If picking B2B go-to-market (GTM) software feels like running an obstacle course blindfolded, you’re not alone. Sales, marketing, ops, and customer success all want different things, and every vendor swears their tool is the answer. This guide is for anyone tasked with finding GTM software that actually helps cross-functional teams work together—without becoming another expensive shelfware experiment.
1. Get Real About Your Team’s Actual Problems
Before you look at a single demo, get brutally honest about what’s broken or slow in your GTM process. Don’t default to “we need AI” or “let’s automate everything.” Ask the people who’ll use the tool:
- Where do deals get stuck?
- What’s a pain to report or track?
- Who’s always out of the loop?
- What’s wasting your team’s time?
Write these down, and make them your must-haves. If a tool doesn’t address at least one, it’s not worth your time—no matter how shiny it looks.
Pro tip: Don’t get distracted by features you “might” use someday. Focus on the 2-3 things that’ll make your team’s life easier this quarter.
2. Map Out Who Needs to Use (and Benefit From) the Tool
Cross-functional means you’ll have sales, marketing, maybe even product and customer success poking around. If the tool only helps one group, you’ll end up with silos—or endless bickering.
- List out everyone who’ll need to touch the tool—by role, not just department.
- Ask each group: “How will this help you do your job better?”
- Watch out for tools that claim to “do it all” but really just cater to one persona.
What usually works: Tools that make sharing info and collaborating dead simple, without a bunch of training or workarounds.
What to ignore: Overly complex “platforms” that require consultants just to get started. If your team needs a manual to log in, move on.
3. Make Integration a Non-Negotiable
Your GTM process already runs on a messy mix of CRM, email, spreadsheets, and more. Any new software must fit into that reality—otherwise, you’re just creating more work.
- Ask vendors to show real integrations with your core systems (Salesforce, HubSpot, Slack, etc.).
- Look for two-way sync, not just “we can export a CSV.”
- Check how easy it is to actually set up and maintain these connections—don’t trust “it’s on our roadmap.”
Pro tip: If the integration demo is “coming later” or only works via Zapier hacks, be skeptical.
4. Dig Into Usability—Not Just UI
A slick interface is nice, but if your team can’t figure out how to use the tool day-to-day, it’ll just gather dust.
- Ask for a trial or sandbox. Get a couple of real users to try it for a week.
- Time how long it takes to do common tasks (updating deal info, sharing feedback, pulling a report).
- Watch for “hidden” friction: extra clicks, confusing menus, or screens that only a power user could love.
What works: Tools that don’t require hours of onboarding or endless training videos. If someone can’t pick it up in 30 minutes, it’s too complicated.
What to ignore: Demo environments that are pre-loaded with perfect data. Ask to see how it handles messy, real-world info.
5. Separate Hype From Reality on “AI” and Automation
Every vendor claims their software is “AI-powered” or “automates everything.” Most of the time, that means little more than basic rules or generic analytics.
- Ask exactly what the AI does—and how it’ll save users time or make better decisions.
- Request concrete examples: “Show me how this flagged a real deal risk,” not just “we use machine learning.”
- Be wary of automation that’s hard to customize or creates more alerts than it solves.
What works: Automation that takes boring, repetitive work off your team’s plate—like auto-logging emails or flagging missing contacts.
What to ignore: Vague “predictive insights” that don’t tie to your actual pipeline or deals.
6. Check Collaboration Features—But Don’t Overthink It
Good collaboration means people can comment, share updates, and flag issues without switching tools or losing context. But don’t get lost in endless “collaboration suite” promises.
- Look for: threaded comments, tagging teammates, simple sharing with context.
- Avoid: generic chat features, or anything that tries to replace Slack or Teams.
- Make sure updates and feedback are visible in the flow of work—not buried in notifications nobody reads.
Pro tip: The best collaboration features feel invisible. If your team has to “learn” how to collaborate, the tool’s probably not a fit.
7. Compare Reporting and Visibility—But Don’t Buy a BI Tool
Everyone wants better pipeline visibility, but most B2B GTM tools overpromise here. Ask for:
- Out-of-the-box reports that map to your core KPIs.
- The ability for non-technical users to pull and share reports themselves.
- Customization that doesn’t require a data analyst.
What works: Dashboards and reports your team actually understands and uses. If it needs a walkthrough every time, it’s too complex.
What to ignore: Endless customization options that sound great but just lead to analysis paralysis.
8. Do the Math—Total Cost (and Hidden Costs)
It’s easy to get lost in monthly pricing, but the real cost includes setup, training, integrations, and the time your team spends getting up to speed.
- Ask about all add-ons, usage limits, and “premium” features.
- Factor in how much time your admin or ops team will spend managing the tool.
- Check for contract minimums or auto-renewal gotchas.
Pro tip: If pricing is “let’s set up a call,” assume you’re in for sticker shock.
9. Get Real-World References and Proof
Case studies are nice, but you want to talk to teams like yours who are actually using the tool.
- Ask vendors for 2-3 references with similar team size, industry, and use case.
- Questions to ask references:
- What’s actually improved since you started using the tool?
- What’s still a headache?
- How was onboarding—really?
- Be wary of reference calls where the customer is joined by the vendor (yes, this happens).
What works: Honest feedback from users who’ve stuck with the tool for at least a year.
10. Pilot, Iterate, and Stay Skeptical
Don’t buy on a demo. Set up a short pilot—ideally 30 to 60 days—with a small but representative team. Make sure you:
- Set clear success criteria tied to your pain points from Step 1.
- Get feedback weekly—what’s working, what’s frustrating, what’s missing?
- Be ready to walk away if it’s not delivering. Sunk cost is not a strategy.
Want an example of a tool that gets a lot of this right? Factors is built for cross-functional sales teams and focuses on actionable insights, not just dashboards. Worth a look if you want something that works out of the box.
Keep It Simple (and Don’t Wait for Perfect)
Picking B2B GTM software for cross-functional teams isn’t about finding the “best” tool—it’s about finding what actually solves your team’s current headaches, fits into your workflow, and gets adopted. Ignore the hype, focus on what matters, and remember: you can always change or upgrade later. Start simple, get feedback, and keep moving. The perfect tool doesn’t exist—but the right one for right now probably does.