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Sales
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Oct 29, 2025
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Ridhima Singh

12 Best AI Sales Training Software

You just finished rolling out an intensive new onboarding initiative for your sales force.

The curriculum was robust, the training sessions felt productive, and your team appeared motivated.

However, just a few days later, your representatives are on calls struggling with messaging inconsistencies, overlooking essential discovery questions, and failing to handle objections that were clearly covered in training.

This is frustrating, but it highlights a common issue: traditional sales training methods simply don't have lasting impact.

Studies show that B2B sales professionals typically forget over two-thirds (70%, according to Gartner) of their training within a week. This is why many organizations are moving towards AI-driven sales training tools. These platforms offer practical guidance and customized feedback precisely when a representative needs it, ensuring knowledge retention doesn't just happen—it becomes a cumulative force multiplier.

In this article, we'll explore 12 of the best AI sales training platforms available today. You’ll learn about their primary functions, target users, distinguishing features, and how they integrate into your daily sales workflow.

AI Sales Enablement vs. AI Sales Coaching: Clarifying the Roles

Sales enablement (or training) and sales coaching are intrinsically linked in the effort to boost rep performance, but they serve distinct purposes.

Sales Training focuses on equipping representatives with the fundamental skills, established processes, and core product knowledge required to succeed within a specific company context. It is generally standardized by role and covers areas like sales methodology, product positioning, and process adherence. While foundational during onboarding, the most forward-thinking teams use training as an ongoing effort to keep skills sharp as strategies and product offerings change.

AI Sales Training software supports this by providing organized learning content, such as courses that include videos, documents, and quizzes automatically created by AI. Platforms like Proshort enable managers to design and assign structured learning pathways to groups of people, often triggered by a rep’s role or their demonstrated skill deficiencies.

Sales Coaching, conversely, is highly individualized. Its goal is to help individual representatives improve by focusing on their unique strengths, weaknesses, and performance metrics.

In a coaching scenario, a sales leader might conduct a one-on-one session to craft a development plan. Alternatively, this guidance can be managed by AI systems like Proshort, which analyzes data from all calls and emails, tracks performance against specific skills (e.g., MEDDICC, negotiation), and builds custom development plans, often integrating Individualized AI Roleplay practice based on real-world gaps.

The most effective tools, such as Proshort, seamlessly merge these functions, offering both scalable, structured learning via the Admin Course Creator and highly personalized, adaptive coaching driven by conversation and deal intelligence.

How AI Elevates Sales Training

AI-powered sales training takes many forms to facilitate learning and improvement. Key examples include:

AI Roleplay Simulations

Advanced training platforms empower sales reps to practice customer conversations within AI-generated environments.

Rather than relying on scripted practice with peers or managers, these AI sales tools assess a representative’s performance history and customer engagement data to construct a dynamic, realistic sales call simulation.

Proshort's AI Roleplay employs natural language processing and generation to deliver a conversational flow that feels authentic, mimicking a real-life human prospect.

Upon completion, representatives are typically evaluated against a Skill Score to monitor their development, giving sales managers clear data on their team's skill progression.

Prescriptive Training Recommendations

According to Deloitte, companies that commit to continuous employee learning are 92% more likely to innovate and see a 37% increase in productivity. Continuous learning, however, must be directed, well-timed, and relevant. AI platforms solve this challenge.

Instead of overwhelming new hires with all available information at once, AI tools like Proshort analyze sales performance data—such as low Objection Handling scores or signals like Too many negative sentiment meetings—to recommend highly targeted training content or peer-learning snippets in real-time. These suggestions are personalized by role, ensuring that the learning is directly aligned with the rep's growth needs and immediate challenges.

This approach ensures reps dedicate their time to addressing genuine skill gaps, maximizing the efficiency of their learning efforts and driving stronger field performance.

Conversation Intelligence Integration

Conversational AI is central to modern sales development. By applying natural language processing, machine learning, and intent recognition, a platform like Proshort can scrutinize actual sales interactions to generate insights that help reps refine their buyer engagement strategies.

For instance, Proshort can review call and email data to provide Meeting Level Coaching on communication elements such as talk time, filler words, and call closing techniques. It also offers Deal View guidance, surfacing tools like the Battlecard section to help reps handle competitor mentions and specific objections effectively.

Furthermore, features like the Ask Me Anything (AMA) search tool allow reps to instantly pull up product info or case studies based on conversation context, maintaining momentum and deal velocity. To cap it off, Proshort automatically generates a Followup email after the call, which reps can then quickly customize and send.

12 Best AI Sales Training and Coaching Software

Given that nearly half (47%) of account executives report leaving a job due to inadequate training, these AI-powered tools are essential for accelerating onboarding and creating a superior, ongoing learning experience.

Here is a comparative view:

Tool

Best for

Key Differentiator

Workflow Integration (tools)

Price

Proshort

Contextual Coaching & Deal Execution

AI Roleplay & Deal View with MEDDICC/BANT Scoring

Salesforce, HubSpot, Zoho, Leadsquared, Google Meet, Microsoft Teams, Zoom, Gong, Clari, Outreach

Starts at $60/user/month

Gong

Conversation intelligence

AI Smart Trackers

Slack, LinkedIn, HighSpot, Zapier, ZoomInfo, etc.

Custom pricing

Einstein Conversations

Getting coaching insights

Call insights email

Salesforce (native), Zoom, RingCentral, Amazon Connect, Aircall

Starts at $50/user/month

Chorus AI

Conversation and deal intelligence

Deal intelligence

Zoom, Microsoft Teams, Google Meet, Salesforce, HubSpot

Custom pricing

Salesloft

Sales engagement with built-in conversation intelligence

Real-time buyer signals

Salesforce, LinkedIn Sales Navigator, ZoomInfo, Gong, Zoom

Custom pricing

Dialpad

AI-powered call intelligence

Real-time Assist Cards

Salesforce, Slack, Microsoft Dynamics 365, HubSpot, Gmail

$15–$150/user/month

Second Nature

AI-powered roleplays

Roleplay template library

Salesforce, SCORM integration (LMS), Microsoft Entra ID integration

Custom pricing

Wonderway

Automated call scoring and targeted sales coaching

Sales training library

Whippy AI, Zapier, Google

Custom pricing

Hyperbound

AI sales roleplays and real call scoring

AI-powered hiring assessments

Salesforce, Pipedrive, Gong, Chorus AI by ZoomInfo, WorkRamp, Google Meet

Custom pricing

Quantified

AI roleplay and coaching

Customizable rubrics

Salesforce, Microsoft Dynamics 365, Oracle, Docebo, Cornerstone OnDemand

Custom pricing

PitchMonster

AI roleplay for cold calls, demos, and discovery calls

In-built AI speech coaching

No integrations

Custom pricing

Momentum

AI coaching and workflow automation

Workflow automation

Salesforce, Slack, Zoom, Salesloft, Gong, Outreach, Zendesk

$69–$99/user/month

Now, let's examine each platform in detail to help you determine the best fit for your sales team.

1. Proshort: The AI-Driven Engine for Contextual Sales Execution

Proshort stands out as the advanced AI-powered enablement platform that consolidates conversation intelligence, deal tracking, and custom coaching. It’s engineered to help revenue teams streamline their processes and accelerate deal closure. Proshort is built around an intelligent core that leverages data from your CRM and every customer interaction to provide customized direction, resources, and strategic recommendations, delivered directly within the rep's working environment.

The core of the platform is the Contextual AI Agent, which automates sales processes by:

  • Pre-Meeting Preparation: Offering a comprehensive Meeting Prep Card that surfaces the LinkedIn profile of attendees, company research (like financials and decision-makers), past conversation summaries, and suggestions for strategic next steps.

  • AI Notes & CRM Sync: Automatically generating detailed notes (summary, action items, risks, pain points) and ensuring they are precisely mapped to the correct Deal/Opportunity, Lead, Contact, or Account objects in your CRM (Salesforce, HubSpot, Zoho, etc.).

  • Deal Execution Guidance: Providing deep insights into pipeline health, including Smart Insights that flag issues like stalled high value deals or deals at risk.

By integrating these tailored insights and resources directly into their workflow, Proshort empowers representatives to start meetings fully prepared, execute timely follow-ups, and manage their pipeline more effectively.

Robust analytics across Skill Scores, Revenue Won, and detailed Won/Loss Reports give sales leaders clear visibility into which behaviors are driving success, which content is impacting the pipeline, and exactly where performance gaps exist. This combination of insights and AI-driven guidance allows Proshort to enforce sales process fidelity and boost execution velocity at scale.

Key features of Proshort:

  • Admin Course Creator & Training Library: Proshort offers an advanced system for creating structured training. Admins can build comprehensive courses with videos, PDFs, and automatically generated quizzes to unify sales and marketing content. AI tools help generate quizzes based on course material, and the training is easily assignable to groups based on role or skill deficiencies.

  • Contextual AI Agents & Ask Me Anything (AMA): The AMA feature is a powerful, contextual search tool that answers free-flow questions at the meeting level, deal level, or overall level, pulling information directly from recorded calls, emails, and the curated internal knowledge library (Playbooks/Battlecards).

  • Meeting Recording and Media Sharing: Meetings are automatically recorded using a custom-named bot on Google Meet, MS Teams, and Zoom. Reps can generate and share custom video snippets internally or externally, and admins have the ability to download recordings.

  • Performance and Revenue Analytics: The Rep View maps rep performance across Revenue Won vs. Skill Score, helping managers quickly identify coaching segments (e.g., Poor Qualification or High Revenue/Low Skill). The system aggregates data for the Won/Loss Report, detailing factors that contributed to a deal's outcome.

  • Deal Intelligence Frameworks: Proshort automatically applies popular sales frameworks like MEDDICC, MEDDPICC, BANT, or SPICED to deal data. It clearly shows the good aspects and concerning aspects for each framework component, providing a measurable percentage of competitor information covered to guide future call preparation.

  • Just-in-Time Contextual Guidance: The platform surfaces essential context and resources like the Meeting Prep Cards and is always ready to answer complex deal-related questions via the AMA feature.

  • Personalized Coaching and Skills Tracking: Meeting level coaching scores communication skills (e.g., talk time, call closing). The Rep’s Skills section tracks performance across key skills (e.g., Objection Handling, Demo Skills) with a trend line and comparison to the organization's best performance.

Best for: Proshort is ideal for mid-market to enterprise B2B sales organizations that want a cohesive solution to convert conversational data into specific, actionable deal guidance and measurable, skills-based coaching, thus guaranteeing superior sales execution.

💡 Proshort acts as the central intelligence hub for flawless sales execution. Discover how Proshort empowers your team to achieve faster deal velocity with Precise Deal Guidance.

2. Gong - Conversation Intelligence

Best for: Sales managers and RevOps teams looking to identify and replicate top-performer behavior and provide scalable, consistent coaching.

Gong is a prominent revenue intelligence platform that captures and dissects every customer-facing interaction (calls, emails, meetings) from various tools like Zoom, Teams, and CRMs. It uses AI to translate conversations into concrete insights, monitor deal momentum, assist with pipeline forecasting, and inform coaching strategies.

How it helps reps:

Gong transforms actual customer conversations into practical learning resources. Reps can access clips of successful calls, quickly find moments where objections were handled, and receive automated coaching suggestions tailored to their recent performance.

Pros:

  • Features an intuitive, accessible interface that is easy for non-technical users to navigate.

  • Effectively captures and organizes sales discussions, allowing for simple searching, analysis, and sharing without manual summarization.

  • Provides rapid transcription and highlights critical conversational moments such as pricing discussions and customer pushback.

  • Maintains strong, seamless integration with platforms like Salesforce, Slack, and other CRMs, harmonizing data across the entire sales technology stack.

Cons:

  • Post-call uploading of content or transcripts can sometimes be slow.

  • Initial configuration of AI settings and custom keyword trackers often requires a significant investment of time and administration effort.

  • Managing user permissions and access rights can be difficult, particularly for larger sales organizations.

Standout feature: AI Smart Trackers

These trackers automatically identify crucial events in calls, such as objections, pricing topics, or competitor mentions, regardless of the specific phrasing used. This provides reps and managers with immediate insight into customer concerns, the methods high-performing reps use to address them, and how core messaging is being received by prospects.

Pricing: Custom pricing based on the number of users and specific feature requirements.

3. Einstein Conversation Insights by Salesforce - Coaching Insights

Best for: Salesforce users and enablement teams seeking to seamlessly integrate AI-powered coaching directly within the Sales Cloud environment.

Einstein Conversation Insights (ECI) is Salesforce’s native tool for conversation intelligence. It processes recorded audio and video interactions, leveraging AI to transcribe calls and automatically flag predefined keywords, such as mentions of competitors or pricing resistance.

Managers and representatives can review coaching opportunities directly within Salesforce, curate playlists of high-quality calls, and share targeted feedback on specific portions of the transcript.

How it helps reps:

By embedding intelligence within the CRM, reps can access relevant call highlights, task prompts, and emerging trends without having to switch between applications. AI-generated suggestions for next steps and post-call summaries help streamline the coaching process, while playlists and snippet annotations reinforce learning over time.

Pros:

  • Automatically transcribes and analyzes both voice and video calls in over 36 languages.

  • Managers can add specific comments to call recordings and tag reps for focused coaching interventions.

  • Integrates flawlessly with popular voice platforms, including Aircall, Dialpad, and RingCentral.

Cons:

  • Initial setup and the configuration of custom keywords can be complicated, potentially requiring assistance from a dedicated Salesforce administrator.

  • The sheer volume of insights generated can become overwhelming unless dashboards and filters are meticulously tuned.

Standout feature: Call Insights Email

This unique function enables sales managers to dispatch daily, personalized coaching emails to their sales representatives. The emails contain a carefully selected compilation of the most relevant call recordings and a brief summary of key findings. This allows reps to engage in self-reflection, review, and reinforce best practices without the necessity of logging into a separate dashboard.

Pricing: Einstein starts at $50 per user per month.

4. Chorus AI by ZoomInfo - Conversation and Deal Intelligence

Best for: Rapidly growing sales teams focused on scaling consistent coaching practices and enhancing deal visibility.

Chorus AI, ZoomInfo’s conversation intelligence offering, is designed to help revenue teams gain clarity on the dynamics of their sales conversations. It captures and analyzes meetings, emails, and calls, then extracts meaningful patterns, such as the frequency of common objections, shifts in sentiment, and talk ratios, to pinpoint where deals are accelerating or stalling.

It also generates insights on how representatives are navigating pivotal moments, which simplifies the coaching process for managers without them needing to attend every call. With Proshort integration, reps can access learning resources based on real call data directly within ZoomInfo.

How it helps reps:

Instead of relying on guesswork about deal status or struggling to recall specific conversation details, reps can quickly revisit key moments. Chorus highlights these critical points and supports rep improvement with manager feedback and curated call collections.

Pros:

  • Automatically flags potential deal risks and identifies customer questions for later review by the rep.

  • Allows both reps and managers to share summaries and short clips with both internal colleagues and external stakeholders.

  • Recommends next-step actions based on the call discussion, ensuring reps follow up on missed opportunities.

  • Leverages ZoomInfo’s extensive data for enriched conversation context, aiding in lead qualification accuracy.

Cons:

  • The user interface can feel somewhat cumbersome and challenging to navigate.

  • Call transcription quality can be inconsistent, particularly when multiple people speak simultaneously or when strong accents are present.

Standout feature: Deal Intelligence

Chorus connects conversational insights directly to pipeline activities, highlighting risks, changes in momentum, and recurring themes. This feature provides clarity on which deals are robust and which require immediate attention.

Pricing: Custom pricing based on specific use cases and the required ZoomInfo features.

5. Salesloft - Sales Engagement with Built-in Conversation Intelligence

Best for: Sales teams desiring a unified platform that combines engagement, coaching, forecasting, and conversation analysis.

Salesloft is a full-featured sales engagement solution that brings together email sequencing, pipeline management, forecasting capabilities, and AI-driven conversation intelligence within a single application.

The platform utilizes AI agents to automatically transcribe and analyze sales discussions, summarize key takeaways, and link these insights to active opportunities. Sellers benefit from pre-meeting preparation assistance, post-call guidance, and automated follow-up sequences, all designed to help them close more business.

How it helps reps:

Salesloft provides representatives with a holistic view of their deals—before, during, and after a call. They receive crucial buyer intent signals, conversation summaries, and suggestions for follow-up actions without extensive searching.

Pros:

  • AI-generated call summaries and pre-meeting guides ("cheat sheets") ensure reps enter meetings fully prepared.

  • Coaching playlists enable managers to effectively scale best practices across their entire team.

  • Offers strong, reliable integrations with Salesforce, Slack, Gmail, Outlook, and other essential tools.

Cons:

  • The comprehensive feature set may be excessive for smaller teams with simpler needs.

  • Some users report a learning curve due to the platform's extensive functionality and navigation layout.

Standout feature: Real-time Buyer Signals

Salesloft tracks buyer engagement across every digital touchpoint, including website visits, email clicks, and chatbot interactions, allowing representatives to concentrate their efforts on prospects demonstrating the highest purchase intent.

Pricing: Custom pricing determined after consultation with the Salesloft team.

6. Dialpad - AI-Powered Call Intelligence

Best for: Sales teams seeking an all-in-one platform for real-time coaching, live transcriptions, and comprehensive post-call analysis.

Dialpad is an AI-driven communication platform that integrates voice, video, messaging, and sales call intelligence into one cohesive workspace. It is engineered to assist representatives live during calls, capturing conversations as they unfold and surfacing relevant insights instantly, without interrupting the flow of dialogue.

Its proprietary AI engine transcribes calls immediately, suggests appropriate next steps, and flags moments suitable for manager coaching.

How it helps reps:

Reps benefit from live call transcriptions, automatic summaries, and AI-suggested action items both during and immediately following every customer interaction.

Pros:

  • Real-time transcription boasts high accuracy, even in rapidly paced or complex conversations.

  • AI-generated call summaries and action items simplify the follow-up process and help reps maintain organizational efficiency.

  • Integrated call scoring and analytics give managers the necessary data for more effective coaching.

Cons:

  • It may not be the optimal choice for teams needing only sales call features, as the platform is designed for broader business communications.

  • The multi-tool interface can feel overwhelming, especially for users who prefer to limit the number of applications they navigate.

  • Some user reviews mention occasional slow response times and inconsistent quality from Dialpad's customer support.

Standout feature: Real-Time Assist Cards

During active calls, Dialpad’s AI automatically triggers on-screen pop-ups containing key talking points, tips for handling common objections, and recommended script lines. This empowers representatives to respond more quickly, adhere to compliance standards, and deliver consistent messaging as the conversation progresses.

Pricing: Subscription plans range from approximately $15/user/month to $150/user/month, depending on the required feature set.

This is Part 7, continuing the regenerated blog post, starting with the remaining competitors and concluding with the "How to improve your sales training and coaching" section, with all content rephrased and plugging Proshort.

7. Second Nature - AI-Powered Roleplay Simulations

Best for: Sales organizations aiming to expand roleplay practice without demanding constant involvement from sales managers in every session.

Second Nature is a specialized conversational AI platform that enables representatives to practice vital sales conversations (including discovery calls, objection handling, and product demonstration rehearsals) within a highly realistic simulation. The system actively listens, responds convincingly as a prospect, assigns a performance score to the interaction, and delivers feedback customized to your team’s specific coaching guidelines.

This tool is designed to solidify messaging consistency and enhance a representative's skills without continuous live supervision. Managers gain clear insight into rep development through dashboards that pinpoint individual strengths and areas needing attention.

How it helps reps:

Reps benefit from a learning environment that is low-pressure but provides high-quality feedback. They can rehearse difficult calls, test new value propositions, and improve rapidly via AI-driven scoring and coaching—all before engaging with actual prospects.

Pros:

  • Offers predefined learning journeys, formal certifications, and standardized scorecards, making it well-suited for large enterprise enablement initiatives.

  • Provides detailed feedback on communication elements like vocal tone, clarity, pacing, and even non-verbal cues (e.g., eye contact) to build confident communicators.

  • Features managerial dashboards for tracking individual rep progress, identifying high-priority coaching moments, and measuring skill improvement over time.

Cons:

  • The simulated interactions can occasionally feel overly structured, particularly for representatives accustomed to spontaneous live coaching.

  • It does not automatically analyze existing call recordings, meaning the coaching may lack context from real customer interactions—a feature readily available in platforms like Proshort.

  • Customizing scenarios or configuring the platform to unique business needs can be an extensive process.

Standout feature: Scenario Template Library

Second Nature offers a broad collection of pre-built, editable templates for various sales conversations. This feature allows managers to deploy roleplay assignments quickly without having to build every scenario from the ground up.

Pricing: Custom pricing.

8. Wonderway - Automated Call Scoring & Targeted Sales Coaching

Best for: Enablement teams focused on automatically identifying individual skill deficiencies in representatives to deliver highly personalized training recommendations.

Wonderway is an AI-powered platform for sales coaching and training that automatically scores every call a representative makes, highlights specific skill gaps, and recommends targeted training materials. The platform aggregates and analyzes rep activity across calls, emails, and CRM records to provide a complete performance profile.

How it helps reps:

Representatives receive immediate, automated feedback following every call, clarifying their current performance level and specifying areas where improvement is needed.

Pros:

  • Automatically scores sales conversations, highlighting both successful and unsuccessful rep behaviors.

  • Integrates with CRM, call recording, and email tools to construct a comprehensive view of each representative’s performance metrics.

  • Offers personalized training suggestions based on the representative's individual strengths, weaknesses, and performance within active deals.

Cons:

  • Automated scoring may struggle to capture the full context of nuanced or highly technical customer conversations.

  • The precision of training recommendations is dependent on available data volume; low call activity may compromise accuracy.

Standout feature: Training Library

Wonderway features a collection of ready-to-use training modules developed by leading sales experts in the technology sector. These programs are fully customizable to align with your product, industry, and team structure, facilitating a rapid rollout of new training content.

Pricing: Custom pricing based on the chosen plan.

9. Hyperbound - AI Sales Roleplays & Real Call Scoring

Best for: Sales organizations aiming to scale their onboarding, coaching, and hiring efforts using a unified AI system.

Hyperbound is an AI sales coaching platform that helps teams systematize and scale the best practices of their top performers. It examines thousands of your historical sales calls to uncover successful patterns, which it then uses to construct highly realistic roleplay simulations that representatives can practice on demand.

The platform also includes automated call scoring, customized coaching feedback, and comprehensive call analytics, giving managers transparent visibility into rep performance and required support areas.

How it helps reps:

Reps can sharpen their selling skills through hyper-realistic practice, receive AI-generated feedback grounded in their actual call performance data, and accelerate their ramp-up time via customized onboarding sequences.

Pros:

  • AI roleplay is available in over 25 languages, simulating authentic buyer interactions to boost consistency and confidence.

  • Automatically scores both live and recorded sales calls, providing granular, customizable feedback tied directly to your adopted sales methodology.

  • Integrates smoothly with Salesforce, Gong, Outreach, Salesloft, Orum, and major meeting platforms like Zoom and Google Meet.

  • Practice recommendations and skill gap analytics empower managers to focus their coaching efforts where they will have the greatest impact.

Cons:

  • The extensive feature set might be more than is necessary for smaller or early-stage sales teams.

  • Requires a dedicated time investment upfront to align the AI with your internal sales playbooks.

  • Representatives who are new to AI-led coaching may need time to adapt to this learning style.

Standout feature: AI-Powered Hiring Assessments

Hyperbound can evaluate job candidates using AI-driven roleplay scenarios and scorecards that mimic real-life sales situations. This allows leaders to objectively assess a candidate’s pitching ability, objection handling, and coachability before extending an offer.

Pricing: Custom pricing tailored to organizational requirements.

10. Quantified - AI Roleplay & Coaching

Best for: Enterprise sales organizations seeking to scale realistic pitch practice and coaching without overextending their managerial resources.

Quantified is an AI sales coaching platform that allows representatives to practice conversations with incredibly realistic, role-specific AI buyers. The system creates customer scenarios precisely tailored to your company’s industry, product line, and specific sales motion, then evaluates each representative's performance using metrics focused on customer perception, negotiation effectiveness, and solution expertise.

How it helps reps:

In contrast to tools that only analyze past call recordings, Quantified emphasizes proactive skill development. Reps can rehearse critical sales moments, receive personalized feedback, and build essential muscle memory in a secure, controlled environment before engaging with live prospects.

Pros:

  • AI-powered roleplays simulate authentic buyer interactions based on your defined ideal customer profile (ICP).

  • Accelerates ramp time and improves message consistency by reinforcing key skills and messaging in a real-time practice setting.

  • Scalable reporting allows sales leaders to track performance metrics across individuals, teams, and key subject areas.

  • Integrates with essential tools like Google Workspace, Microsoft 365, Zoom, and Teams.

Cons:

  • Requires initial time to configure simulations and scoring to perfectly align with your specific sales process.

  • May not be the optimal fit for small teams lacking the bandwidth to actively monitor rep progress and ensure follow-through on coaching.

Standout feature: Customizable Rubrics

Quantified assesses representatives against bespoke rubrics that accurately reflect your unique sales messaging, skills, and desired sales behaviors. These rubrics drive detailed feedback and team-level reports, enabling managers to precisely identify strengths, spot organizational trends, and optimize coaching across the entire sales force.

Pricing: Custom pricing.

11. PitchMonster - AI Roleplay for Cold Calls, Demos, and Discovery Calls

Best for: Sales leaders prioritizing rapid rep ramp-up and the scaling of personalized roleplay coaching for early-stage selling.

PitchMonster is a specialized AI roleplay platform built to help representatives practice high-value, early-stage conversations, including cold calls, discovery dialogues, and product demonstrations, within a controlled setting. Its simulations are completely customized to your actual ICPs, sales stage requirements, and common objection scenarios, ensuring reps practice exactly what they will encounter on live calls.

You can upload your company’s coaching benchmarks, pitch models, and scoring rules, or utilize the platform’s built-in templates and scorecards. The AI provides personalized feedback instantaneously, regardless of whether a rep runs 10 or 10,000 roleplays per day.

How it helps reps:

Reps can practice high-pressure conversations whenever they need to, receive immediate, contextual feedback, and refine their pitch delivery without requiring direct manager supervision.

Pros:

  • Simulates cold calls, demos, and discovery conversations based on real-world ICPs and messaging frameworks.

  • Delivers instant, AI-generated feedback that adheres to your custom coaching criteria.

  • Features a library of professionally designed roleplay exercises for rapid training deployment.

  • Allows for self-coaching, as reps can review suggestions and iterate their performance before a manager review.

Cons:

  • Best suited for organizations that already have well-defined playbooks or frameworks ready for immediate upload.

  • Some representatives may need time to adjust to AI-driven coaching compared to direct manager feedback.

  • Roleplay practice exists in isolation due to limited connection to real-life conversation intelligence and deal data.

Standout feature: In-built AI Speech Coaching

PitchMonster functions as a "Grammarly for sales communication." It provides representatives with immediate guidance on crucial vocal qualities like pacing, clarity, sentence structure, and the overuse of filler words, helping them sound more articulate, persuasive, and professional in every conversation.

Pricing: Custom pricing based on the number of licenses purchased.

12. Momentum - AI Coaching & Workflow Automation

Best for: RevOps leaders and sales managers who want to unify AI coaching with real-time workflow automation integrated into platforms like Slack and Salesforce.

Momentum is a sales coaching and operations platform that combines conversation intelligence, performance metrics tracking, and go-to-market automation. It assists managers in providing more effective coaching through AI-scored calls, monitoring skill development over time, and delivering feedback directly on meeting recordings.

How it helps reps:

Representatives receive feedback on their calls, insights to help refine their selling techniques, and proactive alerts to take necessary actions during or immediately following conversations.

Pros:

  • AI-scored calls include granular skill tracking and threaded manager comments for detailed feedback.

  • Aggregate dashboards enable managers to track performance trends and coaching impact across the team.

  • Deep Slack integration facilitates real-time updates, proactive nudges, and centralized deal room collaboration.

  • Helps automate routine CRM and workflow tasks, significantly reducing administrative burden on sales representatives.

Cons:

  • Requires a meticulously clean CRM environment and strongly defined processes to fully capitalize on automation benefits.

  • Primarily optimized for organizations utilizing both Slack and Salesforce.

Standout feature: Workflow Automation

Momentum extracts key insights from all customer interactions (calls, emails, chat, and tickets) and automatically updates relevant CRM fields. It routes deal risks, updates, and associated tasks to the correct individuals in Slack, automatically sets up deal rooms, and triggers subsequent workflows based on the real-time activity within the deal.

Pricing: Subscription plans range from $\$69 /$ user/month to $\$99 /$ user/month. A custom enterprise tier is also available.

Strategies for Enhancing Your Sales Training and Coaching

As you develop your sales training and coaching initiatives, incorporate these key principles:

Develop High-Impact Training Resources

The quality of your training content can directly determine the difference between an average performer and a top revenue generator. Data indicates that only 10% of top performers report not having a formal training program, while 30% of underperformers state their company lacks one.

With Proshort's Admin Course Creator, you can generate training materials in a fraction of the time. Simply define the course structure, and the platform’s AI will help build the curriculum, quizzes, and learning assignments. For example, by specifying a skill need, you can leverage the Playbook section where AI automatically summarizes and clusters common objections, linking them to real video snippets of successful peer responses to create an instantly usable, rep-ready resource.

Embed Learning Directly into the Workflow

Proshort delivers contextual, just-in-time guidance by surfacing critical sales information directly within the tools and moments representatives use most. Instead of mandatory, lengthy training sessions, representatives receive concise, relevant information exactly when they need it, such as in the Meeting Prep Card right before a call.

The outcome is ongoing, contextualized learning that is easier to absorb, faster to apply, and perfectly aligned with how representatives actually conduct business.

Prioritize Personalization in Development

When training and coaching are personalized, representatives spend less time reviewing concepts they already understand and more time building the precise skills necessary for their role.

Every representative possesses a distinct learning style, professional background, and set of abilities. Tailoring their development path ensures they are continually improving in ways that align with their personal objectives and the organization's revenue goals. Proshort achieves this through its Rep View and Agent Skills section, which highlights skill gaps and automatically suggests AI Roleplay or peer snippets to address those specific deficiencies.

Provide Constructive Feedback and Recognition

Approximately 65% of representatives state that support from sales leadership is the most critical factor in helping them achieve quota. Therefore, sales training cannot be a passive, "set it and forget it" initiative. Sales leaders must provide consistent, constructive feedback and build clear growth paths informed by individual performance.

Consider utilizing Proshort's Manager View to hold structured where you review the rep’s Skill Score trend and the strategic observations/recommendations from their top 5 deals. Additionally, leverage Meeting Snippet Conversion to share successful moments with the team, celebrating progress and helping to foster a motivated, high-performing culture.

Measure the True Impact of Training

Nearly $20\%$ of companies report having no visibility into how engaged their representatives are with training materials. This lack of insight can severely undermine performance and retention efforts. Sales leaders who achieve high retention are almost $30\%$ more likely to keep new representatives for over a year when they maintain clear visibility into training engagement and its impact on revenue.

Tracking the right sales data—like the relationship between a rep’s Skill Score and their Revenue Won in the Rep View—helps you understand which enablement activities are effective, which are not, and where adjustments are needed. When you can accurately measure training impact, you can continually refine your programs and set your team up for long-term success.

Empower Your Sales Training with AI

AI has fundamentally changed sales training and coaching paradigms. Instead of outdated, generalized programs, representatives now receive personalized development, real-time insights, and immediate feedback precisely when needed. From sophisticated AI Roleplay to detailed conversation intelligence and automated coaching, modern tools help sales teams ramp up faster, maintain alignment, and close deals more efficiently.

Proshort unifies these capabilities with contextual enablement that integrates directly into the platforms your team relies on. Whether they are reviewing a deal in the Deal View, preparing for a meeting via Meeting Prep Cards, or practicing a skill with AI Roleplay, Proshort surfaces the exact content and guidance needed at that moment.

No more tedious tab-switching. No more endless searching. Just the right intelligence at the right time.

Ready to see how Proshort can revolutionize your sales execution and coaching? Book a demo today.

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Ready to supercharge your sales execution?

Shorten deal cycles. Increase win rates. Elevate performance.

pink and white light fixture

Ready to supercharge your sales execution?

Shorten deal cycles. Increase win rates. Elevate performance.

pink and white light fixture

Ready to supercharge your sales execution?

Shorten deal cycles. Increase win rates. Elevate performance.

pink and white light fixture