AI Sales Training & Coaching Tools That Make Learning Stick (2025 Edition)

You’ve just wrapped up a flawless sales-training rollout.
Reps loved it. Managers cheered. Enablement checked the box.
And then—within a week—half the team forgets what they learned.

You’re not alone. B2B reps forget up to 70 % of new knowledge within seven days (Gartner).
Traditional enablement wasn’t built for the speed of modern sales.

That’s why 2025 belongs to AI-guided training—platforms that deliver real-time coaching, contextual insights, and measurable skill growth.
At the center of this new movement is Proshort AI, the first platform to merge call intelligence, workflow integration, and behavioral scoring into a single “Skill Intelligence” system.

🔍 Sales Training vs Sales Coaching

Modern teams need both—and they need them where reps actually work.

🧠 How AI Transforms Sales Learning

1. AI Roleplays: Realistic buyer simulations to sharpen discovery and objection handling.

2. Real-Time Guidance: Context-aware prompts during live calls.

3. Post-Call Coaching: Automated feedback linked to real customer conversations.

4. Skill Scoring: Continuous measurement of key behaviors and progress.

5. Adaptive Learning: Personalized micro-lessons based on skill gaps and deal data.

⚙️ Quick Comparison

🥇 1) Proshort AI — AI-Guided Training & Coaching in the Flow of Work

Best for: Teams that want training that sticks—coaching and micro-learning delivered automatically where reps already work.

Unlike static LMS tools or conversation recorders, Proshort AI links every meeting, email, and deal update to measurable skill growth.
Its Skill Intelligence Dashboard maps real behaviors (discovery depth, objection handling, next-step clarity) to scores, then generates personalized coaching loops that appear inside Salesforce, Slack, or Gmail.

💡 How Proshort Works

• Before Calls: AI briefs surface stakeholder context, likely objections, and recommended discovery prompts.

• During Calls: Smart prompts flag missed signals (“budget mentioned – clarify timeline”).

• After Calls: Auto-summaries update CRM fields and trigger short training clips tied to the rep’s own conversation.

⭐ Standout Features

• Skill Intelligence Dashboard: Benchmarks behaviors across reps, deals, and time.

• Ask Anything: Query your sales data in natural language (“Which enterprise deals lack exec sponsor mentions?”).

• Deal Monitor: Identifies skill-linked risks (“pricing not discussed”) and launches micro-coaching.

• Playlists & Nudges: Shares best-practice clips and reinforcement alerts via Slack and CRM.

⚙️ Integrations

Salesforce • Slack • Gmail/Outlook • Zoom • Teams • Gong • Chorus • Google Workspace

💵 Pricing

Custom plans based on seats + features.

Why teams choose Proshort: It connects enablement → skills → revenue. Faster ramp, higher win rates, and zero training decay.

2) Gong — Conversation Intelligence for Coaching at Scale

Best for: Revenue ops leaders and sales managers seeking replicable top-performer behavior.

How it compares to Proshort:
While Proshort turns insights into action, Gong focuses on diagnosis—analyzing every call, email, and meeting to reveal what happened and why. It’s the industry’s reference for conversation intelligence, though it lacks Proshort’s in-workflow training and Skill Dashboard layer.

🔍 Highlights

• Captures and analyzes calls from Zoom, Teams, and CRMs.

• AI Smart Trackers flag pricing talks, competitor mentions, or objections.

• Robust deal forecast views for pipeline accuracy.

✅ Pros

• Easy search and clip sharing.

• Reliable transcription accuracy.

• Smooth Salesforce + Slack integration.

⚠️ Cons

• Setup and custom tracker tuning take time.

• No embedded training nudges.

Standout Feature: AI Smart Trackers detect key moments across languages and phrasing.
Pricing: Custom quote.

“Gong insights help us train reps and deliver better service to customers.” — Paul Santarelli, CSO @ PitchBook

3) Einstein Conversation Insights — Native Salesforce Coaching

Best for: Salesforce-first teams wanting AI coaching inside Sales Cloud.

How it compares to Proshort:
Proshort integrates across every system; Einstein lives entirely within Salesforce. It’s ideal for organizations deeply embedded in the Sales Cloud ecosystem who want call analysis without adding another platform.

🔍 Highlights

• Transcribes and analyzes calls in 36 languages.

• Flags keywords (competitors, pricing, product mentions).

• Embeds insights directly in opportunity records.

✅ Pros

• Seamless Salesforce UI integration.

• Daily “Call Insights Emails” for asynchronous coaching.

• Voice provider compatibility (Aircall, Dialpad, RingCentral).

⚠️ Cons

• Limited outside Salesforce.

• Overwhelming volume of insights without filters.

Standout Feature: Call Insights Email — auto-curated coaching digest for each rep.
Pricing: From $50 per user / month.

“ECI has been invaluable for digital coaching and reinforcing best practices across our hybrid sales team.” — Dain Rasmussen, SVP Sales, Inspirato

4) Chorus AI (ZoomInfo) — Conversation & Deal Intelligence

Best for: High-growth teams wanting deeper deal visibility and scalable coaching.

How it compares to Proshort:
Where Proshort connects skills to revenue impact, Chorus excels at pattern recognition across calls. It’s a powerful listening tool that feeds enablement programs but doesn’t yet deliver real-time guidance or Skill Scoring.

🔍 Highlights

• Records and analyzes Zoom/Teams meetings.

• Tracks talk ratios, objection types, and sentiment shifts.

• Ties conversation insights to pipeline momentum.

✅ Pros

• Flags risk themes and question frequency.

• Enriches data via ZoomInfo database.

• Allows clip sharing for peer learning.

⚠️ Cons

• UI feels dated.

• Transcription accuracy varies with accent.

Standout Feature: Deal Intelligence Dashboard links call patterns to pipeline health.
Pricing: Custom.

“Chorus brings customer conversations to life—we see exactly where to improve product and process.” — Michaela Bulling, Revenue Enablement, Hudl

5) Salesloft — Engagement + Coaching in One Platform

Best for: Teams seeking a unified platform for outreach, forecasting, and conversation intelligence.

How it compares to Proshort:
Salesloft offers broad sales-engagement automation, while Proshort specializes in skill growth and AI coaching. Pairing the two creates a powerful combo: Salesloft drives activity; Proshort improves execution quality.

🔍 Highlights

• AI summaries and meeting prep cheat-sheets.

• Real-time Buyer Signals from emails and site visits.

• Forecast accuracy boost via activity tracking.

✅ Pros

• Comprehensive toolset for AE teams.

• Strong CRM and email integrations.

• Manager playlists for scalable coaching.

⚠️ Cons

• Feature depth = steeper learning curve.

• May overlap with existing tools.

Standout Feature: Real-Time Buyer Signals prioritize high-intent prospects.
Pricing: Custom quote post-demo.

“[Salesloft] Conversations made training our remote team simple and actionable.” — Tyler Gibbons, Sr AE

6) Dialpad — Real-Time Coaching & Call Intelligence

Best for: Sales teams wanting live transcription, in-call prompts, and post-call summaries all in one platform.

How it compares to Proshort:
While Proshort’s coaching triggers are skill-based and contextual (e.g., “Discovery depth low—ask next-step question”), Dialpad focuses on real-time speech analytics. It’s excellent for live guidance but less focused on long-term skill intelligence.

🔍 Highlights

• Proprietary AI engine for live transcription and summarization.

• Real-time Assist Cards pop up with objection-handling tips.

• Unified workspace for voice, video, and messaging.

✅ Pros

• Very strong real-time accuracy.

• Generates automatic post-call summaries.

• Built-in call scoring and analytics.

⚠️ Cons

• Not specialized for sales training context.

• Interface can feel heavy for pure sales users.

• Support response times can vary.

Standout Feature: Real-Time Assist Cards — adaptive pop-ups suggesting talk tracks as the conversation unfolds.
Pricing: $15–$150 / user / month depending on tier.

“Dialpad’s impact has been substantial—we’re seeing clear improvements in customer interactions and operational efficiency.” — Josh Gilmore, VP CX, RE/MAX

7) Second Nature AI — Scalable Roleplays for Realistic Practice

Best for: Companies wanting lifelike AI roleplays without tying up managers.

How it compares to Proshort:
Second Nature pioneered AI roleplay, but Proshort goes further by connecting simulated practice with real-world performance data. Where Second Nature stops at scoring, Proshort keeps coaching reps after the call in live deals.

🔍 Highlights

• AI “Jenny” acts as a realistic buyer persona.

• Conversation scoring on tone, clarity, confidence.

• Dashboards for manager oversight.

✅ Pros

• Intuitive interface for roleplay setup.

• Strong feedback detail.

• Certifications and learning paths built-in.

⚠️ Cons

• Feels scripted versus dynamic customer language.

• Doesn’t analyze real calls for coaching continuity.

Standout Feature: Template Library with dozens of scenario types (discovery, objection, renewal).
Pricing: Custom.

“The AI feedback is detailed and actionable—great for practice before live calls.” — G2 Reviewer

8) Wonderway — Automated Call Scoring & Targeted Coaching

Best for: Enablement leaders needing continuous skill visibility.

How it compares to Proshort:
Wonderway grades calls; Proshort interprets them. Proshort’s Skill Intelligence layer explains why performance dropped and launches personalized learning nudges—turning analytics into guided improvement.

🔍 Highlights

• Auto-scores every call across criteria like talk ratio, question depth, next steps.

• Recommends specific training modules.

• Library of ready-made programs from top trainers.

✅ Pros

• Saves managers hours of manual review.

• Data-driven recommendations for each rep.

• Integrates with CRM and email tools.

⚠️ Cons

• Accuracy depends on available call data.

• Insights can feel generic without customization.

Standout Feature: Training Library curated by SaaS industry experts.
Pricing: Custom.

“Auto-scoring every call shows who follows the playbook and what separates our top performers.” — Kevin Gaither, ex-SVP Sales @ ZipRecruiter

9) Hyperbound — Roleplays + Real-Call Scoring + Hiring Assessments

Best for: Hyper-growth orgs needing scalable onboarding, coaching, and hiring insights.

How it compares to Proshort:
Hyperbound analyzes call data to create realistic practice, similar to Proshort’s simulation engine—but Proshort integrates these learnings directly into active deals and coaching dashboards, closing the loop between enablement and execution.

🔍 Highlights

• Roleplays in 25 + languages.

• Scores real and simulated calls with customizable rubrics.

• Identifies coachability and skill gaps pre-hire.

✅ Pros

• Excellent for multilingual teams.

• Detailed call analytics for managers.

• Integrates with Salesforce, Gong, and Google Meet.

⚠️ Cons

• Initial AI training setup required.

• May be overkill for smaller teams.

Standout Feature: AI-Powered Hiring Assessments — simulate sales scenarios for candidates.
Pricing: Custom.

“Instant feedback on every roleplay has been a game-changer for team performance.” — Brandon Bornancin, CEO, Seamless.ai

10) Quantified — Enterprise-Grade AI Roleplay & Coaching

Best for: Large enterprises wanting consistent, data-backed skill benchmarking.

How it compares to Proshort:
Quantified excels at deep-dive analytics on simulated calls. Proshort complements this by analyzing live customer interactions and updating each rep’s Skill Score automatically after every meeting.

🔍 Highlights

• Ultra-realistic AI buyers based on ICP profiles.

• Performance evaluation on confidence, clarity, empathy.

• Customizable scoring rubrics aligned to your methodology.

✅ Pros

• Scalable across global orgs.

• Robust reporting dashboards.

• Integrations with MS 365, Zoom, Salesforce.

⚠️ Cons

• Setup time for rubrics.

• Less focus on daily workflow integration.

Standout Feature: Customizable Rubrics for precise behavioral measurement.
Pricing: Custom enterprise plans.

“We use Quantified AI for coaching and onboarding—it’s flexible and powerful.” — G2 Reviewer

11) PitchMonster — AI Speech Coaching for Cold Calls & Demos

Best for: SDR and BDR teams refining pitch delivery.

How it compares to Proshort:
PitchMonster is perfect for practicing tone and clarity, whereas Proshort connects those behaviors to outcomes—showing how better delivery increases conversion and pipeline velocity.

🔍 Highlights

• Simulates cold calls and demos using uploaded scripts.

• Evaluates pacing, filler words, tone, and structure.

• Provides instant AI feedback with improvement tips.

✅ Pros

• Easy setup; great for self-coaching.

• Ideal for new-hire bootcamps.

• Built-in speech analytics.

⚠️ Cons

• Limited to practice environment.

• No link to real pipeline data.

Standout Feature: In-Built AI Speech Coaching — think “Grammarly for sales.”
Pricing: Custom.

“PitchMonster turns knowledge into repeatable action—fast.” — Ben Barton, Mentor Group

12) Momentum — Slack-Native AI Coaching & Workflow Automation

Best for: RevOps leaders combining AI coaching with real-time automation.

How it compares to Proshort:
Momentum streamlines RevOps workflows, while Proshort focuses on rep behavior and enablement. Used together, Momentum automates tasks and Proshort enhances how those tasks are executed.

🔍 Highlights

• AI-scored calls with threaded feedback.

• Slack deal rooms auto-update with insights.

• Workflow triggers push CRM updates automatically.

✅ Pros

• Tight Slack + Salesforce integration.

• Great for asynchronous coaching.

• Consolidates RevOps alerts.

⚠️ Cons

• Depends on clean CRM data.

• Geared toward Slack users.

Standout Feature: Workflow Automation — routes deal insights directly to the right channel in real time.
Pricing: $69–$99 / user / month.

“Every call is scraped by Momentum to pull insights that drive our business forward.” — Mark Turner, VP RevOps @ Demandbase

🧩 How to Make Sales Training Stick in 2025

Rolling out great content is only step one.
To create lasting behavioral change, teams must blend data, reinforcement, and personalization — exactly what Proshort was designed for.

1️⃣ Modularize Content

Break playbooks into bite-sized, searchable lessons.
Proshort’s Knowledge Graph automatically tags these modules by stage, persona, and skill so AI can recommend the right clip or snippet at the perfect time.

2️⃣ Learn in the Flow of Work

Reps don’t learn best in portals; they learn while selling.
Proshort surfaces micro-guidance directly inside Salesforce, Slack, Gmail, and call tools — no extra tabs, no friction.

3️⃣ Personalize Every Learning Path

Each rep has unique strengths.
The Skill Intelligence Dashboard maps gaps and dynamically adjusts micro-lessons so training remains relevant and high-impact.

4️⃣ Reinforce with Coaching & Recognition

Ongoing feedback builds confidence.
Managers can use AI-curated playlists from Proshort to celebrate top calls, highlight great objection handling, and recognize improvement publicly.

5️⃣ Measure What Matters

Traditional LMS metrics stop at “completed.”
Proshort links learning data to pipeline velocity, win rates, and forecast accuracy — turning enablement from a cost center into a revenue driver.

🥇 Proshort vs Other AI Sales Training Tools (2025 Comparison)