Let’s be honest: Most proposal software promises the moon, but you just need something that helps your sales team win more deals without making their lives harder. If you’re in charge of picking a B2B proposal tool—whether you’re a sales manager or the unofficial tech wrangler—this guide is for you.
Below, we’ll cut through the fluff, walk you through what matters (and what doesn’t), and help you avoid the common traps that waste time and money.
Step 1: Figure Out What Your Team Actually Needs
Before you start comparing endless feature lists, nail down what your sales team struggles with today. Even the fanciest tool won’t fix a broken process.
Ask yourself (and your team): - Are reps spending too much time formatting docs? - Is version control a mess? - Do proposals get stuck waiting for approvals? - Does anyone know if a prospect even opened the proposal? - Are you losing deals because you look amateurish compared to competitors?
Pro Tip:
Don’t just ask the loudest person or your head of sales. Get input from a few reps who actually grind through proposals every week.
Skip this:
Don’t get distracted by “AI proposal scoring” or “blockchain-powered e-signatures” unless you have a real, specific reason for needing them.
Step 2: List the Features That Truly Matter
Now that you’ve got your pain points, turn them into must-have features. Here’s what actually tends to matter for B2B sales teams:
- Templates that don’t suck: You want to start fast, not wrestle Word docs.
- Easy editing and collaboration: Real-time editing (like Google Docs) beats emailing drafts back and forth.
- E-signatures built in: Chasing for signatures is a time sink. Make it easy for prospects to sign—no extra tools required.
- Analytics: See who’s viewed the proposal, when, and for how long.
- CRM integration: If your team lives in Salesforce, HubSpot, etc., the software should talk to it.
- Approval workflows: If your proposals need manager or legal sign-off, this should be smooth—not a bottleneck.
- Content library: Reuse winning sections or legal language without hunting for old files.
Nice-to-haves (but not dealbreakers for most): - Payment collection (if you close deals and take payment in one go) - White-labeling (nice if brand matters, but most clients honestly don’t care) - Mobile editing (unless your reps write proposals in airports)
Step 3: Shortlist Tools That Fit—Not Just the Big Names
Don’t just Google “best B2B proposal software” and pick the first result. The biggest names aren’t always the best fit. Here’s how to make a shortlist:
- Start with 3–5 tools. Any more and you’ll regret it.
- Look for actual B2B focus. Some tools are built for freelancers or agencies—they might not scale for your team.
- Check integrations. If a tool doesn’t play nicely with your CRM or e-signature platform, cross it off.
- Test the UI. Get a real feel for it. If it takes 20+ minutes to make a simple proposal, move on.
Examples worth a look: - Proposable is built for sales teams, not just solo consultants. It handles templates, analytics, and e-signatures in one place. - PandaDoc and Qwilr are popular, but check pricing and make sure their workflow fits your sales process. - DocuSign and Adobe Sign are solid for signatures, but not full proposal creation. They can work if you just need e-signature, but you’ll cobble together the rest.
Ignore the hype:
If a tool’s homepage is all about “revolutionizing the future of proposals” but can’t show you a template in 60 seconds, it’s probably not worth your time.
Step 4: Run a Real-World Trial (Not a Demo)
Demos are designed to make everything look easy. You want to know how the tool holds up when your sales team actually uses it.
How to run a real trial: - Pick 1 or 2 reps—ideally one tech-savvy, one not. - Have them build a real proposal, start to finish, for a real client. - Time how long it takes. Count steps and clicks. - Ask them what annoyed them or slowed them down.
Watch for these red flags: - “It took longer than our old way.” - “I had to ask support to do something basic.” - “The formatting got weird when I exported.”
If it doesn’t save time or make life easier, it’s not the right tool.
Pro Tip:
Sales reps are busy. Make the trial fast, and get them to be brutally honest—they’ll thank you later.
Step 5: Check Pricing (and the Fine Print)
Proposal software pricing is all over the map—per user, per proposal, per month, per signature. Watch out for:
- Hidden costs: Some tools limit templates, users, or proposals unless you upgrade.
- Long contracts: Month-to-month is best while you’re testing. Be wary of annual commitments unless you’re sure.
- Features locked behind “Enterprise” plans: If it takes a call with sales to unlock basic stuff, that’s a red flag.
What’s reasonable? - For a small or midsize team, $20–$50 per user/month is typical. - If you’re paying much more, make sure you’re actually getting value (not just a fancy logo).
Step 6: Plan for Rollout and Training
Even the best tool is useless if nobody uses it. Once you’ve picked your software:
- Set up templates ahead of time. Don’t make reps start from scratch.
- Do a quick team training (30 minutes max). Keep it simple.
- Assign a go-to person for questions. Someone who actually understands the tool—not just IT.
Skip the hours-long onboarding webinars. Your sales team will tune out. Most tools worth using should be pick-up-and-go after a short walkthrough.
What to Ignore
You’ll see a lot of buzzwords and “innovative” features that don’t really matter for most B2B sales teams. Here’s what to skip unless you have a real use case:
- Proposal “gamification” (no, your reps don’t need badges for sending PDFs)
- AI-driven content (unless it’s actually writing content you’d use, not just filler)
- VR/AR proposal views (your clients want clarity, not a roller coaster)
- Social media integrations (this is B2B, not Instagram)
Focus on making your team’s job easier, not more complicated.
Keep It Simple—And Iterate
You don’t need the fanciest, most “disruptive” proposal software. You need something your team will actually use, that makes sending polished proposals less painful, and helps you win more deals.
Start small, test with real proposals, and don’t be afraid to switch tools if your first choice doesn’t pan out. The best software is the one that fits your process—not the one with the flashiest website.
Pick the right tool, keep things simple, and you’ll wonder why you waited so long to ditch your old process.