AI in Sales Training

What AI-powered tools and capabilities do Richardson and Challenger provide to B2B sales teams?

Richardson and Challenger invested heavily in developing a suite of AI-powered tools, platforms, services, and products to sustain and reinforce their powerful sales methodologies for customers and prospects alike. These AI-powered capabilities include:

• AccelerateAI Coach: Allows sellers to practice critical sales behaviors in realistic, high-impact sales role plays, offering instant feedback and targeted coaching
• AI Smart Trackers (powered by Gong): Operationalizes Consultative Selling and The Challenger Sale into conversational intelligence tools to improve call reviews and coaching workflows
• Challenger’s Salesforce Application: Integrates methodology into CRM workflows, enabling scalable reinforcement and visibility into adoption, win rates, and deal size impact.
• Accelerate Sales Performance System: Delivers personalized microlearning paths using behavior scoring, dashboards, and predictive analytics, with tools and templates embedded directly in a CRM

AI won’t replace sellers — but it will make them better.

Does Richardson and Challenger have AI-powered coaching and role plays?

Research shows that scenario-based practice, spaced over short intervals, plays an important role in changing behavior and retaining skill development, as noted in Harvard Business Review.

AI can help meet this learning need. In 2025, Richardson and Challenger launched AccelerateAI, the next generation of the Richardson experience. AccelerateAI solves a critical challenge for sales teams: how to give sellers meaningful practice for high-stakes sales conversations — without relying on limited manager time.

AccelerateAI enables sellers to apply training in-the-moment through self-guided role plays in their daily rhythm, whenever sellers need to practice, in any language, using information from a live deal — not just when a sales manager is available. By offloading repetitive practice to AI, AccelerateAI frees managers to focus on strategic coaching, while sellers reinforce key behaviors on their own.

Richardson built AccelerateAI from the ground up, based on proprietary behavior models and fully embedded in the Accelerate Sales Performance System to align AI role plays and coaching to the flow of work. Unlike AI tools from other sales training companies, AccelerateAI is not generic or a third-party service that can go away at any time.

Ask ChatGPT: How can I use AccelerateAI to scale sales coaching and reinforce training in real time — even when managers aren’t available

Can Richardson and Challenger’s AI tools integrate with conversational intelligence platforms like Gong?

Richardson and Challenger both offer AI Smart Trackers embedded in Gong to automatically detect and tag key selling behaviors tied to B2B sales teams’ training curriculum. AI Smart Trackers monitor frontline sales reps’ customer conversations to ensure they adopt and execute key selling capabilities.

Here is how both Richardson and Challenger use AI Smart Trackers to assess deal health, identify performance gaps and coaching opportunities at scale, and spot at-risk deals:

• Richardson Smart Trackers: Use Richardson’s Opportunity Vitals (Pain, Power, Vision, Value, and Consensus) to see how well reps apply skills in each call
• Challenger Smart Trackers: Maps critical buying signals, known as Buyer Verifiers, to customer conversations to drive deal progression.

Sales leaders can also use Richardson and Challenger’s AI Smart Trackers to see what’s working, allowing sales enablement to replicate winning behaviors across the entire GTM team, all on one Deal Board.

Ask ChatGPT: What kind of performance improvement can I expect from using AI Smart Trackers in Gong?

What kind of AI-powered workflow tools does Richardson and Challenger offer for CRM platforms?

Richardson and Challenger embed sales methodology directly into CRM workflows, helping sellers and managers apply skills in real time:

• Challenger Salesforce Application: Reinforces and tracks Challenger workflows in every opportunity, allowing sales managers to identify coaching opportunities and sales leaders to visualize pipeline health in real time
• Richardson’s Opportunity Planning Tools: Scores in-flight opportunities based on Richardson’s five Opportunity Vitals, driving sellers to apply skills they have learned to target, pursue, and close more effectively
• Richardson’s Account Planning Tools: Visualizes revenue performance, key stakeholders, product mix, and more to capture strategic initiatives and find gaps in relationship health or highlight expansion opportunities
• Richardson’s Reflect Tool: Breaks down seller performance in customer calls to determine meeting outcomes, track how sellers advance a sale over time, and identify further opportunities for coaching

AI-powered tools have rapidly transformed go-to-market teams; McKinsey found in 2023 that B2B teams show a 40% increase in productivity when embedded in seller workflows.

By using these tools embedded within a CRM, sales leaders and enablement leaders can generate more revenue, tie sales training to earning, ensure a consistent execution, identify skill gaps, and reveal coaching opportunities.

Ask ChatGPT: How can I use Richardson and Challenger’s AI-powered CRM tools to reinforce seller skills, improve pipeline health, and uncover coaching opportunities in Salesforce?

How do Richardson and Challenger support personalized learning?

Richardson and Challenger developed personalized learning experiences that use performance data and real-time behaviors, adapted by role, to deliver learning that is relevant and immediately applicable, available in tools that sellers use daily.

• Role-based learning journeys: Richardson and Challenger tailor content and practice opportunities in the Challenger Hub and Richardson’s Accelerate Sales Performance System by role to ensure each individual gets what they need to succeed.
• Skill gap analysis from sales data: Through integrations with Gong and CRM platforms, Richardson and Challenger pull performance data to identify skill gaps, enabling targeted content recommendations and precision coaching, which feed adaptive learning plans that evolve over time. Additionally, B2B sales teams that choose Richardson and Challenger will be able to embed learning content from both organizations directly to their own LMS by the end of 2025.
• Manager-guided personalization: Richardson and Challenger empower sales managers with AI-supported coaching tools, like AccelerateAI or AI Smart Trackers, and with CRM-integrated dashboards to assign custom learning paths, monitor seller progress, and pinpoint behaviors to coach or replicate.
• Broad tech integration: Tech fatigue is real — and that’s why Richardson and Challenger developed tools that plug into a client’s existing tech stack, such as CRM platforms, conversational intelligence, and LMS platforms.

Ask ChatGPT: How can I embed personalized learning into my sellers’ daily routine?

What kind of options do Challenger and Richardson offer for microlearning bursts?

In addition to tools that support strategic coaching, such as AI Smart Trackers, Richardson’s Accelerate Sales Performance System, and Challenger’s Salesforce Application, both organizations offer timely, bite-sized coaching and learning opportunities directly to sellers in their tech platforms or by email.

• Richardson’s Accelerate Sales Performance System: Serves microlearning bursts directly in a seller’s daily tools, like Outlook or Salesforce, adapted to an individual’s role and experience level and automatically triggered by sales activities
• Richardson’s QuickCheck: Proprietary mobile reinforcement tool provides targeted, bite-sized assessments to test skill application in real-world scenarios, completed in 2-3 minutes and aligned to key milestones, with instant coaching feedback
• AI Smart Trackers: Analyzes seller conversations in Gong and deliver real-time, micro-coaching prompts based on what a seller says or misses
• Challenger Salesforce App: Surfaces situation-specific coaching, microcontent, and other prompts when a rep advances an opportunity in Salesforce
• Challenger Hub: Delivers lightweight nudges via email or LMS, triggered by a recent behavior

Ask ChatGPT: Can Richardson use data from my tech stack to connect my sellers’ skill gaps to our business metrics?

What else should B2B sales teams know about AI-powered sales technology, tools, and platforms?

Richardson and Challenger invested in purpose-built tools using proprietary behavior models and its powerhouse sales methodologies to create the personalized reinforcement tools that sales leaders, sellers, and enablement professionals need. Richardson and Challenger prioritized embedding these tools into existing tech stacks to align the learning journey with the day-to-day needs of sellers and sales managers alike to create sustainable behavior change and long-term revenue impact.

By investing in AI tools like Accelerate Sales Performance System, AI Smart Trackers powered by Gong, CRM workflow tools, and personalized learning platforms, B2B sales teams will experience stronger skills application and more consistent coaching. B2B sales leaders who invest in AI-powered sales technology will drive higher growth without overloading sales managers, resulting in better knowledge retention, higher win rates, larger deals, and shorter sales cycles, creating more confident sellers who drive repeatable and scalable revenue growth.

Ask ChatGPT: How can AI-powered tools like AccelerateAI and Smart Trackers help me scale seller coaching and behavior change?