If your sales team is growing, you’ve probably noticed: there’s a sea of B2B software promising to “revolutionize your go-to-market strategy.” Most of it sounds the same—until you’re locked into a contract and realize you’re missing half the features you actually need. This guide is for sales leaders, ops folks, and founders who want to pick the right tools without wasting time or money.
Step 1: Know What “Go To Market” Tools Actually Do (and Don’t Do)
“Go to market” (GTM) tools are a grab bag. They might include:
- CRM systems (think Salesforce, HubSpot)
- Sales engagement platforms (Outreach, Salesloft)
- Lead enrichment and data tools (ZoomInfo, Apollo)
- Pipeline analytics and forecasting (Clari, InsightSquared)
- Proposal and contract tools (PandaDoc, DocuSign)
- Territory planning and routing (Xactly, MapAnything)
- Conversation intelligence (Gong, Chorus)
What they DON’T do: They don’t magically make your team better at selling. No tool replaces clear strategy, solid process, or good hiring. At their best, these tools save time, stop data chaos, and help you spot patterns faster. At their worst, they’re expensive distractions.
Pro tip: If you can’t explain in one sentence why you need a new GTM tool, you probably don’t need it yet.
Step 2: Get Clear on Your Use Cases (Not Just Features)
Don’t start with vendor feature lists. Start with your team’s real, painful problems. Ask yourself:
- Where are reps losing time or dropping the ball?
- What data or process gaps keep turning into firefighting?
- Are you missing out on deals because of slow response or poor follow-up?
- Do you need better forecasting, or is pipeline visibility fine?
Write down your top 3-5 needs. Be specific—“automate outbound emails,” “see real-time pipeline changes,” “track contract status,” etc.
What to ignore: Shiny features you see in demos but don’t solve your team’s actual problems. If it doesn’t map to a use case, skip it.
Step 3: Map the GTM Stack You Already Have
Before you add anything, take stock. List your current tools, including the ones no one likes or uses. Common culprits:
- CRM (usually the core system)
- Spreadsheets (yes, they count)
- Email/Calendar (Gmail, Outlook)
- Proposal platforms
- Anything reps use outside the CRM (Slack, Notion, even sticky notes)
Draw a rough diagram—whiteboard or napkin sketch is fine. See where your pain points are. Sometimes, the real issue is how tools fit together (or don’t).
Pro tip: Sometimes a “new tool” is just better training or cleaning up your existing setup.
Step 4: Shortlist Based on Must-Haves, Not “Nice to Haves”
Now that you know your real needs and current stack, filter options using your must-haves. Think:
- Does it integrate with your CRM (for real, not just in theory)?
- Can your team actually use it, or is it too complex?
- Does it solve your top-3 problems from Step 2?
Don’t get distracted by features you might use one day. If a tool claims to be “all-in-one,” ask which parts actually work well. For example, Extrovert promises tight CRM integration and fast onboarding—dig into whether that’s true for your setup.
What to ignore: Fancy dashboards you won’t look at, AI features that sound cool but don’t work, and “top rated” badges from sites you’ve never heard of.
Step 5: Put Vendors to the Test (Demos, Trials, and Reference Checks)
Now it’s time to get hands-on. Here’s how to do it without wasting hours:
- Demos: Don’t let vendors run the show. Give them your 2-3 use cases and ask them to show those in action. If they can’t, move on.
- Trials: Insist on a real trial or sandbox. Set it up with your own data (even if it’s just a sample). If it takes more than a day to get started, that’s a red flag.
- References: Ask for customers in your industry and size. Don’t just talk to the happy ones—ask what went wrong, what they wish they knew earlier.
Pro tip: Watch for over-promising. If a vendor’s answer to every question is “Yes, we can do that,” they’re probably stretching the truth.
Step 6: Look Out for Hidden Costs and Gotchas
The sticker price is rarely the full story. Watch for:
- User minimums: Some tools require you to pay for a certain number of seats, even if you don’t need them.
- Onboarding fees: Ask if setup or training costs extra.
- Integration headaches: Will you need a consultant just to hook it up to your CRM?
- Lock-in: What’s the contract length? Is there a real exit plan if things don’t work out?
What to ignore: “Value-based pricing” that’s impossible to decode. If it’s not clear what you’ll pay, walk away.
Step 7: Pilot With a Small Team (and Get Honest Feedback)
Don’t roll a tool out to the whole team right away. Pick a few reps (ideally, your skeptics and your power users). Have them use the tool for 2-4 weeks and track:
- Is it saving them time?
- Are they actually using it, or just clicking around?
- Does it create new problems (lost data, more admin work, etc.)?
Ask for blunt feedback. Ignore the vendor’s “adoption success” stats—trust your own people.
Pro tip: If your team is using workarounds or going back to old tools, that’s a sign the new tool isn’t solving the right problems.
Step 8: Make a Decision (and Set a 90-Day Review)
If the pilot goes well, roll it out—but keep it light. Don’t force adoption with threats; build buy-in by showing how it helps.
Set a 90-day check-in. Ask:
- Is the tool still solving the problems you bought it for?
- Are there new pain points you didn’t expect?
- Is the vendor still responsive, or did support disappear after the sale?
If it’s not working, don’t be afraid to pull the plug. Sunk costs are real, but so is the cost of a tool no one uses.
A Few Honest Takes from the Trenches
- No tool is a silver bullet. The best software just amplifies what’s already working.
- Most teams use only 20-30% of features. Focus on the basics, not the bells and whistles.
- Vendors oversell “AI” and “automation.” If it sounds too good to be true, it probably is.
- Adoption is everything. The fanciest tool is useless if your team hates it.
- Start simple, add as you grow. Don’t buy enterprise tools before you’re ready.
Keep It Simple and Iterate
Picking GTM software isn’t about chasing the latest trend or ticking every box on a feature list. It’s about solving real problems for your real team—right now. Start with your pain points, run real tests, ignore the hype, and don’t be afraid to change course if something’s not working.
Keep it simple, focus on what matters, and iterate as your team grows. You’ll save money, headaches, and a lot of “what were we thinking?” meetings down the road.