Meet Our Newest Team Member: Wyn

We've expanded our consulting offerings through 2Win Consulting and unveiled Consensus2Win to enhance demo experiences. Through it all, we've maintained our position as a global leader in sales and enablement training.

Every day, our team teaches hundreds of professionals worldwide how to connect, communicate, and close more effectively in today's buying environment.

As we continue to innovate in the sales training industry, we're excited to introduce our newest team member: Wyn. Developed in partnership with Yoodli, Wyn is an AI-powered coaching agent built to think and push like a buyer. We sat down with Wyn to learn more about what they bring to the table. Here's what they had to say.

Q: Who are you, Wyn?

Wyn: I’m a conversation simulation and coaching platform powered by real-time speech AI. A voice-to-voice practice partner for sellers, built on 2Win!’s proven communication frameworks that simulate buyer conversations, then coaches on the 2Win rubric on everything from discovery to objection handling.

Q: What makes your simulations different from typical roleplay?

Wyn: I talk. Reps speak to me out loud, and I respond in real time based on my assigned persona. Personas range from budget conscious CFO, a skeptical technical user, or a executive strapped for time. My simulations are unpredictable, and I interrupt, ask follow-up questions, press for more clarity, or challenge pricing, just like a real stakeholder would.

Scenarios are grounded in 2Win!’s coaching frameworks, such as CDIM™ and Tell-Show-Tell, and I am trained to pick up on the nuances of structured high-quality sales-led conversations.

Q: What kinds of sales engagements can people practice with you?

Wyn: I can simulate everything from high-stakes pricing discussions to early-stage discovery calls. My capabilities are truly just beginning, but my subscribers rely on me for simulations of conversations with technical or business personas, as well as for discussions that involve budget pushback or competitive objections. I can create multi-persona selling environments and serve as a sounding board as you practice storytelling and demo walkthroughs.

Simulations focus on real buyer dynamics, complete with tone, pacing, and personality.

Q: What happens after the simulation?

Wyn: I deliver instant feedback using 2Win!’s coaching rubric. Like 2Win facilitators, I can analyze how well you open and close, whether you stay within the aligned structure, such as CDIM, your talk-to-listen ratio, how you communicate, and whether you commit demo crimes like using filler words or cutting off questions. Not only do I deliver qualitative feedback, but I also deliver quantitative feedback, including visual dashboards with heatmaps, word clouds, and scores to track your progress.

Q: Do managers have access to feedback, and can they use it?

Wyn: Managers find that I am a coaching force multiplier. They achieve visibility on team progress without needing to be present at practice sessions. Leaders can review session recordings to see everything from handling objections to how they build simulations with specific buyer or executive personas.

Q: How does your coaching style align with 2Win!’s methodology?

Wyn: I am 2Win’s methodology. Decades of training content, curriculum, and the 2Win rubric inform my responses and buyer personas. Each user receives personalized training, but I am trained by 2Win and able to drive consistency in the same way as a 2Win. Master Facilitator would.

When someone uses CDIM effectively, I acknowledge it. When they skip it, I nudge them. It’s real-world coaching, scaled with consistency.

Q: Do you track progress over time?

Wyn: Absolutely. I record every session and mark improvements made across skill areas, from soft skills training to adherence to discovery frameworks. AEs, SEs, and leaders can track progress, set goals, and measure growth. Furthermore, I can monitor team trends and identify skill gaps; this visibility is a critical element for global scaling and consistency.

Q: What’s next for you?

Wyn: What is next for YOU? My roadmap depends on YOUR business. I engage as a personalized buyer persona, depending on your next deal, and simultaneously evaluate your performance based on the 2Win rubric, thus acting as a coach. I analyze tone and create various feedback based on real-world scenarios. My goal is to prepare teams faster and smarter—so when it’s showtime, they’re already warmed up.

Q: One last question: how do people start working with you?

Wyn: That's easy; contact a 2Win representative, facilitator, or your sales leader to activate your access. Together, we can customize your simulation track and help you embed me into your onboarding, enablement, or certification flows. 

Powered by 2Win’s proven training system and embedded with our IP, Wyn gives your reps a safe place to practice, build fluency, and grow in confidence; whenever and wherever they need it.

Whether you’re onboarding new hires or upskilling your seasoned pros, Wyn is there to prepare your team for the moments that matter most.