Hearst brings AI-driven revenue strategy to the Lead-to-Cash Bash

Deals using AI are closing about 15 days faster, and we’re winning a third of those opportunities compared to one quarter without AI.”

Michael McCarthy, Senior Director of AI, Sales and Business Solutions at Hearst

When Michael McCarthy, Senior Director of AI, Sales and Business Solutions at Hearst, took the stage at the Lead-to-Cash Bash, the conversation quickly moved beyond buzzwords.

At one of the largest media organizations in the country, McCarthy operates where strategy meets execution — inside the revenue engine itself. His focus is not abstract AI theory. It’s operational impact: accelerating deal cycles, improving win rates and increasing average deal size through disciplined systems and AI-powered sales enablement.

At Hearst, that transformation starts with structure. Managing technology and revenue operations across dozens of properties requires careful resource allocation and standardization. “We need to balance incoming requests carefully against available resources,” he explained, describing Hearst’s internal evaluation framework that forces qualitative and quantitative review before projects move forward.

That discipline laid the groundwork for modernization — particularly in advertising revenue systems. Hearst is roughly two-thirds through standardizing its advertising technology stack, beginning with insertion order systems and product alignment. But the next frontier, McCarthy emphasized, is AI-driven lead-to-close optimization.

And the results are already measurable.

Deals supported by AI tools are closing an average of 15 days faster. AI-assisted opportunities are winning at higher rates — roughly one-third compared to one-quarter without AI support. New business deal sizes have climbed dramatically. High-adoption reps are outperforming peers with outsized book-of-business growth.

These outcomes are driven by purpose-built GPT tools embedded directly into sales workflows — from industry prospecting analyzers and sales prep accelerators to cold-call simulators, proposal builders and creative auditing systems. Rather than experimenting at the margins, Hearst has integrated AI into daily revenue operations.

For smaller publishers watching from afar, McCarthy offered practical advice: identify an AI champion outside of IT, connect directly with OpenAI, invest in prompt engineering training and begin building focused agents aligned to revenue goals. Start operational. Start measurable.

It’s exactly this practitioner-driven perspective that makes the Lead-to-Cash Bash different.

Held November 12–14, 2025, at the Walt Disney World Swan & Dolphin Resort and Conference Center, the event brings together executives responsible for revenue, sales operations, ad fulfillment, production and finance systems. Now in its sixth year, the Lead-to-Cash Bash has become a niche gathering focused specifically on the technology, workflows and models that power modern revenue operations.

Unlike broad industry conferences, the Bash centers on real systems, real case studies and peer-to-peer exchange among operators facing similar challenges. As McCarthy noted during his appearance, the value comes from “practical do-ers” sharing actionable insights — not abstract strategy.

For media organizations grappling with CRM modernization, billing system alignment, marketing automation, AI sales enablement or cross-property standardization, the Lead-to-Cash Bash offers concentrated, implementation-focused dialogue.

Because transformation doesn’t happen from inspiration alone. It happens through systems, discipline and shared operational intelligence.

And increasingly, leaders like Michael McCarthy are proving that AI — when embedded thoughtfully inside revenue workflows — is no longer experimental. It’s a competitive advantage.