Coaching AI: How this virtual “teammate” upgrades sales training at scale

Tracy is a sales enablement manager. It’s Thursday, and she’s stuck in the office, staring at her calendar. It's packed with coaching sessions, but she knows her team of 50 reps needs more practice time than she can personally give them. Between reviewing pitches, providing feedback, and trying to standardize training across regions, she's stretched thin.

And she's not alone.

The reality: most sales and enablement managers can't give their teams enough coaching time. According to Gartner, the key to changing this lies in how we think about AI. When sales leaders treat AI as a teammate instead of just another piece of software, their teams close more deals and work more efficiently.

That's where AI coaching makes a difference. Instead of waiting for manager availability, sales reps can practice their pitches anytime. They can try new approaches without worrying about looking unprepared. And managers can focus their coaching time on what matters most — helping reps tackle complex sales challenges that require human expertise.

And based on LinkedIn's research, sales teams are ready and willing to level up — 82% believe AI-powered research will help them win more deals, and 84% are raising their hands for training on these tools. And they're right to be excited. The same research shows that 80% of reps who crush their quotas are already using AI in their sales process.

Let's look at how Coaching AI helps sales teams practice more, get better feedback, and build the confidence they need to win deals.

Why sales leaders struggle with coaching effectively and consistently

Here's a question that keeps sales leaders up at night: If coaching is so important, why isn't it working better?

Four major hurdles stand out:

• Your sellers aren't getting enough feedback (and they know it)
• Your managers are stretched too thin to personalize training
• The feedback that does happen? It's often subjective and hard to act on
• Practice makes perfect, but finding time to practice? Not so perfect

Because while 71% of sellers have dipped their toes into AI, most aren't swimming in the deep end yet and aren’t taking full advantage of AI for coaching. The cost of this gap? A whopping 41% of new deals get extended by 2-3 months, and worse — only 62% of those delayed deals ever make it to the finish line.

Let's break down each of these challenges and show you how AI coaching is flipping the script on traditional sales training.

Problem 1: Sellers aren't getting enough feedback on their skills

Your sales rep just finished pitch practice. They know they could have done better, but what specifically needs work? Without immediate feedback, they're left guessing. And by the time they get that feedback (if they get it at all), they've probably already used that same approach in front of a real customer.

This isn't just frustrating for reps — it's costing your company deals. When sellers can't get timely or objective input on their pitches, demos, and presentations, they repeat the same mistakes. Think about it: would you rather find out your demo needs work during practice, or after losing a six-figure opportunity?

The traditional fix? Schedule more coaching sessions. But that's like trying to fill a leaky bucket — there are only so many hours in a manager's day. Between their own targets, team meetings, and putting out fires, sales managers barely have time to give detailed feedback to every rep on every pitch.

How AI-powered coaching can help

Coaching AI eliminates the waiting game. With 24/7 access to feedback, reps can:

• Record multiple practice takes in a comfortable environment
• Get instant AI-generated scores and feedback on their delivery
• Receive actionable insights about their topic coverage, vocal clarity, and tone of voice
• Practice until they're confident, then submit their best take for manager review

The outcome? Managers can focus their coaching time on complex challenges while AI handles the fundamentals. And reps get the continuous feedback they need to improve — without the wait.

Problem 2: Managers lack time to personalize training

Your sales team just doubled in size. Great news, right? But now your managers are trying to coach 20 reps instead of 10, each with different strengths, weaknesses, and learning styles. One rep needs help with objection handling, another with demo delivery, and a third with pricing discussions.

The default solution? One-size-fits-all training sessions. But we all know how that goes — half the room is bored while the other half is struggling to keep up. It's like trying to teach swimming and advanced diving in the same class.

Meanwhile, your experienced reps want advanced coaching on complex deals, while your newer team members need fundamentals. Your managers end up splitting their limited time between both groups, which means nobody gets the focused attention they need.

Where coaching AI comes in

No more one-size-fits-all training. Coaching AI tailors the learning experience for each rep by:

• Analyzing each rep's performance data to identify specific skill gaps
• Providing customized feedback based on individual speaking patterns and presentation styles
• Allowing managers to set custom scoring criteria for different experience levels
• Letting reps practice at their own pace until they master each skill

For example, if a rep consistently struggles with technical product details, CoachingAI can focus their practice sessions on those areas while another rep works on improving their confidence and tone. It's like having a personal coach for every member of your team — without needing to clone your managers.

Problem 3: The feedback sellers get isn't objective or actionable

"Great job on that pitch!"

Nice to hear, but what made it great? What could make the next one even better? Without specific, measurable feedback, your reps are essentially throwing darts in the dark.

Even when managers try to give detailed feedback, it's inherently subjective. What one manager considers a confident tone, another might see as too aggressive. And honestly — feedback often comes down to general impressions rather than concrete data points your reps can actually use.

The result? Your sellers keep guessing. They might know something needs to change, but they're not sure exactly what or how to change it. It's like being told to "run faster" without a stopwatch to track your progress.

The coaching AI fix

Want feedback you can actually use? Coaching AI turns subjective opinions into measurable metrics:

• Topic coverage scores show exactly which key messages landed (and which didn't)
• Vocal delivery analysis breaks down clarity, pace, and tone of voice
• Detailed metrics track everything from filler words to speaking confidence
• Benchmarking against top performers shows reps clear targets to aim for

Think of it as having a professional sports coach with instant replay, performance analytics, and comparative stats — all focused on helping your reps win more deals. No more vague feedback or conflicting advice. Just clear, actionable insights that show exactly what to improve and how to improve it.

Problem 4: Sellers need more practice

"Practice makes perfect" sounds great in theory. But in reality? Your reps are practicing their pitches on real prospects because they don't have another option. It's like learning to fly a plane while carrying passengers — not ideal for anyone involved.

The traditional solution is roleplaying with managers or peers. But to be truthful, these sessions often feel awkward and inauthentic. Plus, scheduling conflicts mean they happen far less often than they should. When a rep needs to practice handling a specific objection, they can't put a customer on hold while they book a coaching session.

And even when role-play sessions do happen, the feedback loop is slow. Reps might only get one or two chances to practice before they're back in front of customers.

Practicing with CoachingAI 

Meet your team's new practice partner. CoachingAI, a feature of Bigtincan Readiness, lets reps:

• Get objective AI feedback on strengths and weaknesses so they get firm direction on how to improve
• Set up custom scenarios with specific personas, competitors, and objectives
• Run through pitches back-to-back until they nail every response
• Practice in a low-pressure environment where mistakes are learning opportunities, not lost deals

Your reps can practice handling turbulence (objections), try different flight paths (sales approaches), and perfect their landing (closing techniques) — all before they take real customers on board.

Even better, every practice session generates insights that help reps improve. No more wondering if they're ready for that big presentation — they'll know they are because they've already nailed it multiple times in practice.

Make AI your sales team's newest teammate

Bigtincan offers four AI tools that work together to help your sales team win more deals:

• GenieAI: Your always-on AI assistant that helps reps find answers and sales assets, research prospects, and get instant help during customer conversations
• CoachingAI: Your virtual coach that provides objective feedback on pitches, demos, and presentations
• RolePlayAI: Your practice partner for perfecting sales conversations through realistic simulations
• MeetingsAI: Your conversation intelligence tool for AI-generated meeting summaries, automatic CRM note logging, and catalog of sales calls for verifying reps are putting coaching into practice

Here's how to put these tools to work:

Start with what matters most

• Begin with your most common sales scenarios — the ones your team faces daily
• Focus first on core skills like pitch delivery and objection handling
• Set up standard scoring criteria that align with your sales methodology

Make AI part of daily work

• Use GenieAI to answer product questions and research prospects
• Schedule weekly RolePlayAI sessions for practicing common objections
• Review CoachingAI feedback after each customer presentation

Help managers coach better

• Use CoachingAI scores to spot which reps need help with specific skills
• Have managers use GenieAI to identify knowledge gaps across the team
• Track RolePlayAI data to see which scenarios challenge reps most often
• Review scores of sales calls in MeetingsAI to see how, if, and where coaching is paying off

Remember: AI coaching doesn’t replace human coaches — it makes them more effective. When managers and AI work as teammates, your reps get the best of both worlds: consistent practice and expert guidance when they need it most.

Use Coaching AI to make training, learning, and onboarding more effective at scale

The future of sales coaching isn't about choosing between AI and human coaches — it's about bringing them together to create something better than either could achieve alone. When you position AI as a teammate rather than just another tool, you unlock new possibilities for your entire sales organization.

Think about it. What if every rep on your team could:

• Practice whenever they need to, not just when a manager is available
• Get instant, objective feedback on every pitch
• Learn at their own pace without falling behind
• Build confidence before getting in front of customers

That's not just a nice-to-have — it's a competitive advantage in today's market. And with tools like CoachingAI and RolePlayAI, it's not just possible — it's practical.

Ready to see how AI can transform your sales coaching? Get a demo of Bigtincan's AI-powered coaching solutions and discover why forward-thinking sales organizations make AI their newest teammate.