If you’re responsible for picking sales tools for a B2B team, you know the drill: every week, a new “game-changer” lands in your inbox. Demos, case studies, and promises to double your pipeline—most of it’s noise. Choosing the right go-to-market (GTM) software for your sales team shouldn’t feel like buying a used car. This guide is for sales leaders, ops folks, and anyone who actually has to use these tools day in and day out.
Let’s walk through how to evaluate B2B GTM tools like Handwrite without getting swept up in the hype, so you can find something that genuinely helps your team win more deals (and doesn’t end up as shelfware).
1. Know What Problem You’re Actually Trying to Solve
Before you even look at a vendor website, get clear on the pain points. Be specific. “Increase pipeline” or “better personalization” is too vague.
Ask yourself: - Where are reps actually losing time? (Be honest—ask them.) - Are deals stalling out at a certain stage? - Is data entry a nightmare? Is outreach generic and ignored? - Are you chasing a volume problem, or a quality problem?
Pro tip: If you can’t explain in one sentence what you want the tool to fix, you’re not ready to evaluate anything yet.
2. Make a Short List of Must-Have Features (Not a Wishlist)
It’s easy to get dazzled by slick dashboards and AI promises. Instead, write down 3-5 non-negotiable features, like: - Native integration with Salesforce (and not via a third-party plugin) - Ability to automate personalized outreach at scale, but with real customization (not just {FirstName} tags) - Clear tracking of rep activity and outcomes
Ignore: - Features your team will never use - Overly broad “all-in-one” promises that rarely deliver - AI “insights” that sound cool but don’t tie back to your actual workflow
Reality check: Most sales teams use about 20% of any tool’s features. Focus on the core.
3. Demo Like You Mean It: Get Hands-On, Not Just a PowerPoint
Vendors love to walk you through their “happy path.” You need to see how the tool works for your real-world use case.
When demoing a tool like Handwrite: - Ask to use your own data or a realistic sample set - Have a rep (not just an admin) try it live—can they get value in 15 minutes? - Break something on purpose: What happens if you make a mistake? Is it easy to recover? - Look for clunky steps, confusing screens, or places where your team will get lost
Red flag: If the vendor won’t let you test drive with your own hands, move on.
4. Dig Into Integration and Workflow Fit
A tool isn’t just another app—it’s a new step in your team’s day. If it doesn’t slot in easily, it won’t get used.
Check: - Does it sync with your CRM (not just push data in, but update and pull back out)? - How does it handle duplicate data or errors? - Does it break your reporting? - Does it force you to change your sales process, or does it fit what you already do?
Talk to your ops or IT folks early. Nothing kills a rollout faster than finding out you need a month of custom development just to get going.
Pro tip: Ask for a list of customers with your exact CRM and workflow setup—then actually talk to them.
5. Price Out the Real Cost (Not Just the Subscription)
Vendors will quote you a per-seat price, but that’s only part of the story.
Consider: - Setup fees, onboarding, and required “professional services” - Ongoing admin work—who’s maintaining this thing? - Training time for reps - How hard is it to switch or get your data out if you change your mind?
Some tools are cheap up front but cost a fortune in hidden headaches. Others are expensive but save you so much time they pay for themselves. Run the numbers honestly.
6. Don’t Fall for Shiny AI Promises (Yet)
A lot of GTM tools now use AI as a buzzword. Sometimes it means “actually helpful automation,” but often it’s just lipstick on a spreadsheet.
Be skeptical of: - Claims that AI will “write emails for you” that somehow sound human - Scoring and insights that aren’t transparent or can’t be explained by the vendor - “Personalization at scale” that spits out robotic, obviously templated messages
Ask to see real examples—ideally, output that’s been used by actual customers in your industry. If it feels generic or forced, your prospects will spot it a mile away.
7. Check References—But Ask the Right Questions
Customer references are usually hand-picked by the vendor. Don’t just ask “are you happy with it?”
Instead, dig into: - What did onboarding really look like? - How long before reps actually used it without hand-holding? - What’s annoying? What do they wish they’d known before buying? - How does support handle issues? Are bugs fixed quickly?
If you can’t talk to a reference who matches your team size, industry, and tech stack, be wary.
8. Pilot With a Small Group—And Define Success Up Front
Don’t buy for the whole team right away. Run a pilot with a few reps who’ll actually use it.
Set clear criteria for success, like: - Reps send 2x more personalized messages per week with no drop in quality - Follow-up rates increase by X% - Admin time drops by Y hours per week
Track what actually changes. If the tool creates more work or confusion, it’s not worth rolling out to everyone.
Pro tip: Get honest feedback from the most skeptical reps. If you can win them over, you’re onto something.
9. Watch for Shelfware and Tool Creep
Even good tools can end up collecting dust if they’re not part of your team’s daily flow. Set a reminder to check usage numbers after 30, 60, and 90 days.
If adoption is low: - Is the tool too complex, or just not helpful enough? - Did you get buy-in from the team, or was it forced on them? - Can you simplify or automate setup to remove friction?
Don’t be afraid to pull the plug on something that isn’t working. Better to cut losses than keep paying for a tool nobody touches.
10. Keep It Simple—And Iterate
The best GTM stack isn’t the one with the most logos on your vendor slide. It’s the one your team actually uses, every day, to move deals forward.
- Don’t try to solve every problem at once
- Start with tools that address a real, painful bottleneck
- Revisit your stack every quarter—what’s working, what’s not?
Most importantly, listen to your reps. They’re the ones who’ll tell you, directly or indirectly, if you picked a winner or just added more noise.
Bottom line: Don’t let hype or FOMO drive your buying decisions. Get clear on your needs, test tools ruthlessly, and remember—no tool will fix a broken process. Keep it simple, stay honest about what’s working, and don’t be afraid to change course. That’s how you build a stack that actually helps your team sell more (and keeps your sanity intact).