Rich Dooley | Digital Insurance Summit

Digital Insurance Summit 2026

May 18 - 19, 2026

Westin Copley Place - Boston, MA

Rich Dooley

Rich Dooley

Vice President, Product Commercialization The Clearing House

Transforming Modern Insurance Models with Data and AI

3:20 PM Track B: Fireside Chat: The Right Kind of Friction: Balancing Fraud Prevention and Digital Experience in Insurance

Most carriers treat fraud prevention and customer experience as competing priorities. Build too many controls and you slow down legitimate customers. Strip them away and you leave the door open. The carriers pulling ahead have figured out it doesn't have to be a tradeoff. In this fireside chat, leaders from Plaid and The Clearing House get specific about where that balance lives: how digital payments reduce fraud exposure at both premium collection and claims payout, why the verification moment matters more than most carriers realize, and what it actually looks like to build an infrastructure that protects against bad actors without adding friction for good ones. Attendees will walk away with:

• How digital payments close fraud windows that checks and manual processes leave open

• Why premium collection is an underrated fraud prevention touchpoint

• What carriers getting this right are doing differently at FNOL and claims payout

• How to make verification faster for legitimate customers, not just harder for fraudsters


Innovation for Efficiency: Streamlining Insurance Experiences and Operations

2:20 PM Panel: Eliminating Payment Pain Points for Customers, Agents & Service Teams

For many customers, a confusing bill, a failed transaction, delayed posting, or a lack of flexible payment options, friction at checkout can instantly undo otherwise strong CX. For agents and service teams, broken payment workflows create unnecessary calls, escalations, and manual work that slow everything down. In this panel, carrier and agency leaders and Insurtech partners unpack how they are redesigning payment experiences to feel fast, transparent, and effortless for all parties. Walk away with insights on how to:

  • Eliminate common payment breakdowns that drive customer complaints and service volume
  • Design payment journeys that feel seamless across digital, agent-assisted, and call center channels
  • Reduce friction for agents and service teams while increasing speed and accuracy
  • Use payments as a strategic touchpoint to strengthen trust, retention, and overall CX

Check out the incredible speaker line-up to see who will be joining Rich.

Download The Latest Agenda