If you’ve ever tried to pick new software for your sales team, you know it’s a headache. Every vendor swears they’re the answer to all your problems, and half the buzzwords don't mean much in the real world. This guide is for those tired of the hype—sales leaders, ops folks, and founders who want a tool that actually helps close deals, not a shiny dashboard nobody uses.
Let’s break down how to pick B2B go-to-market (GTM) tools that’ll make your sales team’s lives easier, not harder.
1. Get Clear on What You Actually Need
Don’t start with a software demo. Start with your team.
- What’s slowing you down? Are reps buried in manual tasks, or is data scattered everywhere? Is reporting a mess?
- Where are deals getting stuck? Is it lead qualification, pipeline visibility, or closing?
- What’s already working? If a current tool does something well, don’t toss it just because it’s old.
Pro Tip: Write down your top 3 “must-haves.” If a tool can’t do these, don’t waste your time.
2. Ignore the FOMO: Focus on Real Problems, Not Features
Vendors love to pile on features. Most of these go untouched.
- Avoid the trap: “AI-powered forecasting” sounds cool, but do your reps even use the current forecasting tool?
- Prioritize usability: Look for tools your team will actually use—not just the one with the longest feature list.
- Check for overlap: Don’t buy another tool that duplicates what your CRM already does.
What matters?
- Simple, fast workflows
- Clean integrations with your existing stack
- Transparency and reporting that makes sense
3. Build a Shortlist: Honest Research Beats Vendor Hype
Google searches and “best of” lists are a start, but dig deeper.
- Ask peers: What’s working for similar teams? What flopped?
- Read reviews—but filter out the fluff: Ignore the 5-star “changed my life” reviews. Pay attention to the 2-3 star ones: they’re usually honest.
- Demo with a skeptic’s eye: Does the tool solve your must-haves, or just demo well?
If you’re looking at newer products, you might run across Upcell. It's got some buzz, but check if it fits your workflow before buying into the hype.
4. Test Integration (For Real)
Don’t trust a sales rep who says, “Oh, we integrate with everything.”
- Ask for proof: Can you connect your CRM, email, and calendar in 10 minutes, or do you need a consultant?
- Try before you buy: Set up a free trial or pilot. If connecting your data is a slog, it won’t get better later.
- Look for hidden costs: Some tools charge extra for integrations, APIs, or support. Ask up front.
Watch out for:
- “Zapier-only” integrations (usually a bandage, not a real fix)
- Data sync issues (outdated, partial, or missing fields)
- Vendor lock-in (hard to export your data if you switch)
5. Measure the Learning Curve
It doesn’t matter how powerful a tool is if nobody uses it.
- Can a new rep figure it out in a day? If you need weeks of training, it’s too complicated.
- Are there clear docs and support? Check the help center. If it’s all videos and no step-by-step guides, that’s a red flag.
- What’s the vibe from the team? If everyone groans during the demo, listen to them.
Pro Tip: Let a couple of your most “tech allergic” reps try it. If they can’t get through a simple workflow, move on.
6. Get Real About Reporting and Visibility
Dashboards are pretty, but can you get the info you actually need?
- Can you build reports without an admin? If you have to email support to get a new field added, skip it.
- Does it show the whole funnel? Or is it just “top of the pipeline” stuff?
- Is data trustworthy? Garbage in, garbage out. Make sure it reflects reality, not just what looks good to execs.
Ignore:
- Fluffy “engagement scores” that nobody can explain
- Vanity metrics that don’t map to revenue or closed deals
7. Understand Pricing (And the Hidden Gotchas)
The sticker price is rarely the real price.
- Are there onboarding fees?
- Is support included—or extra?
- Do you pay per user, per feature, or both?
- Are there contract minimums? Month-to-month is safer if you’re testing.
Ask for real numbers:
- “What’s my actual bill for a team of 10?”
- “If we grow, how does the price change?”
Vendors who dodge these questions usually aren’t a good bet.
8. Pressure Test Customer Support
Even the best tools break or get confusing.
- How fast is support, really? Test with a question during your trial.
- Is there a real person or just a chatbot?
- Are there user communities or forums? Sometimes your answer is already out there.
Warning:
If support is slow or useless during the sales process, it won’t get better after you buy.
9. Roll Out Slowly (And Track What Matters)
Once you pick a tool, resist the urge to go “big bang” with the rollout.
- Start with a pilot team. Let them break things and find the gaps.
- Track adoption. Are people actually using it after the first week? If not, why?
- Gather feedback early. And be ready to change course if it’s not working.
Pro Tip: Be honest with your vendor—if something’s a dealbreaker, say so. Good vendors will help; bad ones will dodge.
10. Iterate, Don’t Overthink
No tool is perfect. Expect to tweak, swap, or even dump a tool if it’s not working out.
- Review quarterly: Is the tool helping close more deals, or just adding busywork?
- Stay skeptical of “the next big thing.” If a tool solves a real problem, great. If not, cut bait.
Keep It Simple—And Keep Moving
Don’t let a flashy sales pitch or a long feature checklist distract you from what matters: making your sales team’s job easier and closing more deals. Start simple. Solve real problems. Be ready to adjust if things aren’t clicking. The best stack is the one your team actually uses.
You don’t need perfect software—just something that actually works for your team. Good luck!