If you're in charge of picking proposal software for your sales team, you already know the pain: endless demos, “feature matrices,” and every vendor promising to make your life easier. But most guides gloss over what really matters when you’re choosing between Proposify and the rest of the B2B proposal software out there.
This guide isn’t here to sell you a dream. It’s here to help you cut through the noise and actually compare what matters—so you can pick the tool that fits your team, your deals, and your sanity.
Step 1: Get Real About Your Team’s Workflow
Before you look at a single feature list, map out how your sales team actually works today. Don’t just ask your sales director—talk to the reps who send proposals, the manager who tracks them, and the folks chasing signatures.
Ask yourself:
- Who creates proposals? Is it reps, sales ops, or marketing?
- How complex are your proposals? A few pages and a price, or multi-section, legally-reviewed beasts?
- What tools do you use now? Google Docs, PDFs, email, or something “custom” that’s mostly spreadsheets?
Write down the headaches: “We lose track of who’s signed,” “We can’t see who’s viewed the doc,” “Formatting is a nightmare.” Don’t skip this step. If you don’t know your pain points, you’ll get distracted by features you’ll never use.
Pro Tip: If everyone hates your current process, figure out why before you start shopping. Software alone rarely fixes broken habits.
Step 2: Identify the Must-Haves (and Ignore the Fluff)
Every proposal platform has a laundry list of features. Here’s what’s usually worth caring about—and what’s just marketing.
What Actually Matters
- Template Management: Can you lock down branding and pricing? Is it easy to update?
- E-Signatures: Legally binding, easy to use, and works on mobile.
- Analytics & Tracking: See who’s opened, viewed, forwarded, and signed.
- CRM Integration: Works with Salesforce, HubSpot, or whatever you actually use.
- Collaboration: Can multiple people (sales, legal, product) edit or comment?
- Content Library: Reusable sections, case studies, T&Cs, etc.
- Permissions & Approvals: Restrict who can send what, and require approvals when needed.
What Usually Doesn’t Matter (Unless You’re Huge)
- AI-Powered Anything: Most “AI” features are just glorified autofill or basic content suggestions.
- Hyper-Custom Animations: Nobody ever bought because your proposal had a spinning logo.
- Dozens of Integrations: If you’re only using two tools, don’t pay extra for fifty integrations.
- Obscure Metrics: Heatmaps and “engagement scores” sound cool, but are rarely actionable.
Pro Tip: Force yourself to pick the top three features you actually need. Everything else is a bonus.
Step 3: Shortlist the Real Contenders
Now that you know your must-haves, build a short list. For most B2B teams, the serious options usually include:
- Proposify
- PandaDoc
- Qwilr
- DocuSign (for some basic needs)
- Better Proposals
Don’t get stuck in analysis paralysis. Most sales teams don’t need a unicorn—just something that works. Check review sites (like G2 or Capterra), but be skeptical of five-star reviews written in “enterprise-speak.”
Step 4: Compare Side by Side (Not Just on Features)
Here’s how to actually line them up:
1. Ease of Use
- Can your least tech-savvy rep send a proposal without cursing?
- Is the editor drag-and-drop, or do you need HTML skills?
- How fast can you duplicate and tweak a proposal?
2. Setup and Onboarding
- How long to import your templates and branding?
- Is there decent documentation or live support?
- What’s the learning curve for a new hire?
3. Workflow Fit
- Does it fit how your team works—or does it force you to change?
- Can you automate approvals, or does everything go through one admin?
- How are proposals tracked and followed up?
4. Integration Reality
- Does it actually sync with your CRM (not just “connect”)?
- Are updates instant, or does it lag?
- Can you push data both ways, or only export PDFs?
5. Pricing Transparency
- Is pricing public, or do you have to “talk to sales”?
- Are there hidden fees for users, signatures, storage, etc.?
- Can you scale up or down easily, or are you locked in?
Pro Tip: Sign up for a free trial with two reps and see who complains less after a week.
Step 5: Go Beyond the Demo—Test With Real Deals
Most sales teams get wowed by a slick demo, but that’s not real life. Here’s how to pressure-test your shortlist:
- Run a Real Proposal Through Each Tool: Use an actual deal (redact the details if you want). Time how long it takes from draft to sent.
- Ask for Stakeholder Feedback: Get input from sales, legal, and whoever else touches proposals. Did anyone hit a blocker?
- Check Customer Experience: Send a test proposal to yourself and a friend. Is it easy to view, sign, and save? Does it look professional on mobile?
- Track Support Response: Hit up customer support with a real question. How fast and how useful are they?
Red Flags: - You need a “power user” to make it work. - The proposal looks weird in Outlook or on a phone. - Support takes days to respond—or just sends you to a help article.
Step 6: Look at the Long-Term Fit
Switching proposal software isn’t fun. Make sure you’re not just picking for now, but for next year:
- Can it grow with your team? Easy to add users, templates, and permissions.
- Is the company stable? Check funding, reviews, and update history.
- How often do they ship real improvements? Not just UI tweaks or buzzword features.
If you’re stuck between two options, go with the one that’s simpler to use. Fancy features almost never outweigh daily usability.
What About Proposify?
Let’s be honest: Proposify is popular for a reason. It nails the basics—template management, e-signatures, and tracking—without being overly complicated. Most midsized B2B sales teams find its editor and analytics straightforward. Integrations with major CRMs are solid (but, as always, test with your own data).
Where Proposify can fall short: if you need hyper-advanced workflow automation or want a “wow” factor with interactive proposals, some competitors (like Qwilr) might edge it out. And if your needs are dead simple, you might find Proposify’s learning curve steeper than a barebones tool.
Bottom line: it’s a strong choice if you want a balance of control and ease of use, but don’t expect it to magically fix a broken sales process.
Step 7: Don’t Overthink It—Pick, Launch, and Iterate
Once you’ve tested your top pick with a real deal, stop comparing and just go for it. The perfect proposal tool doesn’t exist, and every platform will force a little compromise.
- Roll it out to a small team first.
- Collect feedback—what’s actually working, what’s driving people nuts.
- Tweak templates and workflows as you go.
Most importantly, don’t let software decisions drag on for months. The sooner your reps stop wrestling with Word docs and start sending clean, trackable proposals, the sooner you see results.
Want to compare proposal tools like a pro? Start with your real workflow, ignore the shiny stuff, and pick what feels easiest to live with. That’s what your future self—and your sales team—will thank you for.