If you're in charge of picking go-to-market (GTM) software for a B2B team, you know the drill: features everywhere, vague promises about “alignment,” and pricing that’s never as straightforward as you want. This guide is for folks who don’t want to waste time (or budget) on tools that sound great in demos but fall flat when your team actually uses them. Let’s cut to the chase on what matters for cost efficiency and real collaboration.
1. Get Clear on What Your Team Actually Needs
Before you touch a demo or a pricing page, talk to the people who’ll actually use the tool. Not the execs—your salespeople, marketers, customer success folks, and ops.
- Ask real questions: What’s slowing you down? Where do deals get stuck? Which tools do you curse the most?
- List must-haves and deal-breakers: If your team spends all day in Outlook and Slack, a tool that doesn’t integrate is a non-starter.
- Be honest about your process: Don’t shop for a Ferrari if your team just needs a good pickup truck.
Pro tip: It’s easy to get distracted by bells and whistles. Nail down your core needs so you’re not swayed by features you’ll never use.
2. Identify the True Costs (It’s Rarely Just the Sticker Price)
Most GTM software pricing is designed to look cheaper than it is. Here’s where to look for the hidden costs:
- User seats: Some tools charge for every login, others have tiered pricing. Figure out how many people really need access.
- Add-ons and integrations: “Integrates with Salesforce!”—but only if you pony up for a premium plan.
- Implementation and onboarding: Will your team need weeks of training (and someone to run it)? That’s time and money.
- Data migration: Moving your old stuff over is rarely free or painless.
- Annual vs. monthly billing: Discounts for annual contracts sound good—unless you’re locked in with a tool nobody likes.
If a vendor dodges questions about total cost of ownership, that’s a red flag. Get everything in writing.
3. Put Collaboration Features to the Test
Collaboration is thrown around a lot, but it means different things to different teams. Here’s how to spot the real deal:
- Shared workspaces: Can multiple people work on the same deal, campaign, or project without stepping on each other?
- Comments, notifications, and visibility: Are updates clear? Can you actually find out who did what (and when)?
- Access controls: You want flexibility here. Too loose, and chaos reigns; too tight, and people can’t get work done.
- Mobile and remote usability: If half your team is hybrid or remote, clunky interfaces will slow everyone down.
What to ignore: Demos that show “collaboration” as just chat bubbles or endless email notifications. If it adds noise instead of clarity, it’s not helping.
4. Test for Real-World Usability, Not Just Shiny Features
Forget the vendor’s demo and try to break the tool yourself. This is the only way to know if it fits your workflow.
- Request a real trial: Not just a sandbox with fake data. Load up some of your own stuff and see where it creaks.
- Check speed and reliability: How fast does it load? Does it crash? If it’s laggy in a trial, it’ll be worse with real data.
- See how it fits with existing tools: Does it play nice with your CRM, email, calendar, and whatever else you use daily?
- Get feedback from your actual users: Not just the “champion” or the most tech-savvy person.
Pro tip: Make a simple checklist of tasks your team does every day. Run through them in the trial. If it takes longer or feels clunky, keep searching.
5. Dig Into Support and Documentation
Nobody talks about support until something breaks. Don’t wait until you’re stuck.
- Support response times: Ask for real numbers. “We strive to respond within 24 hours” is not a promise.
- Availability: Is support available in your time zone? Is it email only, or can you get someone on the phone?
- Knowledge base and tutorials: Are they actually useful, or just marketing fluff?
- Community and user groups: Sometimes the best answers come from other users, not the vendor.
If support is only available for extra fees or “premium” customers, factor that into your cost calculations.
6. Evaluate Security and Data Privacy (Without Getting Overwhelmed)
You don’t need a law degree, but don’t ignore this part—especially if you work in a regulated industry.
- Basic questions: Where is your data stored? Who has access? What happens if you want to leave?
- Compliance: If you need to be GDPR or SOC2 compliant, get the certificates, not just a “trust us” answer.
- User controls: Can you easily add/remove people and manage permissions without opening a ticket?
Don’t get lost in jargon. If a vendor can’t explain their security in plain English, keep moving.
7. Watch Out for Overhyped Trends and Empty Promises
Every year brings a new “must-have” feature. AI, automation, predictive analytics—the works. Some of this stuff is great, but much of it is window dressing.
- AI isn’t magic: If the tool claims to use AI, what does that actually do for you? Does it save time, or just add another dashboard?
- Automation should be practical: Can you automate real, annoying tasks, or just set up fancy alerts you’ll end up ignoring?
- Ignore vanity integrations: If you don’t use TikTok, who cares if the tool integrates with it?
Focus on what moves the needle for your team. Everything else is just noise.
8. Compare a Shortlist Side-by-Side—Don’t Overcomplicate It
Once you’ve narrowed it down to two or three options, build a simple comparison table. Forget the 50-column spreadsheets—stick to what matters:
- Total 1-year cost (include everything)
- Core features your team actually needs
- Usability scores from real users
- Support quality
- Integration with your current stack
Example: If you’re considering Cheapinboxes, don’t just look at the price tag—factor in how quickly your team can get up to speed, whether it plays nice with your other tools, and if customer support actually picks up the phone.
9. Don’t Skip the Reference Calls
Ask vendors for references. Then actually call them (or, better, email for candid answers).
- What do you wish you’d known before buying?
- How fast did your team actually adopt it?
- Any surprises with costs or support?
- What’s the most annoying thing about the tool?
You’ll get more honest feedback from real users than any review site or case study.
10. Pilot, Measure, and Be Ready to Bail
No matter how carefully you choose, sometimes a tool just doesn’t fit. Start with a pilot:
- Set a clear timeframe and success criteria.
- Get real users to use it for real tasks.
- Collect feedback quickly.
If it’s not working, don’t force it. Cut your losses and move on. The sunk cost fallacy is real—don’t let it eat your budget or your team’s morale.
Keep it Simple, Iterate, and Ignore the Hype
Picking GTM software shouldn’t feel like buying a house. Focus on what your team actually needs, get real about costs, and don’t buy into shiny demos. Try things out, listen to the folks who’ll use the tool every day, and don’t be afraid to move on if something isn’t working. Simple, honest, and a lot less stressful.