If you’re in charge of picking sales software for your team, you know the drill: endless demos, big promises, and that creeping feeling you’re about to buy yet another tool that makes things more complicated. This guide is for B2B sales leaders, ops folks, and anyone who wants to actually make their sales process simpler—not just add more stuff. Let’s walk through, step by step, how to cut through the noise and figure out if a GTM (go-to-market) tool like Prosp can actually help, or if you’re better off with something else.
Step 1: Get Clear on Your Sales Process (Don’t Skip This)
Before you even look at software, map out your current sales process. You’d be surprised how many teams skip this and end up with expensive tools that don’t fit how they actually work.
Ask yourself: - Where do leads come from, and how are they qualified? - What’s manual, messy, or always falling through the cracks? - Where does information get lost, delayed, or duplicated?
Pro tip: Grab a whiteboard or a Google Doc and sketch the steps out. Include handoffs between sales, marketing, and customer success. Ugly is fine—clarity matters more.
Why it matters: If you can’t describe your process, no software can fix it. Plus, vendors love to sell you “best practices” that don’t actually fit your business.
Step 2: List Out Your Real Needs (Ignore the Hype)
Every GTM software website talks about “AI-driven insights,” “seamless integrations,” and “next-gen analytics.” Here’s the thing: Most teams only use a handful of features, and the rest just get in the way.
Make two lists: - Must-haves: The stuff you absolutely need, like better lead routing, improved follow-up tracking, or a way to see your pipeline at a glance. - Nice-to-haves: Features that sound good but aren’t deal-breakers. Think predictive scoring, SMS automation, or fancy dashboards.
Watch out for: - Features that solve problems you don’t actually have. - Buzzwords like “AI” or “automation” without clear examples of how they help.
Honest take: If you don’t know why you need a feature, you probably don’t need it right now.
Step 3: Set a Budget—But Don’t Just Look at License Fees
Total cost is about more than the sticker price.
Consider: - License/subscription costs - Onboarding or setup fees - Training time for your team (and lost productivity while they ramp up) - Integration or API costs - Hidden “gotchas” (expensive add-ons, data limits, etc.)
Pro tip: Ask every vendor, “What will this actually cost us in year one if we roll it out to X users? Are there data migration or integration fees?”
What to ignore: Flashy ROI calculators unless you can get real customer references to back them up.
Step 4: Shortlist Tools That Fit Your Workflow (Not the Other Way Around)
Start with your needs and process, not the vendor’s pitch. The best software adapts to you, not vice versa.
For each tool, ask: - Does it work with your CRM, email, and other core tools? - Can you customize workflows without needing an outside consultant? - Are there real-world examples (not just case studies) of teams like yours using it?
When checking out Prosp or any other B2B GTM tool, don’t just look at the feature list. See if it can actually match your sales stages, reporting needs, and handoffs.
Honest take: If a tool forces you to rework your whole process just to fit its way of doing things, it’s probably not a fit—unless your process is truly broken.
Step 5: Run a Hands-On Trial (Don’t Just Watch the Demo)
Vendors love to show you slick demos with perfect data. You want to see what happens when your messy, real-world leads hit the system.
How to run a useful trial: - Set up a sandbox account and load in a week’s worth of actual leads. - Have your team run through a few deals, from qualification to close. - Test integrations with your CRM, email, and marketing tools. - Pay attention to how much manual work is still needed, and where things break down.
Ask your team: - Was it easy to use, or were you clicking around lost? - Did it actually save time, or just add another inbox? - Can you get the reports you need without exporting to Excel?
Red flag: If the trial process feels like pulling teeth, expect rollout to be even worse.
Step 6: Grill the Vendor on Support and Roadmap
Sales software is never “set it and forget it.” You’ll hit issues. You want a vendor who’ll actually help, not just hand you a login and disappear.
Questions to ask: - How fast is support? (Ask for real response time stats, not just “we offer 24/7 support.”) - What’s included for free, and what costs extra? - How often do they update the product, and do they take customer feedback seriously? - Can you talk to a reference customer who started small and grew?
Pro tip: Check online forums or review sites for complaints about support or surprise fees. Every tool has some, but patterns matter.
What to ignore: Vague promises about “customer success” with no specifics.
Step 7: Make Change Management (and Training) Part of the Plan
Even the best software fails if your team doesn’t use it—or worse, uses it wrong.
Keep it simple: - Start with a small pilot group who are open to change. - Cut features you don’t need, at least at first. - Make sure training is hands-on, not just a boring webinar. - Set clear expectations for how and when the tool should be used.
Honest take: If you need a week-long bootcamp just to get started, the tool is probably too complex for most sales teams.
Step 8: Measure, Adjust, and Don’t Be Afraid to Bail
No tool is perfect out of the box. Track what’s actually working—faster response times, fewer dropped leads, more deals closed. If it’s just adding busywork or making things harder, don’t be afraid to cut bait and try something else.
Metrics to watch: - Time from lead to first contact - Number of follow-ups per rep - Pipeline visibility for managers - Rep satisfaction (seriously, ask them)
Ignore: Vanity metrics or “engagement scores” unless they tie directly to real business outcomes.
Keep It Simple and Iterate
Choosing sales software is messy, but it doesn’t have to be overwhelming. Focus on your actual process, ignore the hype, and take things one step at a time. Don’t feel pressured to get it perfect or buy the biggest, fanciest tool. Start with what you need, test in the real world, and tweak as you go. The best sales stack is the one your team actually uses—and that helps them spend more time selling, not fighting with software.