Sales and revenue tech is a zoo. If you’re tasked with picking software to help your revenue team actually close more deals, you’ve got hundreds of Go-To-Market (GTM) tools claiming to do everything but make coffee. It’s easy to get overwhelmed—especially when every vendor says they’re “AI-powered” and “the only platform you’ll ever need.”
This guide is for sales and revenue leaders, ops folks, and even skeptical reps who just want the right tool for the job. Whether you’re looking at Setsail or a dozen other options, here’s how to cut through the hype, compare your choices, and pick what’ll really move the needle.
1. Start With Problems, Not Features
Before you even look at vendor websites, get brutally clear on what you actually need. GTM software is supposed to help you sell more, faster—or at least make it less painful. That means:
- Figure out where your current process is broken. Are reps wasting time on manual data entry? Is forecasting a mess? Are deals stalling for mysterious reasons?
- Prioritize your headaches. Not every problem is equally important. Fix the biggest pain first.
- Write down your “must-haves” (what you need) and “nice-to-haves” (what you want).
Pro tip: If you can’t get agreement on your top 3 problems, don’t buy anything yet. More tech won’t fix fuzzy thinking.
2. Build a Shortlist That Matches Your Needs
There are hundreds of B2B GTM tools out there—don’t waste time on all of them. Focus on the categories that actually map to your problem.
Common GTM tool categories: - Pipeline management: Track deals, spot risk, forecast revenue. (Examples: Setsail, Clari, InsightSquared) - Sales engagement: Automate outreach, sequences, follow-ups. (Examples: Outreach, Salesloft) - Conversation intelligence: Analyze calls and meetings. (Examples: Gong, Chorus) - Revenue intelligence: Pull in signals from email, calls, CRM to find what drives sales. (Setsail is in this camp.) - Enablement/Content: Give reps the right decks, case studies, and training. (Examples: Highspot, Showpad)
How to shortlist: - Toss out anything that doesn’t solve your key problems. - Check integrations. If it won’t talk to your CRM or email, it’s dead on arrival. - Look at what your peers use. Not always gospel, but it helps weed out the duds.
Honest take: Ignore the “all-in-one” promises if you can’t see how they solve your specific pain points. Jack-of-all-trades tools often end up as master of none.
3. Compare by Outcome, Not Demos
Vendors love shiny demos. But what matters is what you get after the honeymoon phase.
Questions to ask: - Does this actually help reps close more deals—or just create more dashboards? - How fast will we see results? (If it takes six months to get value, beware.) - What measurable outcomes have their customers seen? (Look for proof, not just testimonials.) - What’s the real cost—including setup, training, and who will run it day-to-day?
Honest take: Some tools look amazing in the demo but need an ops team just to keep them running. If you’re a lean team, that’s a problem.
4. Dig Into Data Quality and Automation
Revenue tools are only as good as the data they have. Garbage in, garbage out. Here’s what to check:
- Automatic data capture: Does the tool pull in emails, meetings, and calls automatically, or does it rely on reps to log everything? (Hint: manual logging almost never works.)
- Data accuracy: How does it handle duplicates, missing info, or bad data from your CRM?
- Customization: Can you tweak what gets tracked, or is it one-size-fits-all?
- Reporting: Are insights actionable, or just more noise?
Setsail’s angle: Setsail focuses on capturing activity signals automatically and mapping them to deal outcomes. If your team struggles with manual CRM updates or you want to know what actually moves deals forward, this is worth a close look. But, if your data sources are a mess, no tool—including Setsail—can magically clean it up overnight.
5. Check Integration and Workflow Fit
A tool that doesn’t play well with your stack is going to cause headaches.
- CRM integration: Does it support your CRM (Salesforce, HubSpot, etc.) out of the box?
- Email/calendar: Can it pull signals from Gmail, Outlook, etc.?
- APIs and export: If you need to get your data out, how easy is it?
- User experience: Is it intuitive, or will you need to force reps to use it?
Pro tip: Get hands-on. Don’t rely on the vendor’s walkthrough—have your own team poke around. Clunky interfaces kill adoption.
6. Understand Pricing—and the Hidden Costs
GTM tools love to hide their true costs behind “custom pricing” or “platform fees.”
- Licensing: Per user, per seat, or flat fee? Does it scale with your team?
- Implementation: Is onboarding included? Who does the heavy lifting?
- Training and support: Is there ongoing help, or do you pay extra?
- Contract terms: Can you start small, or do they want a long-term commitment up front?
Honest take: Beware of tools that need an “admin” or “success plan” just to keep them working. That’s more overhead than most teams want.
7. Look for Real Results, Not Just Reference Logos
Every vendor has a wall of customer logos. What you want is proof the tool actually helps teams like yours.
- Case studies: Are there real results with numbers, timelines, and pain points similar to yours?
- User reviews: Check sites like G2 or TrustRadius—but read between the lines for the negatives.
- Talk to customers: Ask the vendor for reference calls, but try to find your own contacts if you can.
Pro tip: Ask references, “What don’t you like?” and “What do you wish you’d known before buying?”
8. Don’t Underestimate Change Management
Even the best tool is useless if your team won’t use it.
- Adoption: How easy is it for reps and managers to actually use day-to-day?
- Training: Is the vendor’s training any good, or will you need to make your own materials?
- Support: Is support responsive and knowledgeable, or slow and generic?
Honest take: The best software fades into the background and just works. If you’re worried about adoption, run a trial with real users before committing.
9. Run a Real-World Pilot
If you’re down to a couple of finalists, don’t just pick based on slide decks.
- Pilot with real deals: Use your actual pipeline and team, not a sandbox full of test data.
- Set success criteria: What would make this a win? Be specific.
- Measure results: Did it save time, surface new insights, or help close deals?
- Get feedback: What did reps and managers like? What did they hate?
Pro tip: Vendors who resist running a pilot or want to charge a fortune for it usually know their tool won’t prove its worth.
10. Make the Call—And Keep It Simple
Once you’ve got the data, pick the tool that solves your biggest problems with the least hassle. It won’t be perfect, but that’s fine. The goal is to get value soon, not to find “the best” solution for every possible scenario.
A Few Final Thoughts
GTM software can make your revenue team’s life a lot easier—but only if you pick based on your real needs, not on buzzwords or peer pressure. Don’t let vendors or internal politics overcomplicate things. Start with your biggest pain, insist on proof, and remember: you can always switch tools later if something’s not working.
Keep it simple, iterate fast, and don’t buy promises. Buy outcomes.