If you’re running or growing a B2B sales team, you’ve probably noticed: there’s no shortage of fancy software promising to “turbocharge” your pipeline. The problem? Most of it either doesn’t do what it says, doesn’t fit your team, or costs way more than it’s worth. This guide is for sales leaders, ops folks, or founders who want to scale their team without getting burned by shiny tools or buzzword soup.
Let’s get into how to actually evaluate go-to-market (GTM) software when you want real results—not just a bigger software bill.
Step 1: Figure Out What Problem You Actually Need to Solve
Before you even look at a demo, nail down what you need. Most teams skip this and end up with a Frankenstack that nobody uses. Start here:
- What’s slowing your team down? (Be honest. Is it manual data entry? Leads falling through the cracks? Reps not following up?)
- Where do you lose deals? (Is it discovery, proposal, closing, or post-sale handoff?)
- What’s your real bottleneck? (If you doubled leads tomorrow, would you explode or thrive?)
Write down the top 2-3 issues you want to fix or improve. Don’t let software vendors tell you what your problems are—they’ll always "solve" what they sell.
Pro Tip: If you can’t say, in one sentence, what you want the tool to do, you’re not ready to buy.
Step 2: Map Your Current Sales Process (Yes, Really)
You need a clear map of how things work today, not how you wish they did. Grab a whiteboard (or a napkin—whatever works) and jot down:
- Lead sources (Where do leads come from?)
- Handoffs (Who touches a prospect, and when?)
- Major steps (Demo, proposal, contract, onboarding, etc.)
- Current tools (Spreadsheet, CRM, call tool, etc.)
This isn’t busywork. You’ll be shocked at the gaps or weird workarounds you spot. Any tool you buy needs to fit your actual workflow, not some “ideal” one in a pitch deck.
Step 3: Decide What Kind of Tool You Need—And What You Don’t
Now you’re ready to look at categories. Most GTM software falls into a few buckets:
- CRM (Customer Relationship Management): Think Salesforce, HubSpot, Pipedrive.
- Sales Engagement Platforms: Outreach, Salesloft, or the newer SecondBody.
- Lead Sourcing & Data Tools: Apollo, ZoomInfo, Lusha.
- Revenue Intelligence / Analytics: Gong, Clari, InsightSquared.
- CPQ (Configure, Price, Quote): DealHub, PandaDoc.
What to ignore:
All-in-one tools that claim to do everything rarely do any one thing well. You’ll end up with a bloated system your team resents. Look for focused tools that play nicely with what you already use.
Step 4: Build a Shortlist—Don’t Let Vendors Do This For You
Once you know your needs and your process, start building a shortlist:
- Ask peers what they actually use (not just what’s “best in class”).
- Read real user reviews. G2 and TrustRadius are more useful than vendor case studies.
- Make sure any tool on your list integrates with your CRM—unless you want your team copy-pasting for the next year.
Narrow it down to 2-4 options. More than that and you’ll waste weeks in demo hell.
Step 5: Run a Hands-On Test (Not Just a Demo)
A slick demo is like a first date: everyone’s on their best behavior. Insist on a free trial or a pilot. Here’s how to do it right:
- Have your actual salespeople use it on real deals.
- Set a timer. How long does it take to set up an account, add a lead, send a sequence, etc.?
- Check for “gotchas”—does it break your other tools? Does it require hours of admin setup?
- See how it handles edge cases. (Can your SDRs and AEs both use it? Does it work with your weird custom fields?)
If you can’t get a pilot, that’s a red flag. Walk away.
Pro Tip: Watch out for tools that need “professional onboarding” just to get started. If it’s that confusing, your team will hate it.
Step 6: Ask the Hard Questions
Before you commit, grill the vendor. Here’s what to ask (and why):
- How do you handle data sync with our CRM? (If this breaks, nothing else matters.)
- What does user adoption really look like? (Ask for real stats, not just case studies.)
- How fast is support? (Try emailing their support team before you buy. See how they respond.)
- What’s the real all-in cost? (Are there implementation fees, seat minimums, required add-ons?)
- Can we export our data if we leave? (You don’t want to get stuck.)
Don’t be shy. If a vendor dodges these, it’s not a good sign.
Step 7: Crunch the Numbers—But Don’t Just Look at Sticker Price
The cheapest tool isn’t always the cheapest in the long run. Here’s what actually matters:
- Time to value: How soon will you see results?
- Training and ramp-up: Will your team need days of training, or can they figure it out in an afternoon?
- Maintenance: Does it break often? Will you need a dedicated admin?
- Hidden costs: Usage limits, required integrations, or surprise price hikes.
Pro Tip: Ask the vendor for a plain-English quote, not just a spreadsheet of line items. If you can’t explain the pricing to your CFO in 30 seconds, it’s too complicated.
Step 8: Get Buy-In From the People Who’ll Actually Use It
The #1 reason sales tools fail? The team just doesn’t use them. Get a few frontline reps or managers in on the pilot and listen to their feedback—really listen.
- Will it make their day easier, not harder?
- Does it automate the boring stuff, or just add more steps?
- Is it “nice to have” or “can’t live without”?
If your team rolls their eyes, keep looking. The right tool should get at least a few people genuinely excited.
Step 9: Keep It Simple—And Be Ready to Change Your Mind
Don’t overthink it. No tool will fix a broken process or magically make your team care. Pick the simplest option that solves your biggest problem. Make sure you can get out if it’s not working.
- Start with a pilot or monthly plan if you can.
- Don’t sign multi-year agreements unless you’re truly sure.
- Regularly check: Is this still solving the problem we bought it for?
What Actually Matters (And What Doesn’t)
Matters: - Fit with your actual workflow - Easy adoption - Real, provable ROI - Reliable support
Doesn’t matter: - Fancy AI features you’ll never use - Cool dashboards nobody looks at - “Synergy” with 10 other tools you don’t own
Ignore the noise. Most teams need a tool that does a few things really well, not one that promises to do everything.
Final Thoughts
There’s no perfect B2B GTM tool, just the right one for your needs (today). Cut through the hype, focus on your real problems, and keep your stack as simple as possible. When in doubt, pilot first, commit later. Iterate as you grow—what works now might not in a year, and that’s okay. The best sales teams aren’t the ones with the most software. They’re the ones who actually use what they have.
Now, go fix the real problems. The right tool should help—not get in your way.