Private 1:1 sessions with experienced insurance and insurtech experts
ITA Monthly Office Hours
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.
How Office Hours Works
Hosted Monthly
Office Hours take place once a month during a dedicated week, typically Monday through Friday.
Multiple Time Slots Available
Each expert offers several 15–20 minute 1:1 sessions across the week to accommodate different schedules
Book Directly
Browse the experts below and book a time that works for you. Sessions are available on a first-come, first-served basis.
Focused Conversations
Founding sponsors supported the InsurTech from the beginning and helped build the InsurTech community
Schedule A Conversation With Experienced Practitioners
Bob Sargent
Founder & CEO, eSpecialty Insurance
Insurance
MGA
Funding
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
Joshua Hollander
CEO of Horton International USA
Leadership Hires
Organizational Structure
Succession Planning
Support to manage head-count growth
15–20 minute 1:1 session
Somil Jain
Principal & Sr. Consulting Actuary
Actuary
MGA
Insurance Product Development
Somil has been practicing in the insurance industry for over 25 years. His experience ranges from some of the biggest names in the industry to helping emerging insurance startups grow profitably. He is a start-up & InsurTech aficionado and has helped multiple MGAs go from 0 to 1. He has helped insurance companies navigate D2C distribution via multiple channels and significantly improve their unit costs. He specializes in helping emerging MGAs and carriers create the best admitted or non-admitted (E&S) insurance products. He can assist you with pricing, competitive analysis, loss ratio and reserving estimates, filings, analytics and getting capacity. For the last few years, Somil has been a judge for InsurTech NY’s Global InsurTech Startup Competition. Somil also serves on the board and as an advisor for multiple insurance and analytics companies.
15–20 minute 1:1 session
John Willemsen
CEO / Founder, Willemsen Advisors
MGA
market entry
organizational scaling
Operational Efficiency
distribution strategy
revenue growth initiatives
John Willemsen is the founder of Willemsen Advisors, a consultancy providing strategic counsel to MGA and Program Administration organizations. He specializes in market entry, organizational scaling, operational efficiency, distribution strategy, talent development, and revenue growth initiatives, guiding clients on positioning, execution, and long‑term alignment. John has advised more than 3,000 MGA/PA business plans across multiple classes and lines of business throughout the MGA/PA lifecycle and has played a key role in launching several insurance companies, including one that went public. His services are sought by those seeking support in launching, scaling operations, receiving strategic advice, or repositioning in the marketplace. John maintains global collaborations with strategic partners, prioritizing transparency, precision, and an in-depth understanding of the sector.
15–20 minute 1:1 session
Frank Sentner
Founder / CEO, Sentwood Consulting
Product design
Product Market Fit
Operations
Operational Efficiency
distribution strategy
revenue growth initiatives
Frank Sentner has built insurance technology solutions for nearly 50 years, working with insurers, agents, and technology providers. In 1984, he co-founded CISCo to create the Sagitta agency management system, which was sold to Vertafore in 1995 and which is still used by some of the largest insurance brokers in the world. He is on the board or advisory board for 9 insurtech startups with some equity stake. His skills lie In product design, product-market fit, and operations for insurtech startups focused on P&C insurance agents and brokers. His only remaining corporate consulting client is ACORD.
15–20 minute 1:1 session
David Gritz
Managing Director, InsurTech NY (Host of MGA Lab)
MGA Launch
Fundraising
Product Development
Marketing
GTM
David is co-founder of InsurTech Fund, a seed-stage VC with 23 portfolio companies, and co-founder of InsurTech NY. InsurTech NY runs the Digital MGA Lab, which has graduated 45 InsurTechs focused on insurance distribution, alongside a growth-stage accelerator with 200+ alumni. David previously co-founded Zero, a behavioral-safety InsurTech acquired by Everest Re. He’s advised startups including TrustLayer, Livegenic, and Pinpoint Predictive, and has spoken at 70+ InsurTech conferences. He holds a J.D. from Mitchell Hamline School of Law and engineering and business degrees from Lehigh University.
15–20 minute 1:1 session
Wendy Boe
Head of Compliance, Turris
compliance
MGA/MGU
Brokers
Agencies
Claims & Fraud
Automation
Operations
Policy and Contract Management
Wendy Boe, CIC, FCLS, CRM, brings more than 25 years of insurance experience across agency ownership, compliance consulting, education, claims/fraud, and insurtech advisory. She has worked with adjusting firms, MGAs, insurtechs, captives, parametric programs, and alternative risk vehicles, giving her a practical view of how insurance products, compliance requirements, and operational realities come together. Today, Wendy serves as a senior compliance leader at Turris Group, where she focuses on insurance compliance automation and helps organizations navigate complex regulatory and risk questions with clarity.
15–20 minute 1:1 session
Jason Wootton
Insurance Executive & Board Advisor
Distribution Strategy
MGA
Partnerships
Data & Analytics
Capacity & Reinsurance
Funding
Jason Wootton is a 25-year insurance industry veteran with experience across carriers, MGAs, and InsurTechs. His background includes direct relationships with hundreds of carriers globally, multiple startup and MGA builds, and firsthand experience visiting thousands of agencies. Jason advises on distribution strategy, data-driven growth, MGA formation, lead generation infrastructure, and partnership development at the intersection of traditional insurance and emerging technology. He has served as a founder and CEO, C-level executive, board member, and senior advisor, bringing both a founder’s mindset and an operator’s instincts to conversations about scaling insurance businesses and navigating carrier, agency, MGA, and InsurTech partnerships.
15–20 minute 1:1 session
Who are Office Hours Designed For?
- 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.
Want to Take Part in Monthly Office Hours?
Monthly Office Hours are part of the broader InsurTech Association experience. Participation is designed for members and non-members who want access to practical perspective, shared learning, and ongoing dialogue across the insurance and InsurTech ecosystem.
If you’re exploring whether ITA membership is the right fit, or want to understand how Monthly Office Hours work in practice, we’re happy to walk you through it.