Winning Customer Engagement: Highlights from Mediafly’s Chicago Roundtable

By Mediafly | October 28, 2025

Chicago, IL — October 22, 2025

Hosted in partnership with Acquia, Mediafly’s Winning Customer Engagement event brought together revenue, marketing, and customer success leaders to explore a single, pressing question: How do modern organizations win at their customers’ “moment of truth”?

Setting the Stage

Opening the evening, Tony Kavadas, Chief Sales Officer at Mediafly, welcomed guests with a reflection on how the buyer journey has changed.

“The moment of truth comes faster than ever,” Tony noted, “and it’s shaped by every single interaction leading up to it.”

Joined by Mike Dabisch, Senior Director of Commercial Applications at Constellation Brands (CBI), and Paige Aleski, Senior Digital Strategy Value Manager at Workday, the panel explored what winning customer engagement looks like when outcomes—not outputs—define success.

The “Moment of Truth” in Action

The discussion began by defining how that moment shows up across industries. For large CPG manufacturers such as CBI, the challenge lies in selling directly to distributors while helping them drive sell-through into retail accounts. Their teams need access to the right tools at the right time—particularly localized, brand-compliant content—making governance critical.

In contrast, B2B SaaS organizations face multiple “moments of truth” throughout the buyer journey. For Workday, success means embedding value from the very first conversation instead of leading with features and functions. Its value-selling framework maps content and insights to every stage—from early discovery through to closing—ensuring each interaction reinforces what customers care about most.

Measurement Is Everything

At Constellation Brands, Mediafly helps commercial teams prepare for every customer conversation with data-backed insights that lead to faster, more confident buying decisions. The platform’s deep intelligence capabilities enable complex, distributed teams to tie every seller’s activity—direct or indirect—to business-critical KPIs.

Enterprise software sales bring a different kind of complexity, with larger buying committees and longer cycles. At Workday, anticipating customer needs before meetings begin has become essential. Anchored to metrics such as win rates and deal progression, GTM leaders there focus on sellers’ adoption and usage of content and value-selling tools. This approach connects value management directly to customer strategy, empowering teams to move beyond feature selling toward measurable business impact.

From Content to Confidence: Driving Deeper Engagement

The conversation naturally evolved to how content amplifies customer confidence and drives measurable ROI. Both organizations emphasized that value-driven content is only effective when used intentionally—by the right person, at the right stage, for the right customer challenge.

By leveraging Mediafly’s engagement analytics, teams at both companies learn which stories resonate most and how they influence deal progression. Together, these examples showed how Mediafly enables organizations to connect content performance with business outcomes, transforming engagement into a measurable advantage.

Turning Every Interaction into Measurable ROI

The session closed on a pragmatic note: proving ROI starts with empathy. Workday approaches measurement as an ongoing dialogue with sellers—tracking where they’re winning, what’s changing, and whether those on the front lines see improvement. Constellation Brands focuses on real sales behavior, using those insights to guide enablement priorities and celebrate tangible wins.

When reflecting on lessons learned, both organizations agreed that simplicity drives adoption. After moving from legacy systems to Mediafly, Constellation Brands experienced a smoother deployment. Workday, which went live within weeks of implementation, found that simplifying rather than over-engineering processes led to the best outcomes. Both perspectives reinforced a consistent takeaway across the room: value realization doesn’t come from doing more—it comes from doing what matters, better.

Looking Ahead: Embrace Value and Reduce Enablement Complexity

As the evening continued inside the museum’s halls, conversations carried on—proof that when organizations speak the language of customer value, the dialogue doesn’t end when the session does. Across industries, revenue leaders share the same goals: consistent, value-driven sales motions, continuous training, and visibility into performance metrics.

Mediafly believes in the power of a unified, configurable sales enablement platform that captures buyer insights, pain points, objectives, and outcomes—combining seller readiness, business cases, content delivery, and performance intelligence within CRM workflows.

With brand-aligned content, scalable onboarding and coaching, and real-time performance insights, Mediafly gives revenue organizations the clarity, confidence, and tools to turn every buyer interaction into measurable business value.

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