Private 1:1 sessions with experienced insurance and insurtech experts
Each month, ITA hosts Office Hours over the course of one week, offering focused one-on-one conversations with operators, advisors, and service providers from across the insurance ecosystem. These sessions are designed to help you get direct answers, pressure-test ideas, and move forward with confidence.
View This Month’s Experts
Office Hours take place once a month during a dedicated week, typically Monday through Friday.
Each expert offers several 15–20 minute 1:1 sessions across the week to accommodate different schedules
Browse the experts below and book a time that works for you. Sessions are available on a first-come, first-served basis.
These are working sessions — come prepared with specific questions or challenges to get the most value.
Bob Sargent has years of experience as an underwriter and broker addressing challenging, unique, or complex exposures. He is also a prior founder with multiple exits and an early-stage investor in innovative insurance organizations. Leveraging this extensive background, he leads his team in enhancing client outcomes through a blend of expertise and technology innovation.
15–20 minute 1:1 session
Josh is an experienced CEO and entrepreneur with a successful track record in executive search and leadership. He specializes in Board placement, C-suite recruitment, and talent strategy for public, closely held and PE and VC-backed companies in sectors including FinTech/InsurTech, B2B SaaS, Financial Services, Insurance and Industry 4.0. Throughout his career, Josh has been a strong advocate for innovation, leadership, corporate resiliency, and digital transformation. He is committed to developing customized business models and implementing creative solutions to drive top-line growth, increase profitability, and improve the client experience.
15–20 minute 1:1 session
Insurtech founders and operators
Insurance professionals evaluating new tools or approaches
Teams navigating growth, regulation, or distribution challenges
Anyone looking for practical, experience-based guidance
These sessions are best suited for specific questions and real business challenges.
