Bob is a Founding Partner and lead investor at 42Chat, which uses AI conversations over text to solve business problems. 42Chat provides solutions to healthcare, education, professional and amateur sports, and event industries and is one of the fastest-growing companies in the AI chatbot space.

Prior to 42Chat, Bob built and sold G2 Web Services (risk mitigation in the payments industry) and ConnexionPoint (health care insurance life cycle management) to Verisk Analytics and Integrity Marketing Group, respectively.

He and his wife Lisa have 4 children and split time between their homes in Sarasota, FL and Draper, UT.  The Caldwell’s are proud of their philanthropic work through The Caldwell Family Foundation (a 501c3 focused on providing food, support, and innovative educational programs to at risk kids).

The Power of Successful Engagements

Wednesday, February 25, 9:20 AM – 10:00 AM
TRACK 1

This session introduces the concept of Successful Engagements — any meaningful interaction between your organization and its audience. These include questions asked and answered, messages delivered and read, and any desired user action, such as clicks, purchases, or completed processes. When companies begin tracking Successful Engagements across all channels — web, phone, app, SMS, social, and more — they gain clearer insight into which channels truly drive ROI. As industry demographics shift and the workforce continues to grow younger, understanding these engagement patterns becomes increasingly important. Organizations can tailor their communication strategies to the channels that resonate most with each audience segment, leading to stronger outcomes and more effective engagement overall.