New to 2Win? Learn About Us!

That's not just a line we use, it's a legacy we've earned.

Demos are not what they once were. When we were founded, complex software demonstrations lasted days, took place in person, and were the product of hundreds of hours of research. Times have changed.

We're proud of how we've expanded beyond demos into customer success, executive communication, and discovery training, and we're even more excited about where we're going. What hasn't changed is our foundation: communicating with clarity, using storytelling to engage, and equipping others to earn and keep attention. Even as the way we train transforms, those values remain constant.

Before we discuss the modern seller's journey, let's take you back to the beginning of ours.

Where We Started

In 2001, Bob Riefstahl founded 2Win! after more than two decades in presales and solutions engineering. His mission? To teach teams how to run compelling software demos that win business. He identified common missteps—"demo crimes," as he called them—and introduced a structured, repeatable methodology to help sales teams present with purpose and clarity. His book, Demonstrating to Win!, quickly became the playbook for presales professionals worldwide.

As the methodology gained traction, the team grew. Ron Kendig, John Coker, and Chad Wilson each joined to build out 2Win's operational strength, facilitation talent, and global sales infrastructure. Together, they scaled the original vision, bringing 2Win to teams worldwide. When Dan Conway stepped in as CEO, innovation accelerated. Dan introduced new offerings like 2Win ongoing guidance (our annual certification and coaching system), 2Win Consulting (our go-to-market transformation practice), and Wyn, our AI-powered coaching agent.

Who We Are Today

Our current leadership reflects our evolution from a founder-led movement to a modern, mission-aligned organization delivering training that scales with your business:

• Dan Conway — CEO: Guides global expansion and strategic innovation.
• Chad Wilson — VP, Operations: Oversees curriculum development, marketing, partnerships, and GTM.
• Ron Kendig — VP, Facilitation & Consulting: Leads our world-class coaching team.
• John Coker — VP, Worldwide Sales: Drives customer relationships and business growth.

Highlights of Our Evolution

• Bob Riefstahl releases the book, Demonstrating to Win! (2000)
• Bob Riefstahl + Ross Jacobsen found the company and our flagship training, Demo2Win!, is born (2001)
• Ron Kendig joins to build global facilitation (2004)

• Dan Conway becomes CEO, leading organizational readiness and growth (2012)
• Chad Wilson expands curriculum reach and effectiveness (2013)
• John Coker joins to expand sales operations (2013)

New Standards for Demo Excellence

Demos today are no longer one-time events—they're continuous, multi-touch experiences that span the entire customer journey. Demo2Win transformed with this shift, growing to meet broader needs across entire sales organizations. We now offer training for SaaS, asynchronous demos, customer success, and product-led growth motions, all grounded in our methodology and updated to reflect modern buyer expectations.

Traditional soft-skill training rooted in behavioral science will always inform our approach, but how we deliver that training, via AI coaching agents or live facilitators, continues to evolve. Buyers gather information asynchronously, value is delivered across time zones, and teams must communicate across formats. So we teach teams how to make every moment count, from a product teaser on your homepage to a guided in-app tour after the sale.

Why It Works, and What We're Still Learning

Our methodology has stood the test of time because it adapts. Today, we coach not just on features but on framing transformation. We teach customer success teams to drive renewals and adoption while making real commercial impact. We train sellers to guide live, virtual, and AI-supported conversations. We help product marketers build content that connects.

We built Wyn, our AI-powered coaching agent, to make high-quality coaching available every day without requiring anyone to add it to their calendar. Live coaching and AI aren't mutually exclusive—they complement each other to complete the coaching loop. Wyn reinforces training between sessions, gives instant feedback, and tracks performance trends across reps.

Built by People Like You

We're proud of our roots and excited to share our roadmap with you. What drives us isn't just demo skills—it's the lives we've changed and careers we've impacted along the way. Our culture is rooted in winning, but also in humility, authenticity, and the belief that everyone can improve in client engagements. This journey was built by sellers, for sellers. And it's just beginning.

If you're curious about what the next generation of sales enablement looks like, let's talk.