The Next Generation for Scaling Sales Coaching

We know that top-performing sales organizations prioritize ongoing coaching and development. Data shows that 96% of go-to-market leaders agree that "the right sales coaching can make a significant difference in performance"; yet, only 5% of front-line managers' time is spent coaching and mentoring their teams. 

As organizations scale to meet goals, continued coaching quickly takes a backseat. Placing the responsibility to maintain consistency and reinforce core techniques on your already overloaded frontline managers is no longer working.

Over the last three decades, we've equipped thousands of revenue teams with the necessary tools to win more deals. Still, we've seen the gap in reinforcement continue to grow, until now.

Developing Fluency in 2Win Curriculum. 

Picture this: you're taking a dream trip to Italy and want to learn the language. You dive into training to learn the fundamentals of the language, even earning a high score on Duolingo, but when you arrive in Italy, transferring what you've learned in practice to real life is rocky at best.

It's the same with 2Win curriculum. Maximizing your success with the tools we provide requires ongoing practice and coaching. In today's landscape, managers are spread thin, feedback isn't timely, and coaching continues to be deprioritised; until now.

Though we provide post-training access to curriculum to build fluency, the onus was still placed on frontline managers to make it happen. It was time for us to bridge the gap.

Filling The Live Coaching Gap 

2Win training is so effective because participants get the opportunity to practice during training and receive direct feedback in real-life scenarios. Live coaching and mentoring scenarios, like learning a language in a foreign country, offer new and different situations that shorten the time to become fluent and easily converse on various subjects, ie, adapt to new situations. 

For reps, SEs, and customer success managers to increase their capacity to move conversations forward in a direction, adapt to new scenarios, and increase sales velocity, they need practice.

Our chief barrier to fluency has always been the time limitations of 1:1 training and mentoring. Now, we have a revolutionary update that provides innumerable live coaching and sales scenarios simulations through the 2Win AI Coaching Agents. 

The pressure of live calls, the rush of a packed pipeline, and the lack of immediate feedback mean even your best reps struggle to retain what they’ve learned. AI coaching from 2Win can be a trained shoulder to lean on. - Pull quote 

Meet the 2Win AI Coaching Agents

What does an AI-driven experience mean for your team’s fluency in 2Win training? The AI Coaching Agents think, speak, and understand presales, sales, and customer success scenarios from objection handling to discovery, which is the key to training fluency.

Our AI Coaching Agents are trained in 2Win’s proprietary techniques, built with a deep understanding of how top reps communicate, demonstrate, and differentiate in the sales cycle. The AI Coaching Agents listen, analyze, and offer real-time feedback, helping develop strengths and suggest refinements.

Reps can practice with AI Coaching Agents to:

• Uncover business value using CDIM.

• Dry run a demo and get feedback rooted in the Demo2Win methodology.

• Practice managing objections and difficult client interactions.

• Simulate real-life client engagements over multiple meetings with multiple personas. .

• Drive expansion revenue by communicating Value Realization based on a Success Plan. 

One of the least talked about, and most impactful issues in sales training is the willingness of sales professionals to undergo training and practice new skills as a team. Resistance to change, even if it could dramatically speed sales velocity and ramp your career, is entirely normal. Many reps prefer private training for this reason. AI Coaching Agents offer a private environment that can dramatically grow and adjust selling styles for the better.

Core 2Win Techniques Reinforced by AI

We train using proprietary, proven frameworks. The AI Training Agent is trained in all proprietary 2Win trainings; however, to give you an idea of two of the most impactful techniques for improving fluency, the CDIM framework and Tell Show Tell are great examples. 

Discovery On-The-Fly with CDIM Discovery Framework 

The CDIM™ Discovery Framework—standing for Current, Desired, Impact, and Metric—is a structured method for guiding customer conversations. It is taught in Discovery2Win, Winning with Executives, and Success2Win, and it uncovers how a customer is currently solving a problem, what they ideally want, why that change matters, and how success is measured. It is a logical progression that keeps conversations organized and builds trust. The catch: it requires two people to practice. 

The AI Coaching Agent helps master CDIM™ by offering adaptive roleplay scenarios, providing instant feedback on question phrasing, tone, and flow, and helping users refine their approach. The agent can simulate various customer types, roles, industries, and challenges, giving reps repetitive yet dynamic practice. It can analyze performance, flagging missed opportunities or weak transitions, and offer coaching tips to build fluency and confidence in real-world conversations.

Tell-Show-Tell 

One of 2Win’s core training techniques from the Demo2Win course is Tell-Show-Tell. Tell-Show-Tell turns a demo into a strategic, audience-centered experience that advances deals and shortens sales cycles. It is a structure for showing features while guiding the audience through a meaningful and value-driven narrative: Tell (set context and relevance), Show (demonstrate how your solution solves their problem), and Tell again (highlight impact and next steps). When this rhythm and structure is applied, demos are more purposeful, focused conversations that drive engagement and improve outcomes. 

Adhering to Tell-Show-Tell and not becoming distracted by questions from the audience or stakeholder objections takes a lot of practice. Formerly, this practice and expertise were only available in live training. With the AI coaching agent from 2Win, practicing and mastering Tell-Show-Tell becomes easier and more scalable. Sellers rehearse structure and play out scenarios with instant feedback on structure, clarity, and value messaging. This builds fluency at their own pace and does not require scheduling and facilitation. Additionally, you can assign practice prompts, track usage, and monitor progress as managers. 

Real Practice. Real Impact.

Are you ready? Coaching at Scale

Some of the impacts you can anticipate are faster ramp times for new reps, higher demo-to-close conversions, and more confidence in live selling situations. Additionally, scaling benefits include consistency across global teams and reinforcement in organizational practices. Technique can become a common language of sellers, which is the future of sales excellence. Your team needs structured, repeatable, and immediate feedback loops that turn technique into habit.

Request a consultation and learn how 2Win programs and the 2Win AI Coaching Agent can deliver a scalable way to build fluency in the proven 2Win frameworks—like CDIM and Tell-Show-Tell to turn training into tangible performance.