November 12th, 2025 - November 14th, 2025

Meet Us at Lead to Cash Bash

Meet Us at Lead to Cash Bash

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Upland Second Street Session

Monetizing the Moment: How Gannett and Federated Media Built Million-Dollar Promotions Businesses

In today’s fast-moving media landscape, growth belongs to those who can monetize the moment. Every organization is chasing sustainable revenue, but few have mastered how to replicate success year after year.

Join two powerhouse media leaders, Rebecca Capparelli, Vice President of Promotions at Gannett / USA TODAY Network, and Deb Williams, General Manager of Digital Sales at Federated Media, for an inside look at how they’ve each turned promotions into proven, scalable revenue machines.

At Gannett, Rebecca’s team has engineered a $30M+ annual promotions business through a finely tuned mix of people, process, and technology on a national scale. And at Federated Media, Deb led a local-first initiative that trained sellers to make promotions a true client solution—driving seven-figure revenue growth and 80% team adoption.

In this session, you’ll learn how to:

  • Empower your people: Build and train teams that drive creativity, accountability, and consistent results.
  • Operationalize your process: Create repeatable playbooks that scale from local to enterprise.
  • Maximize your technology: Use the right platforms to transform bold ideas into measurable client wins.

Whether you’re leading a national media group or a local team, you’ll walk away from this session with a practical framework to build your own revenue machine—turning short-term wins into sustainable growth.

Moderated by Julie Foley, Senior Customer Success Manager at Upland Second Street along with Rebecca Capparelli, Vice President of Promotions at Gannett / USA Today Network and Deb Williams, General Manager of Digital Sales at Federated Media.

Session Speakers

Session Speakers

Rebecca Caparelli, Gannett
Rebecca Caparelli, Gannett
Vice President of Promotions
Vice President of Promotions
Deb Williams, Federated Media
Deb Williams, Federated Media
General Manager of Digital Sales
General Manager of Digital Sales
Julie Foley Speaker
Julie Foley
Julie Foley
Senior Customer Success Manager
Senior Customer Success Manager

Connect with Julie

Connect with our Expert

Connect with our Expert

Tom McLaughlin speaker
Tom McLaughlin
Tom McLaughlin
Account Executive
Account Executive

Connect with Tom

About Indigo Trigger's Lead-to-Cash Bash 5

The Lead-to-Cash Bash is a two-day niche event focused on Lead-to-Cash technology, strategies, and success stories. We’ll be taking over the Walt Disney World Swan Resort for two days of sessions focused on the tools and models that drive revenue operations and sales enablement at some of the world’s largest media companies.

Indigo Lead-to-Cash Bash 5
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Who Should Attend?

  • Any Executive Responsible for Driving Revenue and Effective Sales Operations within Newspaper, Broadcast, and B2B media Groups.
  • Sales Reps & Revenue Managers
  • Sales & Sales Operations Professionals
  • Production & Ad Fulfillment Experts
  • Finance Ops Professionals
  • Lead to Cash System Administrators (CRM’s, OMS’s, Production & Creative Platforms, Reporting Platforms, Billing Systems)

Don't miss your opportunity to monetize the moment