If you’re running B2B sales, you know the sales process is more complicated than anyone wants to admit. Between onboarding new reps, keeping everyone on message, and getting ramp-ups down from “forever” to “soon-ish,” most teams end up drowning in tools and checklists. The right go-to-market (GTM) software can help—but only if you pick something that actually fits your workflow, instead of just adding more noise.
This guide is for sales leaders, enablement managers, and anyone sick of chasing their tail with one-size-fits-all “solutions.” We’ll dig into what really matters when choosing B2B GTM software for streamlining sales enablement and onboarding—and where tools like Wonderway actually deliver.
Step 1: Get Clear On What “Streamlining” Means for Your Team
Before you even look at software, get specific about what you’re trying to fix. “Streamlining” is vague. Are you:
- Onboarding new reps faster?
- Making sure everyone uses the same messaging and assets?
- Spotting who’s struggling before they burn out?
- Reducing manual busywork for your managers?
Pro tip: Write down the top three headaches your sales team deals with. If a tool doesn’t help with at least one, you probably don’t need it.
What to ignore: Feature lists that sound impressive but don’t address your pain points. “AI-powered coaching” doesn’t matter if your reps can’t find the latest pitch deck.
Step 2: Map Out Your Current Workflow (Warts and All)
You can’t fix what you don’t see. Grab a whiteboard (or shared doc) and map out how onboarding and enablement actually happen right now. Who does what? Where do things get stuck? Be brutally honest.
Here’s what usually crops up:
- Training’s scattered across Google Drive, email, and someone’s desktop.
- New reps shadow random calls and hope for the best.
- Managers spend half their time reminding people to finish onboarding modules.
- No one’s quite sure if the onboarding “works”—or how long it actually takes.
Why this matters: If you don’t know your bottlenecks, you’ll just add software on top of a broken process.
Step 3: Define Your Must-Haves and Nice-to-Haves
Once you know your real problems, make a two-column list:
Must-haves:
- Easy to set up and use (for both admins and reps)
- Centralizes training, playbooks, and assets in one place
- Tracks progress and highlights who’s struggling
- Integrates with your CRM (e.g., Salesforce, HubSpot)
- Decent reporting—so you know what’s working
Nice-to-haves:
- Built-in coaching or feedback tools
- Smart recommendations (but only if they’re actually useful)
- Mobile access
- Gamification (if your team isn’t too cool for it)
- AI bells and whistles (if they solve a real problem)
What to ignore:
- Overly complex customization—unless you have a full-time admin
- “All-in-one” claims that try to do everything but do nothing well
- Features that sound good in a demo but will never get used
Step 4: Shortlist and Demo Tools That Fit Your Reality
Now you’re ready to look at real options. Don’t get sucked into vendor hype. Focus on tools that:
- Match your must-haves (from Step 3)
- Are built for B2B sales, not generic “learning” or HR use
- Have real customer stories—not just testimonials from their friends
A few things to check during demos:
- How quickly can you add/update content? If it takes more than a few clicks, your assets will be out of date before your next hire starts.
- What’s the rep experience like? Clunky UI = low adoption.
- How does it help managers? If it just dumps more admin work on them, pass.
- What integrations are native? “Zapier-compatible” is fine, but native CRM sync saves headaches.
- What don’t they do? A good vendor will admit their limits.
Wonderway is one of the few tools built specifically for B2B sales enablement and onboarding. It centralizes training, connects to your CRM, and gives you clear visibility into who’s ramping and who’s stuck—all without a ton of setup. You can check out the details here.
Step 5: Run a Pilot (Don’t Buy Blind)
Never roll out new GTM software to your whole team on day one. Pick a small group—maybe one manager, a couple of reps, and someone from enablement. Have them use the tool for two weeks.
Track:
- How long does setup really take?
- Are people using it without you nagging them?
- Are training modules and playbooks actually easier to find and use?
- Can you spot struggling reps faster?
- Are managers spending less time chasing people?
If the answers are “yes,” you’re onto something. If not, cut your losses.
Warning: Don’t assume a tool will get better just because the vendor says a big update is “coming soon.” Buy what works today, not what might exist someday.
Step 6: Get Buy-In—and Keep It Simple
If the pilot goes well, bring in the rest of the team. But don’t just dump new software on them and hope for the best.
- Explain why you picked this tool (hint: it actually solves their real problems)
- Start with just the features you need—ignore the rest
- Collect feedback early and often (especially from the people who complain)
- Iterate: tweak your process as you go
Pro tip: Most failed software rollouts happen because teams tried to do too much at once. Nail the basics first.
What Works, What Doesn’t, and What to Watch Out For
What Works
- Tools that are easy for reps and managers to use (low friction = high adoption)
- Centralized, up-to-date content
- Clear reporting that tells you where onboarding breaks down
- Tight CRM integrations
What Doesn’t
- Over-engineered “learning platforms” that take months to implement
- Generic LMS tools built for HR, not sales
- AI features that offer “insights” but never actually help you close deals
- Anything that adds more work for frontline managers
Watch Out For
- Long onboarding periods (“It’ll be great in 6 months!”)
- Pricing that jumps up when you want key features
- Vendors who dodge hard questions about reporting or integrations
- Promises of “AI magic” without clear examples
Keep It Simple—And Iterate
Choosing the right B2B GTM software for sales enablement and onboarding isn’t about chasing the latest trends. It’s about fixing your real problems with the simplest tool that gets the job done. Focus on what your team actually needs, pilot before you buy, and don’t be afraid to tweak as you go. Sales is hard enough—your software shouldn’t make it harder.