You’re leading a B2B team and want real answers about Go-To-Market (GTM) software. You don’t care about buzzwords or shiny dashboards—you want tools that actually help your sales, marketing, and customer success teams work together and hit their targets. Maybe you’ve heard about Letsdive, or your boss dropped the name in a meeting. Either way, you need a clear, honest process for sorting out what’s hype and what’s helpful.
Let’s break down how to actually evaluate GTM software options—so you don’t regret rolling out the wrong tool six months from now.
1. Define What GTM Software Should Actually Solve
Before you look at features or get wowed by demos, nail down your real problems. GTM software is a vague term—it could mean CRM, sales engagement, revenue operations, pipeline analytics, or even team collaboration tools.
Ask yourself and your team: - Where are we losing deals or customers right now? - What processes feel clunky, manual, or error-prone? - Is information falling through the cracks between teams? - Are we missing revenue because we can’t see the full customer journey?
Pro Tip:
Don’t just ask managers. Get input from the actual users—sales reps, marketers, account managers. They’ll tell you where the pain really is.
What to Ignore:
Tons of software promises “end-to-end visibility” or “revenue acceleration.” If you can’t trace that back to a real, specific problem your team has, move on.
2. Map Out Your Must-Haves vs. Nice-to-Haves
It’s easy to fall for big feature lists. Instead, make two short lists:
Must-Haves
- Integrates with your core CRM (Salesforce, HubSpot, etc.)
- Easy for your team to adopt (not just “intuitive”—actually easy)
- Security and compliance boxes checked (GDPR, SOC 2, etc.)
Nice-to-Haves
- Advanced reporting or dashboards
- AI-powered recommendations (if you really need them)
- Collaboration features (chat, notes, etc.)
Honest Take:
AI and automation sound great, but if your team struggles to update notes or log calls, fancy features won’t help. Get the basics right first.
3. Shortlist Tools That Fit Your GTM Stack
You don’t need a “platform” for everything. Some teams work better with a few best-in-class tools that play nicely together.
How to build your shortlist: - List the tools your team already relies on (CRM, email, calendar, chat, etc.) - Filter out any GTM software that doesn’t integrate with these - Check real reviews (not just G2 or Capterra—look for Reddit threads, peer Slack groups, or ask your network)
What about Letsdive?
Letsdive pitches itself as a collaboration and alignment tool for GTM teams. It’s worth considering if you need help breaking down silos and making meetings more actionable. But if your main issue is data quality or pipeline forecasting, you might need something different.
4. Get Hands-On, Not Just a Demo
Don’t trust the sales demo alone. Ask for a free trial or sandbox account. Set up a pilot with real users.
Test for: - How quickly can a new rep get started? - Does it actually reduce manual work? - Can you get the data or reports you need without extra tools? - Does it break anything in your existing workflow?
Pro Tip:
Have at least one skeptic on your pilot team. They’ll spot the gaps and annoyances that true believers overlook.
What to Ignore:
If a tool requires hours of training or a consultant just to get started, be wary. Complexity is rarely your friend.
5. Pressure-Test the Support and Roadmap
GTM software isn’t just about features—it’s about how fast you can get help when things break, and whether the company is actually listening to users.
Ask vendors: - How fast is support? (Test it—send in a ticket.) - What’s on the product roadmap—and how often do they ship improvements? - Can you talk to real customers for references?
Honest Take:
Startups love to promise “white-glove onboarding” and “dedicated CSMs,” but dig into what happens after you’re out of the onboarding phase. If support is slow or the roadmap is a wish list, that’s a red flag.
6. Run the ROI and Change Management Calculation
Buying new GTM software is never just about the subscription cost. Figure out the real impact:
- Implementation time: How much disruption will this cause?
- Training: How long before the team’s up to speed?
- Data migration: Is moving your data quick, or a nightmare?
- Ongoing admin: Will you need someone just to keep it running?
Run a simple calculation:
If it takes 40 hours to roll out but saves your team 10 hours a week, that’s a win. If it’s the other way around, keep looking.
Pro Tip:
Ask the vendor to help you build a simple ROI model with your own numbers—not just the generic “300% ROI!” claims.
7. Reality-Check: What Does Letsdive Do Well (and Not)?
You’re probably still wondering if Letsdive is a fit. Here’s the straight talk:
Where Letsdive shines: - Makes recurring meetings more structured and actionable (agendas, notes, follow-ups) - Useful if your GTM team struggles to stay aligned across sales, marketing, and CS - Integrates with major calendar and communication tools
Where it falls short: - It’s not a CRM or sales engagement platform; you’ll still need those - If your team already runs tight meetings and shares info well, it might be overkill - Advanced analytics or forecasting? Look elsewhere
Bottom line:
If your biggest problem is meetings that go nowhere and scattered action items, Letsdive could be a smart addition. If your problems are elsewhere, don’t force it.
8. Make the Call—But Don’t Overthink It
You’ll never find a perfect tool that does everything. What matters most is picking software that solves your biggest pain today—and that your team will actually use.
- Involve real users in the decision
- Don’t be afraid to start small (pilot with one team, then expand)
- Watch for signs of “tool fatigue”—if your team groans at the idea, pause
Remember:
It’s better to have 80% adoption of a good-enough tool than 20% adoption of something “best-in-class.”
Wrap-Up: Keep It Simple, Stay Flexible
GTM software is supposed to make your team’s life easier—help you close more deals, keep customers happy, and stop dropping the ball. Don’t let shiny features or pushy sales reps distract you from your real needs. Start with your biggest pain points, get hands-on, and bring your team along for the ride.
If Letsdive solves a real problem, great. If not, keep it moving. The best stack is the one your team actually uses—and you can always swap out tools as your business grows. Keep things simple, iterate as you learn, and don’t be afraid to say no to hype.