If you’re drowning in sales tech options and every vendor promises to “transform your pipeline,” you’re not alone. Choosing the right B2B go-to-market (GTM) software can feel like trying to pick the right cable in a nest of wires—there’s a lot of noise and it’s hard to know what actually works. This guide is for sales leaders, ops people, and anyone who’s tired of bloated tools that don’t deliver. We’ll walk through how to actually choose B2B GTM software that streamlines your sales process—and we’ll use Clientpoint as a real-world example.
1. Get Clear on What You Actually Need
Before you get dazzled by sales demos, figure out your real needs. Most teams don’t need 100 features—they need a few things that work well.
Ask yourself: - Where are deals stalling or falling off? - What repetitive tasks slow your team down? - What’s the biggest pain your sales reps complain about? - Are you losing deals because of poor follow-up, messy proposals, or bad handoffs?
Pro tip: Write these answers down. If a tool can’t solve your top 2-3 problems, it’s not the right fit—no matter how shiny the dashboard looks.
2. Map Out Your Sales Process—For Real
Don’t just grab generic process maps from Google. Sketch out (even on paper) how deals move from lead to close at your company. Where do people get stuck? What do reps have to do manually? Where do things get lost?
Look for: - Proposal creation and delivery bottlenecks - Disjointed communication with prospects - Manual follow-ups or reminders - Handoffs between sales, legal, and customer success
When you know exactly where your process hits friction, you can look for software that actually fixes those kinks, not just adds another layer.
3. Make a Shortlist: What Really Matters in GTM Software
Ignore the buzzwords. Here’s what you actually want in B2B GTM software:
- Ease of use: If it takes a week of training, your reps won’t use it. Period.
- Proposal and document management: Can you build, send, and track proposals in one place?
- Automation: Does it handle reminders, follow-ups, and document updates so reps don’t have to babysit deals?
- Integration: Does it play nice with your CRM, email, and calendar?
- Analytics that matter: Can you see who opened your proposal, when, and for how long—or is it just vanity metrics?
- Collaboration: Can legal, sales, and customer success actually work together in the tool, or are you back to email chains?
What to ignore: - AI “deal scoring” that’s just a random number - Fancy dashboards you’ll never look at - Overcomplicated workflow builders that need their own admin
Some products, like Clientpoint, focus on making proposal creation, delivery, and tracking dead simple, with just enough automation to cut the busywork.
4. Demo Like a Skeptic
The demo is where most teams get hypnotized. Don’t be that team.
How to run a useful demo: - Bring your own real-world use case (your actual sales doc or process). - Ask the rep to show your workflow, not their canned example. - Have a frontline rep—not just a manager—click through the tool. - Ask, “How many clicks to send a proposal? What happens if there’s a change? How does the client respond?”
Red flags: - They can’t show your use case without “getting back to you.” - Features look good in the demo but require custom setup (read: hidden services fees). - Everything looks great until you ask, “Who actually uses this daily?”
Pro tip: Get the trial and try it on a real deal, even if it’s just a test. If it’s more work than your current system, walk away.
5. Talk to Real Customers (Not Just Reference Calls)
Customer stories on vendor websites are cherry-picked. Ask to talk to a customer who actually switched from a competitor, or who’s not in the vendor’s core vertical.
What to ask: - What did you stop using after adopting this tool? - Where does it break down or annoy your team? - Is there something you wish you’d known before buying? - How’s support—do they actually respond, or is there a “support portal” black hole?
If you hear a lot of “well, we’re still working on that feature…” that’s a sign the product is still baking.
6. Check the Integration and Migration Reality
Most B2B sales teams already have a CRM, email, and a graveyard of old tools. Any new software should fit in without a months-long IT project.
Checklist: - Does it connect easily to your CRM (Salesforce, HubSpot, etc.)? Or does it need a third-party connector? - Can you pull in your existing templates, client data, and contacts? - If you leave, can you get your data out? Or are you locked in forever? - How long does a typical implementation take? (Weeks, not months, is good.)
Clientpoint, for example, offers pre-built integrations with common CRMs and makes it easy to pull in existing proposal templates. You shouldn’t have to rebuild everything from scratch.
7. Pilot With a Skeptical Eye
No matter how slick the sales pitch, the rubber meets the road in a real pilot.
How to run a pilot: - Pick one or two sales reps (ideally, one tech-savvy, one not). - Run your actual sales process for 2-3 deals. - Measure: Did it save time? Did proposals go out faster? Did clients respond quicker? - Ask your team: What do you hate about it? What do you actually like?
If the tool genuinely makes life easier, you’ll know fast. If it’s just “interesting” but nobody bothers, don’t force it.
8. Don’t Overthink Pricing (But Don’t Get Suckered)
Most GTM tools charge per user or per proposal. Watch for: - Hidden implementation or “success” fees - Minimum seat requirements - Extra charges for integrations or support
What matters: Paying a bit more for something your team actually uses is better than saving $20/user/month on shelfware.
If pricing isn’t clear or the sales rep dances around the answer, that’s a bad sign.
9. Focus on Adoption, Not Features
Fancy features don’t matter if nobody uses them. The best B2B GTM software is the one your team will actually adopt.
Tips for driving adoption: - Keep the first rollout simple: one process, one template, one team. - Get feedback fast—what’s working, what isn’t. - Tweak as you go. Don’t try to automate everything on day one.
What Actually Matters
It’s tempting to chase the “next big thing” in sales tech. But most teams just need a tool that helps them send better proposals, track responses, and close deals without extra hassle. Whether you’re looking at Clientpoint or any other platform, focus on your real sales bottlenecks, ignore the hype, and pick something your reps will actually use.
Start small, keep it simple, and tweak as you go. The best B2B GTM software is the one that quietly gets out of your way—so your sales team can get back to selling.