Training for Executive Sales Conversations

Confidence and competence. All too often, that’s what’s missing when sellers meet with C-level decisionmakers. But with the right training, your sales reps can frame value in terms that matter to senior executives, leading to smarter proposals, faster closes, and fewer stuck deals.

Photograph of waterfall representing powerful effects of executive decisions in sales

Most Sellers Have a Fear of Heights

When it’s time to engage senior executives, many sellers lose their footing.
They default to product talk. They over-index on what your solution does. And they miss the connection to strategic priorities and financial outcomes.
 

This “fear of heights” leads to stalled deals, missed opportunities to communicate your solution’s full value, and decisions that drag on and on—or never come at all.

A diagram showing what it takes to sell to executive-level decision-makers: compelling stories, quantify impact, and build urgency

What Sellers Need to Earn Executive Credibility

Executive buyers don’t want a rundown of product features—they expect conversations that speak to their business priorities. 

To win with executive buyers, your reps need to: 

  • Tell compelling stories that connect your value to key business initiatives
  • Quantify impact with credible ROI and performance metrics
  • Build urgency and construct investment-ready business cases

Skills Training for Executive-Level Conversations

When your sellers learn to close the gap between product knowledge and business value, they can engage executive buyers with confidence, justify the decision, and drive the urgency to act now.

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Engage Executive Buyers with Confidence

Turn high-stakes meetings into high-leverage moments.

Gain access and earn credibility with senior decision-makers

Shift from tactical conversations to strategic business dialogue

Ask smarter questions that uncover executive-level priorities

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Tell a More Strategic Story

Connect your solution to what matters most to the business.

Frame your message around boardroom business goals

Use financial storytelling to justify the decision

Create urgency using executive buyer psychology

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Build a Convincing Business Case

Help executives make—and defend—the decision to buy.

Quantify value with credible ROI and performance metrics

Craft investment-ready business cases that pass the CFO test

Strengthen consensus by aligning with cross-functional concerns

Recognized for Excellence

Win the C-Suite

Most training leaves sellers stuck at the mid-level—unable to gain access or justify value at the executive table. 

Give your reps the confidence, language, and urgency to earn the trust (and budget) of executive buyers. 

Let’s turn high-stakes meetings into signed deals.

Training That Sticks

Live and Virtual Workshops
Sales training expert leads an on-site workshop for a B2B sales team

Your team will engage in high-impact sessions—virtual or in person—where they’ll apply concepts to real deals, practice key moments, and get expert coaching in the room.

Self-Paced Learning and AI Practice
Screenshot of Tim Riesterer as an instructor in a virtual sales training event

Your reps will sharpen their business fluency through guided digital modules and AI-powered simulations they can complete in the flow of work—without disrupting selling time.

Ongoing Reinforcement Tools
AI-powered coaching platform with AI coach giving sales rep feedback in practice session

After training, your team will continue to build confidence using an on-demand content library, role-play rubrics, and conversation planners designed to support deal-by-deal coaching.

See the Impact

“Our CxO consultant helped us distill a complex proposal down to a few thematic value drivers with particular focus on business impact vs. solution features. With our consultant’s help, we focused on the monthly cost of ‘not now,’ which helped our client expedite the decision we wanted.”
Enterprise Account Executive, global cloud service and software provider

Sharpen Your Strategy with These Expert Resources

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Common Questions About This Training

A: Any seller who needs to earn access to senior executives, speak the language of business, and create urgency to act. This includes mid-to-senior reps working complex or enterprise deals, as well as front-line managers and enablement leaders who support those conversations.

A: Traditional programs stop at benefits. This training goes further—teaching your reps how to link your solution to high-priority business goals, justify the investment with financial credibility, and construct compelling stories grounded in executive psychology. It drives a more compelling, urgent business case.

A: Your team will be equipped to spark business curiosity, earn time with the C-suite, and lead strategic conversations that justify action. We use science-backed frameworks to help reps answer the two questions every executive is asking: Why should I spend money on this? Why should I do it now?

A: Yes, because they’ll apply the skills to real opportunities during training. And they’ll keep practicing with tools designed for daily use, including AI-powered simulations, role-play rubrics, and conversation planners built for every stage of the deal.

A: You’ll see the difference in the conversations your reps are having—more access, stronger financial cases, and faster decisions. We provide tools to help managers track progress, plus challenge rubrics and reinforcement resources that tie directly to deal outcomes.

Round Out Your Sellers’ Skills

Executive selling is just one part of your team’s performance puzzle. Explore additional training programs designed to win every commercial conversation.

Get a Training Plan Built for Today’s Buyers

Let’s match the right training options to your team’s goals.