If you’re in charge of picking software for your sales team, you already know: there’s no shortage of tools that promise to “revolutionize your pipeline.” But most aren’t built with your sales reps in mind, and a lot of them add more work than they save. This guide is for folks who want to cut the hype and pick something that actually helps the team close deals—not just look good on a slide deck.
Step 1: Get Clear on What Actually Matters
Before you even start looking at demos or reading G2 reviews, hit pause. What’s the real problem you’re trying to solve? Be honest—most teams don’t need yet another dashboard or a fancy AI-powered anything. Start with these questions:
- Where exactly are reps losing time or deals? (Is it prospecting, follow-up, data entry?)
- What does your team complain about in your current system?
- What’s the minimum you need to fix, so sales can focus on selling?
Pro Tip:
Talk to the people who’ll use the tool every day. Ask them what actually slows them down. Executives love analytics, but your sales team might just want a faster way to send emails.
Step 2: Make a Short List of Tools That Fit Your Use Case
Don’t let Google’s search results or LinkedIn ads set your agenda. Once you know what you need, look for tools that solve that specific problem. Ignore the all-in-one platforms if you only need one feature. Some good places to look:
- Ask peers at similar companies what they use—and what they ditched.
- Visit trusted review sites, but read the bad reviews too.
- Look for tools that are clear about what they don’t do.
If you’re looking for email deliverability or inbox warmup, for example, check out Warmuphero as a focused option. It’s not trying to be everything, just solves a real need.
Step 3: Dig Into the Features—But Don’t Get Distracted
Vendors love to pile on features. Here’s what to focus on:
Must-Haves
- Ease of use: Can your team pick it up without hours of training?
- Core functionality: Does it do the one or two things you actually need, reliably?
- Integrations: Does it work with your CRM and email, or does it live in its own universe?
- Security & compliance: Especially if you’re handling sensitive data.
Ignore (for now)
- Fancy dashboards you’ll never use
- AI “insights” that just regurgitate your CRM
- Gamification (unless your team actually loves it—not just the vendor’s sales rep)
Pro Tip:
Make a “must-have” vs. “nice-to-have” list before talking to vendors. If a feature isn’t on your must-have list, don’t let a sales demo change your mind.
Step 4: Put the Tools to the Test—Don’t Trust the Demo
Never buy based on a demo alone. Demos are designed to make everything look easy. What you really want is a free trial or a pilot, with real data and real users.
- Set up the tool yourself, or have a rep do it with you watching.
- Try importing real leads or connecting your actual CRM/email.
- Ask sales reps to use it for their real work, not just test data.
Watch for: - How much hand-holding you need - Where things break or slow down - What gets your team excited—or makes them groan
Pro Tip:
Time how long it takes to get from zero to “actually useful.” If it takes more than a couple days, that’s a red flag.
Step 5: Compare Real Costs (Not Just the Price Tag)
Vendors love to bury the real costs in fine print or extra modules. Be skeptical.
- Licensing: Is it per user, per seat, or billed some other weird way?
- Add-ons: Are the features you want included, or are they “premium”?
- Implementation: Will you need a consultant or extra training?
- Hidden costs: Will you have to pay for support, integrations, or upgrades?
Add up the actual first-year cost—not just the sticker price.
Step 6: Get Real About Support and Longevity
Even if a tool looks great on day one, you’ll need support when things go sideways. Don’t overlook:
- Support quality: Test it—send a question and see how fast/helpful the response is.
- Documentation: Is it easy to find answers, or is everything behind a paywall?
- Roadmap: Are they actually improving the product, or just coasting?
- Company stability: Will they be around next year? (If they just raised a huge seed round, that’s not the same as profitability.)
Pro Tip:
If the only way to reach support is a chatbot, expect to get frustrated. Look for vendors that make it easy to talk to a human.
Step 7: Get Buy-In From Actual Users
Don’t make this a top-down decision. Even the best tool will flop if your team hates it.
- Involve a few reps in the trial and get honest feedback.
- Ask what they’d miss if you took the tool away after a week.
- Watch for real adoption, not just polite agreement.
If you hear “it’s fine” or “I guess we could use it,” that’s not a win. Look for genuine enthusiasm, or at least relief that something annoying is being fixed.
Step 8: Don’t Overcommit—Start Small and Iterate
You don’t need a five-year contract or a company-wide rollout on day one. Start with:
- A small pilot team
- Short-term contracts or monthly billing, if possible
- Clear success criteria (e.g., “if we book 20% more meetings in 2 months, we’ll expand”)
If it works, scale it up. If not, move on—no shame in that.
What Works (and What Doesn’t)
What works: - Tools that remove friction, not add steps - Solutions that fit your exact workflow - Honest vendors who admit what their product isn’t great at
What doesn’t: - Shiny features that no one uses - Overly complex platforms that need a full-time admin - Buying because “everyone else is using it”
What to Ignore
- “AI-powered” anything, unless you see proof it saves time or closes deals
- Claims of “one-click integration” (they rarely are)
- Industry awards, unless you know who’s doing the awarding
Keep It Simple—And Iterate
Choosing go-to-market software doesn’t have to be complicated. Focus on what your sales team actually needs, test with real users, and don’t be afraid to walk away from tools that don’t deliver. You can always add more later—but it’s way harder to unwind a bad decision. Start small, learn fast, and keep your sales team’s life as simple as possible. That’s what really moves the needle.