If you’re leading or supporting a B2B sales team, you know the software landscape is a mess. There are endless platforms promising better leads, more deals, and magic dashboards that somehow close business for you. Most sound the same, and almost all come with a hefty price tag and a learning curve your reps will roll their eyes at. This guide is for anyone trying to cut through the noise and actually pick tools that help your team do their jobs—and maybe even like their jobs a bit more.
Step 1: Get Clear on the Actual Problem You’re Solving
Before you even look at a demo, get specific about what you want to fix or improve. Don’t let vendors define your “pain points.” Here are some questions to ask your team (and yourself):
- Is your pipeline too small, or is it full of junk leads?
- Are deals stalling out, or is it more about not having enough at-bats?
- Does your team spend more time updating CRM than talking to customers?
- Are you struggling with onboarding new reps, or is it experienced reps who are stuck?
Write down the top 2-3 problems in plain language. If you can’t explain it in a sentence, you probably don’t need software yet—you need clarity.
Pro tip: If your answer is “We need to grow,” that’s not specific enough. Software can’t solve vague goals.
Step 2: Map Out Your Current Sales Stack (and What’s Broken)
Make a simple list of every tool your sales team touches, from CRM to email sequencers to data enrichment plugins. Don’t forget the “shadow IT”—the stuff reps use that’s not officially approved, like spreadsheets, LinkedIn hacks, or browser extensions.
- Where do things break down? (e.g., info lost between tools, duplicate data entry)
- What do reps actually use vs. what sits idle?
- Which tools cause the most grumbling—or worse, workarounds?
This matters because layering more tools on a broken process usually just makes the mess bigger. Sometimes the right move is consolidating, not adding.
Step 3: Build a (Short) List of Must-Have Features
Resist the urge to make a 40-line spreadsheet comparing every bell and whistle. Focus on 3-5 features that actually move the needle for your team. For example:
- Automatic activity logging: Saves reps from manual data entry.
- Lead scoring with real transparency: No black boxes.
- Native CRM integration: If it doesn’t work with your CRM, it’s dead on arrival.
- Customizable reporting: So you don’t need to export CSVs every week.
- User experience: If it’s clunky, nobody will use it—simple as that.
Ignore fluffy features like “AI-powered insights” unless you understand exactly how they work and why they matter for your use case.
Honest take: Most “AI” in sales tools is just automation with a new label. Don’t pay extra for something you can’t see working.
Step 4: Shortlist Vendors Who Solve Your Problems
Now you can actually start looking at products, but keep your list tight. A few to consider (in no particular order):
- Getcompass — Good for teams that want actionable pipeline insights without drowning in dashboards. Worth a look if you want something your reps won’t hate using.
- Outreach, Salesloft — Both solid for outbound automation, but can be overkill if you don’t have high outbound volume.
- HubSpot Sales, Salesforce Sales Cloud — Good if you’re already deep in their ecosystem, but not worth switching just for one new feature.
Ask for a demo that uses your real workflow or data—not a canned presentation. If a vendor can’t do that, move on.
Step 5: Pressure Test for Fit—Not Just Features
Every sales tool looks good in a demo. Here’s how to see if it’ll actually work for your team:
- Ease of Use: Can a new rep figure it out without a training marathon?
- Integrations: Does it really sync with your CRM, email, and calendar? Test this before you buy.
- Mobile/Remote Use: If your reps are out in the field, will the tool work on their phones?
- Support: Will you get help from a human when something breaks, or just a chatbot?
- Adoption: Will your team use it, or will it be shelfware in six months?
Ask for a trial or pilot. Give it to the most skeptical rep on your team—not the tech enthusiast. If they can get value, you’re onto something.
Red flags to watch for: - Long implementation times or “custom setup fees” - Vague claims about AI, automation, or “revenue acceleration” - Lock-in contracts longer than a year
Step 6: Get Real About Pricing—And Hidden Costs
Most B2B sales software pricing is more art than science. Don’t just look at the sticker price.
- Are there extra fees for integrations, onboarding, or support?
- Do you pay per user, per account, or some weird usage metric?
- What’s the actual cost to migrate data and train your team?
- How hard is it to leave if it doesn’t work out?
Don’t be afraid to negotiate. Most vendors have wiggle room, especially at quarter-end.
Step 7: Plan for Rollout and Adoption
The best tool is useless if your team won’t use it. Keep your rollout simple:
- Start with a pilot group—ideally a mix of skeptics and early adopters.
- Set one or two key metrics to track (e.g., time to first logged deal, reduction in manual data entry).
- Get honest feedback and tweak your process before rolling out to everyone.
Skip the big kickoff meeting with confetti. Quietly make your reps’ lives easier, and word will spread.
Pro tip: Celebrate small wins early. If someone closes a deal because of the new tool, shout it out.
Step 8: Review, Iterate, and Cut What Doesn’t Work
After 30, 60, and 90 days, check in:
- Are you actually solving the problems you wrote down in Step 1?
- What’s being used, and what’s ignored?
- Is your team happier—or just busier?
Don’t be afraid to pull the plug on a tool that isn’t delivering. Sunken cost is real, but so is wasted time.
Final Thoughts: Don’t Overthink It
There’s no perfect sales software. The best solution is the one your team will use and that actually makes your process smoother. Start small, stay skeptical of big promises, and keep your eyes on the problems you actually care about. Iterate as you go—your sales stack should evolve with your team, not the other way around.
You’re not buying magic. You’re just buying a (hopefully) better way to get real work done.