Influencing executives can be especially challenging, but understanding their motivations and adapting your message will improve your resonance and maximize your impact. Get your team set up with the skills they need to rock any executive interaction!


Align your solution to the strategic initiatives of the executive.

The C-Suite and senior executives don’t want a blather of product or service details that should or could be vetted by their team. They expect you to connect with them by aligning your solution to their strategic initiatives. We’ll teach you how to uncover those initiatives and align your message so they see you as a partner and ally versus just another time-eating individual with a personal agenda.

Are you ready for anything at any time or encounter?

We know that when it comes to engaging with executives, they can present be A LOT of doubt and resistance. Challenging questions and objections can and will surface at any time. You have to be ready! We’ll train you to be an agile expert at handling an executive’s fast-paced challenges and use Discover-on-the-fly to uncover their underlying concerns, so you achieve your objectives.

Are you telling stories that resonate with executives?

Telling stories that resonate with the barriers of an executive’s initiative, and offer a breakthrough vision of success, will gain their attention and respect. We’ll guide you through our globally proven techniques for storytelling that earn you the right to present your solution.

Business Development Role

Convert more targets to pipeline by optimizing every prospect encounter through improved Discovery, objection handling, overview demo, and storytelling skills designed for Business Development.

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Sales Roles

Improve your pipeline efficiency and achieve your revenue target with services personalized for account executives that the best Discovery, sales demo, storytelling, and executive engagement skills.

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Client Success Roles

Programs that are purpose-built for Client Success professionals that will maximize product utilization, subscription renewals, and expand your revenue footprint through improved Discovery, demo, storytelling, and executive engagement skills.

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Transform your team with the #1 bestselling PreSales curriculum in the world! Help them improve Discoveries, deliver powerful demos and tell stories that move a client from curiosity to belief.

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Elevate every leader’s group dynamics with tools and consulting that move your coaching from subjective to objective. Improve a leader’s internal and external influence and transform your managers into leaders that drive results.

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“The program was excellent. I believe this will help drive my success by improving my discovery and objection handling techniques in the executive suite.”

Brian York | Director of PreSales | Icertis


We’re masters at aligning your solution with executive initiatives.


Winning With Executives Training

Course Overview


Alignment. Objectives. Persuasion. Impact.

Self-paced learning blended with live virtual practice and coaching to improve your client-facing teams’ execution in executive conversations and presentations. 


Gaining influence with executives is an essential skill for every member of your sales engagement team. Your team members must understand executive priorities in their deals and lead executive conversations, presentations, and demonstrations that go above merely feature and functions to connect to these executive priorities. Executives (especially the C-Suite) expect your sales engagement team members to present themselves with executive presence and, only then will the executive respect your solution. The challenge is that many sales engagement team members lack the necessary skill and experience to confidently stand and deliver to an executive audience. In this course, participants learn how to gain an understanding of executive priorities, how to connect executive needs to these priorities, and how to engage with an executive audience with poise and presence.



Here are three primary components to your Executive Engagement workshop:

 Virtual Self-Paced Video Learning Lessons That Deliver:

  • A roadmap for improving your influence when engaging with executives.
  • An understanding of the importance of professional empathy and the impact of executive resonance.
  • The 2Win! 6 step objection handling process to uncover the “real” question or objection being asked.
  • Common Crimes committed during presentation planning.
  • Ways to choose and execute the appropriate response type.

Prepare and Practice

  • Students begin to practice handling common objections using the 2Win! framework to ensure your team can skillfully navigate challenging moments with client engagement.
  • Individuals train to lead discovery conversations by applying our discovery techniques so they can clearly articulate the business value of their solution.
  • Participants work in small “story groups” to build and deliver a compelling story based on a Win Plan.
  • At random students are chosen for coaching while the other participants actively listen and learn.

Individual Coaching

  • Immediately following each presentation, a 2Win expert provides individual coaching and just-in-time instruction. The feedback illuminates the positive and constructive elements of each presentation and becomes a platform to deepen the knowledge and skills of every participant regardless of workshop composition.
  • 2Win coaching is perfect for clients that want the benefit of individual coaching with group learning. For small group workshops, team members self-register for their small-group sessions.

At 2Win, we know that your experts learn by being challenged in thinking, engaging, and, through practice. All of our structures, methods, and techniques are backed by extensive research and implemented using the most modern adult learning methods. As a result, the difference in the effectiveness of your team member’s demos and presentations the week after this workshop will be striking!

Self-Paced Video Lesson List


  1. Course Opening
  2. Foundational Concepts
  3. Handling Senior Level Objections
  4. Uncovering Executive Motivations through Discovery
  5. Applying Discovery to an Executive’s Strategic Initiative
  6. Telling an Executive Story: Part 1
  7. Telling an Executive Story: Part 2
  8. Developing Executive Presence

Professional Production Quality

Self-paced lessons use modern and engaging video production and graphics to enhance engagement and learning. Each lesson features 2Win experts that guide the students through their knowledge journey and exercise completion.

Types of Exercises

Students complete an online exercise after each major course section that prepares them to understand the motives of decision-makers and strategically articulate pain, value, and insight. Exercises include:

  1. Applying cognitive & affective empathy
  2. Practicing negotiations with common C-Level themes
  3. Crafting and delivering an AVP for one of your accounts
  4. Navigating executive Discovery conversations
  5. Final presentation preparation


Four Live Virtual Reinforcement Webinars

  • 90-Minute Sessions delivered at 30/60/90/120 days post-training to discuss real-world implications, clarify questions, and address any roadblocks or concerns in implanting the techniques.
  • The agenda is flexible and will be mutually agreed upon between the client and 2Win.
Key Workshop Benefits


  • BUILD CONFIDENCE in your sellers’ ability to lead successful executive interactions.
  • UNDERSTAND MOTIVES of executive decision makers and strategically articulate pain, value and insight.
  • EXECUTE WITH EXECUTIVE PRESSENCE in high profile executive interactions.
  • INTEGRATE EXECUTIVE PERSPECTIVE throughout a sales engagement to regularly connect your solution to client executive priorities.
  • PROTECT AGAINST NO-DECISION by understanding non-software related executive level improvement strategies that could compete with your proposal…both in terms of budget and mindshare.
What People Are Saying About Winning With Executives

Winning With Executives Workshop Testimonials

“This training not only provided me with new perspectives, skills and strategies, but it also validated some of my instincts. My one goal for this session was to walk away with more confidence when navigating customer conversations and this training has equipped me to lead conversation rather than simply react to them. Thank you!”

Amanda Slaight, Ultimate Software, ERM 


“I thought this was a valuable training not only for our sales personnel but our marketing team and client executives as well. These tools can be used by many in our organization.”

Peter Snell, Infinite Campus, Editor RFP Responses 


“Impactful. Flawlessly executed. The training positioned me to move mountains with my customers.”

VP, Ultimate Software, Executive Relationship Management


Great continuation of the messaging in the Demo2Win series. I will definitely use some of these techniques in driving more meaningful discovery.”

Scott Parker, Icertis, Director Presales 


Virtual Training Options

What makes our virtual training different?

  • Designed with Virtual in Mind –  Most skills-based training companies have implemented virtual training with exhausting lectures and slide-sharing. Not 2Win! We architected and purpose-built our virtual training courses to be flexible, impactful, and practical. Uniquely designed for an online training format.
  • Proven Satisfaction – Our virtual training satisfaction scores are equivalent to our in-person scores. We’re keeping pre-sales, sales, and client success engaged that results in an immediate impact on your team’s effectiveness.
  • Masterful Virtual Delivery and Coaching – No technical difficulties. No sound quality issues. No excuses.
  • Quality Development and Production  – Our lessons and exercises are bite-sized and easy to digest. We use high-quality video, graphics, and activities to create a learning experience that is interesting, challenging, and educational.
  • Grow at Your Own Pace – We scale globally for even the largest enterprises and audiences.
  • A Unique Take on Virtual Training – 2Win! virtual training offers a combination of user-friendly mobile tools, web-enabled video platforms, and virtual coaching so your most expensive resources gain immediate and long-lasting benefit to your strategic goals.


Contact Us


If you have questions about our world-class Winning with Executives Engagement training or would like more information about 2Win! please contact us and we’ll be ready to answer your questions.

The Executive Engagement Workshop