So you’re leading a sales enablement team, and you keep hearing about platforms that promise to boost productivity, ramp up training, and make your GTM (go-to-market) process airtight. The pitches come at you fast—Smartwinnr, Highspot, Showpad, Mindtickle, and a dozen more. They all sound great on a slide deck. But how do you cut through the marketing fluff and figure out which one will actually help your sales team hit quota?
This guide is for anyone tasked with picking a sales enablement solution for a B2B team. Whether you're shopping for your first platform or looking to replace one that never really clicked, you'll want to keep things practical—no buzzwords, just what you actually need to know.
1. Get Clear on What You Actually Need
Before looking at features or reading reviews, get painfully honest about your current problems and must-haves. Way too many teams buy a tool and then end up using 10% of it. Don’t be that team.
Ask yourself:
- What’s broken? (Onboarding takes too long? Reps don’t use the latest pitch decks? Managers can’t see who’s struggling?)
- What do you need to fix right now, versus “nice to have someday”?
- Who’s going to use this—just sales, or marketing too? What about partners?
- Do you need to integrate with your CRM, LMS, or other tools—or is that overkill for now?
Pro tip: If you can’t write your core requirements on a single sticky note, you’re probably overcomplicating it.
2. Build a No-Nonsense Shortlist
You’re going to see lots of “feature matrices” and G2 Crowd badges. Ignore most of them. Instead, make a short list of platforms that might fit based on your needs. If you’re evaluating Smartwinnr, make sure it’s there, but don’t rule out options like Highspot, Showpad, Seismic, or even more focused tools.
How to build your shortlist:
- Google less, ask more. Talk to peers at similar companies. What do they actually use daily—and do they like it?
- Ignore the “biggest” platform hype. The biggest vendor isn’t always the best fit (or the most affordable).
- Check for real case studies. Look for specifics—“reps cut onboarding by 30%”—not vague claims.
- Filter out the kitchen-sink platforms if your team is small or just starting out.
3. Line Up Your Must-Have Features
This is where the sales pitches get thick. Every vendor will say they do “everything.” The truth? Most tools do a few things well and the rest just okay.
Typical features to consider:
- Content management: Can you actually find stuff, or is it a dumping ground?
- Training & microlearning: Is it easy for reps to consume and for you to update?
- Coaching & feedback: Can managers see who’s struggling and step in?
- Analytics: Are the reports useful, or just pretty graphs?
- Integrations: Does it actually connect to your CRM, chat, or calendar?
- Ease of use: Will reps (and managers) actually use it, or is it a chore?
What Smartwinnr does well: - Simple, quiz-based microlearning and knowledge reinforcement. - Gamification and contests—useful if your team likes a little competition. - Decent analytics on training engagement and results.
Where Smartwinnr (and others) can fall short: - Content management isn’t as robust as Highspot or Seismic. - If you want deep video coaching, Mindtickle or Lessonly might be stronger. - Integrations can be hit-or-miss. Ask for a demo of the specific connection you need.
Pro tip: Don’t get distracted by “AI-powered insights” unless you can see a real example of how it saves you time, not just a fancier dashboard.
4. Test Usability—Don’t Just Watch the Demo
Vendors love to show you a guided demo where everything works perfectly. The reality is, your reps are busy, impatient, and allergic to clunky software.
How to test usability:
- Insist on a sandbox account. Put 2-3 real users (a frontline rep, a manager, maybe someone from IT) in the tool for a week.
- Upload your own training or content. How long does it take? Where do you get stuck?
- Try it on mobile. Your team will probably use it on their phone in the field.
- Ask your crankiest user to try it. If they can’t figure it out, nobody will.
What usually goes wrong:
- “Easy to use” turns into five clicks to do anything.
- Search is slow or returns too much junk.
- Mobile experience is clunky or missing features.
Don’t skip this step. You’ll save yourself months of pain.
5. Dig Into Analytics—But Only What Matters
Every tool promises “data-driven insights.” But what can you actually measure—and does it matter?
Useful analytics:
- Who’s completed onboarding or new training?
- Which content gets used in real deals?
- Which reps need help, or aren’t engaging?
Smartwinnr’s analytics:
- Shows training completion, quiz scores, contest results.
- Decent for tracking engagement at a high level.
- Less granular on deal-specific content usage compared to tools like Highspot.
If you just need to know who’s learning and who’s not, Smartwinnr covers the basics. If you want to tie content usage directly to closed deals, you’ll want something more robust.
6. Check Integrations—and Don’t Take Their Word For It
“Integrates with Salesforce!” is on every vendor’s site. Reality: Sometimes it works, sometimes it’s a pain.
How to check:
- Ask for a live demo connecting to your actual CRM or chat tool.
- Ask how much IT involvement is needed—can a non-engineer set it up?
- What data flows both ways, and how often does it sync?
- If you use Microsoft Teams or Slack, test how notifications and training actually show up.
Red flags:
- “We’re working on that integration now.”
- “It’s available, but only on the enterprise tier.”
- “You’ll need to use Zapier/third-party connectors.”
If integrations are a dealbreaker, dig deep before you sign anything.
7. Budget Honestly—And Watch for Gotchas
Don’t just look at list price. Most platforms price per user, but extras add up: implementation fees, support, extra integrations, or analytics modules.
How to budget:
- Get a full quote for your actual team size and use case.
- Ask if pricing scales down as your team grows or shrinks.
- Check contract minimums—some vendors want year-long commitments.
- Ask about onboarding costs and support—are they included, or extra?
Where Smartwinnr typically lands:
- Mid-market pricing—less expensive than the biggest names, but not “cheap.”
- Generally includes core features, but check if advanced analytics or integrations cost extra.
- Implementation is straightforward, but don’t expect white-glove service unless you pay for it.
8. Reality-Check Support and Customer Success
You will need help. Maybe not now, but when things break or users get stuck, support quality matters.
How to check:
- Email or call support before you buy—how fast and helpful are they?
- Ask for references from customers in your industry or team size.
- Find out if you get a dedicated customer success person, or just a help desk.
What to ignore:
Shiny “NPS” or “customer satisfaction” numbers. What matters is how fast they help you when it counts.
9. Don’t Fall for the Shiny Object—Buy for Today, Not Tomorrow
It’s tempting to buy a tool because it promises to do everything you might need someday. That’s how you end up with shelfware.
- Prioritize solving your top 2-3 problems right now.
- If you outgrow the tool in a year, that’s fine—better than getting stuck with something bloated and expensive.
- Remember, no tool will magically fix a broken sales process.
10. Make Your Choice—Then Actually Use It
Once you pick a platform, keep it simple:
- Train your team on the basics—don’t try to use every feature out of the gate.
- Set a 30- and 90-day check-in to see what’s working (and what’s just noise).
- Kill off old tools or processes that overlap, so people don’t default to “the old way.”
Final thought:
Most sales enablement tools—including Smartwinnr—work best when you keep things focused. Solve the problem in front of you, measure honestly, and don’t be afraid to change course if your needs shift. You don’t win by picking the “best” platform on paper—you win by making something actually work for your team, today.