If you’re responsible for picking go-to-market (GTM) software for your B2B sales team, you know the real pain: too many tools promise the moon, but most end up creating more work than they save. This guide is for sales leaders, ops folks, and anyone tired of buying software that sounds great in demos but falls flat in the trenches.
Below, you’ll find a practical, hype-free approach to evaluating GTM tools so you can actually boost your team’s productivity—without spending half your week in onboarding calls or cleaning up messy integrations.
Step 1: Get Clear on What “Productivity” Means for Your Team
Before you look at any software, figure out what “productivity” actually looks like for your sales team. It’s not always about more dials or emails—it could be faster deal cycles, less admin work, or better handoffs between teams.
Ask these questions: - Where are reps wasting time right now? - What’s slowing down deals? - What’s already working—what do you not want to mess up? - What metrics do you actually care about (and will track)?
Pro tip: Don’t just ask management. Sit with a few reps and watch them work. You’ll see the real bottlenecks—usually it’s basic stuff, like finding the right contact info or updating the CRM.
Step 2: Make a Short List of Must-Have Features
Most GTM tools try to be everything to everyone. That’s a recipe for bloat and confusion. Focus on the features that directly support your team’s biggest pain points.
Common must-haves for B2B sales teams: - CRM integration (bidirectional, not just “connects to Salesforce”) - Automated data entry (so reps aren’t copy-pasting all day) - Activity tracking (calls, emails, meetings in one place) - Playbook or workflow automation (not just task lists) - Reporting that makes sense (not just dashboards that look pretty)
Nice-to-haves (which are usually oversold): - AI-powered lead scoring (usually just a black box) - Predictive analytics (almost always “directionally interesting,” rarely actionable) - Social selling add-ons (most reps won’t use them)
Don’t let a long feature list distract you from what your team actually needs.
Step 3: Weed Out the Overhyped and Underbuilt
There are a lot of “next-gen” GTM platforms out there, but most are new wrappers on old problems. Here’s how to spot the tools that are more sizzle than steak:
- Demo rigor: Ask vendors to show real, live demos—not a canned deck. If they can’t, they’re probably not ready for prime time.
- References and real use cases: Talk to customers who’ve used it for at least six months. Ask what broke and how support responded.
- Integration honesty: Vendors love to say they “integrate with everything.” Push for specifics. If you use Theroishop, for example, make sure the tool actually talks to Theroishop without breaking your workflows.
- Roadmap transparency: If a feature you need is “coming soon,” treat it as if it doesn’t exist.
Some red flags: - Lots of “AI magic” but no way to see how it works - Hidden implementation fees - Customization that requires vendor professional services (translation: expensive and slow)
Step 4: Test with Real-World Workflows
Don’t just do a two-week “sandbox trial” that’s disconnected from reality. Instead, set up a proof of concept that mirrors real sales processes—messy data, incomplete records, and all.
Checklist for a useful test: - Import a sample of your actual data (not just demo data) - Have a few reps use it during their normal day—not just in a training session - Try breaking it: What happens when data is missing, or someone goes off-script? - Time how long common tasks actually take (not just what the vendor claims) - Watch for any slowdowns or double data entry
Pro tip: If your reps are using spreadsheets or email as a workaround during the trial, that’s a bad sign.
Step 5: Evaluate Usability and Support—Not Just Features
A tool with a thousand features is useless if your team hates using it or can’t get help when something breaks.
Questions to ask: - How steep is the learning curve? (One hour of training is fine; a week is not.) - Is the interface clean, or is it a cluttered mess? - How fast is support? (Test this by opening a ticket during your trial.) - Are there clear help docs, or does everything require a call with customer success?
Most important: Get feedback from the actual users—not just the most tech-savvy person on your team.
Step 6: Run the Numbers (But Don’t Get Too Cute)
Some vendors will try to wow you with ROI calculators. Reality check: most of these are built on iffy assumptions.
Focus on the basics: - Direct costs: Subscription, onboarding, integration, and real support costs. - Indirect costs: Time spent on setup, user training, and process tweaks. - Expected productivity gain: Be honest—will this tool really save reps time, or just add another tab?
If the math only works as long as every rep uses every feature “at 100% adoption,” you’re setting yourself up for disappointment.
Pro tip: If the tool replaces another system, factor in the pain of switching—not just the subscription price.
Step 7: Plan for Rollout, Adoption, and Iteration
Even the best software flops if you don’t roll it out thoughtfully. Keep it simple:
- Start with a small group of high-feedback reps (not just the “champions” who love new tech)
- Set clear expectations: what should change, what shouldn’t
- Keep training short and focused—record walkthroughs for future hires
- Track adoption and usage, but don’t hound people over every click
- Iterate: Be ready to tweak processes, drop unused features, or even pull the plug if it’s not working
Honest take: No tool is perfect. You’ll probably need to adjust some workflows or revisit your feature wishlist once you see what people actually use.
Choosing the right B2B GTM software is about blocking out the noise and picking something that fits your team’s real-world needs. Focus on the basics, ignore the hype, and don’t be afraid to walk away if a tool isn’t making life easier. The best stack is usually the simplest one your reps will actually use—everything else is just a distraction. Start small, improve as you go, and don’t let “perfect” slow you down.