How to Choose the Right Sales Enablement Training Software

Eighty-one percent of organizations now conduct sales training online, reflecting a clear shift toward digital learning environments. But just moving training online doesn’t automatically make it effective. Too many companies still rely on outdated platforms, generic content, and clunky systems that overwhelm rather than empower.

Most sales reps are struggling because the tools meant to help them aren’t built for how they work. In a high-pressure, fast-paced sales world, it’s not enough to have training. So, how do you ensure you choose the right sales enablement training software?

Why Is It Important to First Understand Your Sales Team’s Unique Needs?

Choosing the right sales enablement training software doesn’t start with tech; it begins with people. That is why stepping back and understanding what your team needs to succeed is essential. 

It Ensures Training Targets Real Sales Team Needs

A study by CSO Insights found that 71% of companies take six months or longer to onboard new salespeople, and nearly one-third take over nine months. Even more striking, reps can take up to ten months to reach full productivity.

These numbers don’t just point to a slow ramp-up—they highlight a deeper issue: many companies are investing in training without a clear understanding of the actual skill gaps. Without identifying these gaps, it's impossible to create targeted, effective training that accelerates readiness and performance.

Too often, training is rolled out broadly and generically, assuming all reps need the same thing. But every team—and every rep—faces different challenges. For some, it’s mastering complex product knowledge, and for others, it's navigating buyer objections or adapting to new sales tools. The real problem isn’t always the lack of training—it’s the lack of relevant training based on actual, diagnosed needs.

Assess competency gaps instead of jumping straight to sales outcomes or pipeline stages. Ask diagnostic questions like:

• Which core selling skills are reps consistently underperforming in? (e.g., discovery, objection handling, closing)

• Are reps applying what they’ve learned in training during real conversations?

• What areas do frontline managers observe recurring weaknesses during call coaching or shadowing?

• Are new hires struggling with specific knowledge areas or skills despite completing onboarding modules?

• What feedback are reps giving about training usefulness and relevance?

By collecting feedback from reps, analyzing performance data, and incorporating manager insights, you can pinpoint where your training needs to be deeper and where it might need to change entirely.

It Shapes Training Around Roles, Locations, and Experience

The right training for a fully remote, global team will differ from that for an in-office group of SDRs. Understanding your team’s structure—who they are, where they work, and what experience they bring—is essential to designing effective enablement.

• New hires may need structured onboarding and foundational skill-building.

• Experienced reps benefit more from coaching, product refreshers, and advanced selling strategies.

• Remote or hybrid teams need asynchronous training that’s accessible, ideally embedded in the tools they already use, such as Slack, Teams, or SMS.

When mapping training formats and content to your team’s specific makeup, you ensure every rep gets what they need, when and how they need it.

It Aligns Rep Development With Real Business Outcomes

Understanding your sales team’s needs doesn’t stop with empathy—it’s a business strategy. When you know what your reps are working toward and where they struggle, you can align training with your company’s revenue goals.

For example:

• If the company is focused on upselling, training should center on uncovering latent customer needs and confidently presenting premium solutions.

• If the goal is to shorten the sales cycle, reps need help with qualification, objection handling, and closing techniques.
  
  

Training only delivers impact when it’s tied to outcomes. Without that connection, even the most engaging content risks becoming a box-checking exercise instead of a performance booster.

What Features Matter in Sales Enablement Training Software?

When choosing a sales enablement training software, it’s easy to get caught up in flashy features or the promise of "all-in-one" platforms. Today, the real value lies in tools that adapt to human needs, not just business metrics.

Aside from the fact that effective sales enablement tools matter, we should understand how they can empower our employees. Learn more from this blog: “How Sales Enablement Tools Empower Global Sales Teams?”

So, what features should we look for?

Content Personalization to Match Skill Levels and Roles

Not every rep is starting from the same place. New hires need foundational knowledge, while seasoned reps benefit from advanced strategies and nuanced coaching. 

Personalization helps each rep feel seen and equips them with the necessary tools. Great software should:

• Adapt to different experience levels (new reps vs. veterans)

• Offer AI-driven content recommendations

This is where platforms like Arist shine—delivering highly personalized, actionable training in the tools reps already use (Slack, Teams, SMS). 

Microlearning That Fits Reps’ Busy, On-the-Go Schedules

Salespeople don’t have time for hour-long modules or clunky eLearning portals. They need fast, focused lessons they can absorb during meetings or commute. 

Microlearning—short bursts of content delivered consistently—helps reps retain and apply knowledge in real time. It’s training that respects their schedule.

AI-Driven Recommendations That Evolve With Rep Performance

The smartest sales enablement tools learn with your team. AI can analyze patterns in rep performance and suggest training based on actual behavior, not assumptions. 

Are you struggling with closing? The platform surfaces content on closing strategies. Is there a new product launch? It pushes relevant messaging tips. It’s like having a personal coach in every rep’s pocket.

Seamless Integration With CRM and Communication Tools

Your software should sync with platforms your team already uses when learning is embedded into the workflow, and adoption skyrockets. Reps can get reminders, complete training, and track progress without toggling between systems.

Look for tools that:

• Seamlessly integrate with your CRM (like Salesforce)

• Fit into communication platforms like Slack or Teams

• Support easy login and user management

Real-Time Analytics to Monitor Progress and Close Gaps

If you can’t measure it, you can’t improve it. Real-time analytics help managers see what’s working, who’s engaging, and where support is needed. Progress tracking also gives reps ownership over their growth, helping them stay motivated and focused.

Make sure your software includes:

• Progress tracking for each rep

• Completion rates, quiz scores, and engagement data

• Manager dashboards to monitor learning impact

Mobile Access to Support Remote and Hybrid Selling Environments

With so many reps working remotely or in hybrid models, mobile access is no longer optional. Your training platform should work seamlessly across devices, allowing reps to learn from wherever they are—whether in the office, at home, or on the road.

Your sales enablement platform should be:

• Fully mobile-compatible

• Accessible via app, SMS, or browser

• Designed for learning in short bursts, from anywhere

Built-In Security and Compliance for Scalable Enterprise Use

Especially in industries with strict regulations, training must meet data security and compliance standards. Choose a platform that takes these needs seriously, offering encryption, user permissions, and compliance certifications. Peace of mind matters for leadership and the people using the tools.

How Do You Successfully Implement Sales Enablement Training Software?

Implementing new sales enablement software can feel like one more thing on your full plate — especially when your sales team juggles quotas, calls, and constant change. So instead of rushing through the rollout, take a step back. 

Here's how to implement your new sales enablement solution.

1. Start With the “Why” 

Your reps are already navigating a lot. So, before you roll out anything new, clarify the purpose: This isn’t another tracking tool. 

This is here to help you win. Frame it around outcomes they care about — faster onboarding, better call confidence, fewer lost deals.

2. Get the Right People on Board Early

Bring sales managers, enablement leads, and even frontline reps into the conversation from the start. When your team sees familiar faces championing the change, they’re more likely to lean in.

3. Make the Tool Work for Them

Customize the content to reflect what your reps face in the field — from real objections to updated product details. No one wants generic training. You can see if these are in your checklist when choosing your tools.

• Role-specific learning paths?

• Microlearning for on-the-go reps?

• Updated content that reflects your current market?

4. Test With a Small, Honest Team

Don’t start with your entire org. Choose a pilot group that’ll give you real feedback (not just the polite kind). What do they love? Where do they get stuck? Use that feedback to refine the rollout for everyone else.

5. Train and Support With Patience

People learn at different paces. Offer training in different formats—live sessions, quick videos, peer coaching—and don’t expect instant adoption.

6. Track Progress With Curiosity, Not Just KPIs

Look beyond numbers. Engagement and completion rates matter, but also listen. Are reps feeling more confident? Are managers noticing smoother calls?

Simplify Sales Training, Amplify Sales 

Sales teams today are stretched thin. But too often, the training designed to support them is outdated, hard to access, or disconnected from real-world sales challenges. That’s why the right training enablement tools matter now more than ever. 

With Arist, you can integrate training directly into the tools your team already uses—like Slack, Teams, or SMS—making it easier to access, absorb, and apply. Whether you’re supporting new hires or helping seasoned reps sharpen their skills, Arist helps you deliver impactful, bite-sized training right when and where it matters most.

Book a demo now!