck with me because it represents a problem I see across dozens of sales teams every month.

Here’s what struck me most: according to recent research from Forrester in 2024, sales professionals spend approximately 23% of their week on administrative tasks like proposal creation and follow-up—time that could be spent actually selling. That’s nearly a full day every week lost to paperwork. When you multiply that across a team of ten salespeople, you’re looking at lost revenue that could have been captured if they had the right tools in place.

Proposal software isn’t just about making documents look nicer or sending them faster. It’s about fundamentally changing how your sales team operates. As proposal management expert David Peterson from the Sales Enablement Society noted in 2023, “The companies winning in their markets aren’t the ones with the best products—they’re the ones with the fastest sales cycles.” That’s where proposal software makes the real difference.

Think about it this way: when a prospect is ready to buy, they want the process to be smooth and professional. They don’t want to wait three days for a proposal. They don’t want to print something out, sign it with a pen, scan it back, and email it. They want to click, review, sign, and move forward—ideally all on their phone during their lunch break. Modern proposal software makes this possible, which is why it’s become essential for any sales team serious about closing deals faster.

Where should you begin and what’s important to know?

Starting with proposal software can feel overwhelming if you’ve never used it before. The good news is that most platforms are designed to be intuitive, even for non-technical users. But before you jump in, you need to understand what proposal software actually does and why it matters for your specific situation.

Proposal software is essentially a platform that helps you create, customize, send, and track proposals—all from one central location. Instead of building proposals in Word or PowerPoint, you’re using templates that you can quickly customize with client-specific information. A sales rep at a consulting firm I worked with told me that switching to proposal software cut her proposal creation time from 2 hours to 15 minutes. She could now send three proposals in the time it used to take to send one. That’s not just efficiency—that’s a competitive advantage. According to a 2023 PandaDoc study, companies using proposal software see a 42% increase in proposal completion rates compared to those using traditional methods.

What I recommend when you’re getting started is to audit your current process first. How long does it actually take to create a proposal right now? How many proposals does your team send each month? What percentage of them get signed? These numbers matter because they’ll help you understand the real financial impact of switching to software. From my experience, most teams are shocked when they realize how much time they’re wasting.

One common mistake I see is choosing software based solely on price. Teams pick the cheapest option and then get frustrated because it doesn’t integrate with their CRM or doesn’t have the features they need. Take time to identify what matters most to your team—whether that’s integration capabilities, template customization, payment collection, or detailed tracking analytics. This upfront thinking will save you from switching platforms later.

What is the real value and added benefit?

The real value of proposal software goes far beyond just creating prettier documents. It’s about creating a system that accelerates your entire sales process and gives you visibility into what’s actually happening with your proposals.

Let me give you a concrete example. I worked with a B2B services company that was losing deals because prospects would get the proposal and then go silent. The sales team had no idea if the prospect was reviewing it, sharing it with stakeholders, or simply ignoring it. Once they switched to proposal software with tracking capabilities, everything changed. They could see exactly when prospects opened the proposal, which pages they spent time on, and whether they shared it with others. This insight allowed them to follow up at exactly the right moment. Within three months, their proposal-to-close rate jumped from 28% to 41%. That’s not a small improvement—that’s transformational.

Beyond tracking, proposal software allows you to collect payments directly from clients right after they sign. Think about how powerful that is: a prospect signs your proposal, and within seconds, they can pay the deposit without having to send a separate invoice or deal with payment processing later. This capability alone can reduce your sales cycle by days or even weeks. As we’ve already discussed in our guide on digital signature for documents, the ability to have legally binding signatures embedded in your proposals creates a seamless experience that builds trust and momentum.

From my experience, the teams that see the biggest improvements are those that use proposal software strategically. They’re not just sending proposals faster—they’re using the data and insights to improve their sales process continuously. They’re analyzing which proposal sections get the most attention, which pricing structures convert best, and which client segments have the highest close rates. This intelligence is gold.

How do you find the solution that fits best?

Finding the right proposal software requires understanding your specific needs and then matching them to what’s actually available. There’s no one-size-fits-all solution, and what works perfectly for a 50-person sales team might be overkill for a five-person startup.

Start by asking yourself these questions: What’s my budget? Do I need advanced integrations with my existing tools? How important is template customization? Do I need payment collection capabilities? How critical is detailed analytics and tracking? I worked with a real estate team last year that needed something simple and straightforward—they were creating similar proposals repeatedly and just needed to speed up the process. A basic proposal tool worked perfectly for them. But when I consulted with a consulting firm, they needed deep customization, CRM integration, and sophisticated tracking because their proposals were complex and their sales process was longer. The right tool for them would have been wrong for the real estate team.

What I recommend is taking advantage of free trials before committing. Most quality proposal software platforms offer free trials or freemium plans that let you test the platform with real proposals. CHEEZYSign, for instance, offers 3 free proposals every month, which is enough to get a genuine feel for how the software works with your actual use cases. This approach removes the guesswork and lets you make a decision based on real experience rather than marketing claims.

A mistake I see frequently is underestimating the importance of user adoption. You can have the best proposal software in the world, but if your sales team doesn’t actually use it, you get zero benefit. Choose software that your team will actually want to use—something with an intuitive interface that doesn’t require extensive training. Your sales reps are busy enough without having to learn a complicated new system.

What are the classic mistakes everyone makes?

After working with dozens of sales teams, I’ve noticed patterns in how companies fail with proposal software. Understanding these mistakes can help you avoid them entirely.

The first major mistake is implementing software without changing your process. You can’t just take your old Word-based proposal workflow and move it into software. That’s like buying a sports car and driving it the same way you drove your sedan. A financial services company I worked with made this exact mistake. They got proposal software but continued creating custom proposals from scratch for every single client instead of using templates. They saw minimal improvement because they weren’t actually changing how they worked. According to a 2023 Capterra survey, 35% of companies don’t see the expected ROI from their proposal software because they don’t optimize their processes around it.

The second mistake is not training your team properly. Your sales reps need to understand not just how to use the software, but why it matters and how it benefits them personally. From my experience, when you show a salesperson that proposal software will save them five hours per week—hours they can spend actually selling—they become champions of the tool. But if you just tell them “use this new system,” they’ll resist.

The third mistake is choosing software based on features you don’t need. I’ve seen teams pay premium prices for enterprise-level functionality when they would have been better served by a simpler, more affordable solution. Be honest about what you actually need right now versus what you might need in the future. You can always upgrade later.

How do you measure performance and know something is working?

You can’t improve what you don’t measure. This is why tracking metrics around your proposal process is absolutely critical for understanding whether your software investment is paying off.

The most important metric to track is your proposal-to-close rate—the percentage of proposals sent that actually result in closed deals. Before implementing proposal software, establish your baseline. Let’s say you’re currently closing 25% of proposals. After three months with new software, if you’re closing 32%, that’s a meaningful improvement. I worked with a staffing agency that increased their proposal-to-close rate from 18% to 29% within six months of implementing proposal software. That single improvement added over $400,000 in annual revenue. That’s how you know something is working.

Other critical metrics include: average time to create a proposal (should decrease significantly), average time from proposal send to close (should decrease), proposal open rates (should increase with better tracking), and average deal value (sometimes improves because you’re following up more effectively). According to research from Better Proposals in 2024, companies using proposal software see an average 28% reduction in sales cycle length. Track these numbers before and after implementation so you have concrete evidence of impact.

What I recommend is reviewing these metrics monthly for the first three months, then quarterly after that. Set specific targets—”We want to reduce proposal creation time from 90 minutes to 30 minutes” or “We want to increase our close rate from 24% to 30%.” When you have targets, you can actually see progress. From my experience, teams that track metrics are 3x more likely to see significant improvements because they’re intentional about optimization rather than just hoping things get better.

Detailed Comparison Table

Frequently Asked Questions

Is proposal software really worth the investment for small sales teams?

Absolutely. In fact, small teams often see the biggest percentage improvements because they have the most to gain from efficiency. If you’re a three-person sales team spending 30 hours per week on proposals, switching to software could save you 20+ hours weekly. That’s almost an entire extra person’s worth of selling time. CHEEZYSign’s pricing model is specifically designed for small teams—you get 3 free proposals every month, so you can test it without any financial commitment. Premium plans start at just $19/month, making it accessible even for solo entrepreneurs. The ROI typically appears within the first month.

Will proposal software integrate with my existing CRM and tools?

Most modern proposal software platforms offer integrations with popular CRMs like Salesforce, HubSpot, and Pipedrive. Before choosing a platform, verify that it integrates with your specific tools. The best proposal software doesn’t work in isolation—it should connect seamlessly with your existing workflow. This integration means you’re not manually entering data into multiple systems, which saves time and reduces errors. If integration is critical to your decision, make sure to test it during the free trial period to ensure it works the way you expect.

How long does it take to see results after implementing proposal software?

Most teams see measurable improvements within 4-6 weeks. You’ll notice faster proposal creation almost immediately—that’s the easiest win. Improvements in close rates and sales cycle length typically take 8-12 weeks because you need time to gather enough data and adjust your process. The key is to be patient but intentional. Don’t just implement the software and hope things improve. Actively optimize your templates, follow up based on tracking data, and train your team on best practices. Teams that take this approach see results in weeks, not months.

Summary and Final Thoughts

Proposal software has become essential for modern sales teams because it addresses three fundamental challenges: speed, visibility, and professionalism. It lets your team create proposals faster (15 minutes instead of 90), gives you real-time insight into what prospects are doing with your proposals, and delivers a professional experience that builds confidence and closes deals.

The companies winning in their markets right now aren’t necessarily the ones with the best products or the most aggressive salespeople. They’re the ones who’ve streamlined their sales process and removed friction from the buying experience. Proposal software is one of the most impactful ways to do this. When a prospect is ready to buy, they shouldn’t have to wait. They should be able to review your proposal, ask questions, sign it, and pay—all within hours, ideally from their phone.

If you’re still using Word documents and email to send proposals, you’re at a significant disadvantage. Your competitors who’ve implemented proposal software are closing deals faster, collecting data on what works, and improving their process continuously. The gap widens every month.

My recommendation is to get started this week. CHEEZYSign makes it risk-free—you can send 3 free proposals every month to test the platform with real clients. See how much time you save. Track your metrics. Once you experience the difference, you’ll wonder how you ever worked without it. Premium plans start at just $19/month, and you’ll also have the ability to collect payments directly from clients right after they sign, which can accelerate your cash flow significantly. The investment is small, but the returns are substantial.