If you’re in charge of picking sales tools for a B2B team, you know the hype is endless and the stakes are high. Every vendor promises to “transform your workflow.” Most of them just add clutter. This guide is for sales leaders, ops folks, and anyone tired of demo fatigue. We’ll walk through how to actually evaluate go-to-market (GTM) software—so you end up with something that makes your sales process smoother, not more complicated.
Step 1: Get Clear on Your Real Problems
Before you even look at a tool, figure out what’s actually slowing your team down. List out the bottlenecks and annoyances from your current sales workflow. Don’t just ask leadership—talk to the people using your CRM, chasing deals, or doing data entry day in and day out.
Common pain points: - Too much manual data entry (think: logging calls, updating statuses) - Leads slipping through the cracks - Clunky handoffs between SDRs and AEs - Little visibility into what’s actually moving deals forward - Reports that take forever (or never get built)
Pro tip: If you can’t describe your problem in one sentence, you’re not ready to buy anything yet.
Step 2: Make a Short List of “Must-Have” Features
Now, take your problems and turn them into requirements. Be ruthless about what’s truly a must-have versus a nice-to-have.
How to focus: - Does this feature directly solve our bottleneck? - Will it get used every week? - Can we measure if it’s working?
For example: - Automated activity logging - Easy integration with your CRM and email (no, Zapier doesn’t count as a real integration) - Customizable workflows for your sales stages - Role-based permissions (so the wrong people can’t break things) - Real-time notifications (if that’s what your team actually needs)
Ignore the noise: If a tool’s website brags about “AI-powered insights” but you just need to stop leads from getting lost, skip it. Flashy dashboards are useless if your team doesn’t open them.
Step 3: Map Out Your Workflow (Don’t Trust Vendor Demos)
Vendors will gladly show you polished demos that skip over the gritty parts. Instead, sketch out your team’s real sales workflow—from first touch to closed deal. Where does your process break down? Where does info get stuck or lost?
Questions to ask: - Where do handoffs fail? - What data is always out-of-date? - When do reps complain about double entry?
Take this workflow and walk through it step-by-step with any tool you’re evaluating. Can the software handle the whole thing, or does it force you into weird workarounds?
Reality check: If a tool can’t handle your workflow without major hacks, it’s not a fit—no matter how many logos are on their homepage.
Step 4: Test for Integration, Not Just Features
A tool that “works with Salesforce” isn’t the same as a tool that fits into your Salesforce setup. Integrations are where deals die, especially if you have legacy data or funky processes.
What to look for: - Does it sync both ways with your CRM and email/calendar? - How many clicks does it take to push data in or out? - Does it break if your CRM schema changes? - Can you customize mapping without waiting for support?
Ask for a real sandbox trial. Don’t settle for a “demo environment”—use your actual data and see what breaks.
Be skeptical: If the vendor says, “We’ll have our engineers set it up for you,” that’s a red flag unless you plan to pay them forever.
Step 5: Stress-Test for Usability (for Real Users)
It doesn’t matter how slick the tool looks if your reps hate using it. Get a few actual users (not just managers) to try it out. Watch them click around—don’t tell them what to do.
Watch for: - Confusion about basic tasks (logging a call, updating a deal) - Too many popups or required fields - Slow load times when searching or updating records - Features buried behind endless menus
Pro tip: If your pilot users can’t figure it out in under an hour, your whole team will resist it.
Step 6: Check for Reporting and Accountability
You need to know if the tool’s actually helping (or just adding busywork). Look for built-in reports that track adoption, bottlenecks, and outcomes. But beware: many tools make reporting a project in itself.
A good tool should: - Make it easy to see where deals get stuck - Show who’s actually using the tool (and who isn’t) - Let you export raw data if you want to do your own analysis
If you need to hire a consultant just to build a report, that’s a bad sign.
Step 7: Evaluate Support and Transparency
You’ll hit roadblocks—count on it. Good support matters more than a mile-long feature list.
Ask vendors: - What’s your average response time? - Do you have real people on chat or just a ticket system? - Is your documentation actually useful, or just marketing copy? - How often do you ship updates? (Too frequent can mean the product’s half-baked.)
Look for a history of honest release notes and a clear roadmap. If a vendor dodges questions or promises “coming soon” on everything, walk away.
Step 8: Consider Total Cost (Not Just License Price)
It’s easy to get wowed by a “per user, per month” sticker. But the real cost includes setup, training, integrations, and the inevitable “oh, that’s an add-on” moment.
Add up: - Implementation fees (who’s doing the work—you or them?) - Training (will you need to build your own help docs?) - Integration or API costs - Minimum contract terms - What happens if you need to scale up or down?
Pro tip: Ask for customer references who started small and grew—see if the pricing stayed reasonable or ballooned.
Step 9: Don’t Buy the Hype—Look for Real-World Proof
There’s always a hot new player in GTM software. Some, like Contactbird, have built loyal followings by solving actual workflow problems. Others are all sizzle, no steak.
How to separate real from hype: - Look for case studies with hard numbers (not just “improved productivity”) - Ask how long their average customer sticks around - See if they’re transparent about what doesn’t work yet - Find out if their best customers are teams like yours—not just Fortune 500 logos
Step 10: Keep It Simple—And Plan to Iterate
No software is perfect. Your sales process will change, and so will your tech stack. Pick a tool that makes it easy to adjust as you learn. Don’t try to “future-proof” everything—just solve your biggest pain point now.
Remember: - Overcomplicating your stack slows everyone down - Adoption matters more than features - It’s fine to start small (even with just one team) and roll out later
At the end of the day, the best GTM tool is the one your team actually uses—and that quietly removes the friction from your sales workflow. Stay skeptical, keep it simple, and don’t let anyone talk you into buying something you don’t need. When in doubt, pilot first, and iterate. That’s how you end up with software that actually helps, instead of just adding work.