John D. Dempsey
Co-Founder and Executive Chairman
John brings years of experience within the risk management and insurance spaces as founder of Dempsey Partners, the Global Director of Aon’s Claims Preparation, Advocacy and Valuation team, and partner at Terrabella Risk Consulting LLC. John pioneered policyholder-oriented complex claims services that led to the resolution of over $14 billion in losses.
Chad Hollingsworth
Co-Founder and Chief Executive Officer
Chad was a co-founder of Triax Technologies Inc., where he was part of the team that created Spot-r®, an IoT platform focused on optimizing worker performance. He also served as principal of On Target Consulting LLC, where he served construction technology companies with channel partnerships and go-to-market strategies including insurance. Chad is a recognized industry leader in IoT and SaaS solutions.
Bret Bush
Co-Founder and Executive Vice President
Bret is a 30-year veteran in construction and insurance, leveraging IoT to drive innovation across the risk management landscape. Bret was the Strategy and Execution Lead of IoT at The Hartford, leading successful large-scale IoT deployments on projects up to $500 million. His strategies have changed how stakeholders operate through the deployment of sensor technology, data analytics, and business intelligence tools.
Lisa Behning
Senior Vice President of Marketing & Business Operations
Lisa specializes in driving brand growth, operational excellence, and go-to-market strategies. With 20+ years’ experience in both agency and in-house leadership roles spanning construction, health insurance, telematics, and SaaS, she has been the driving force behind double-digit company growth, operational effectiveness, and achieving maximum ROI.
Matt Joyal
Vice President of Technology
Matt is a leader in IoT technology product development and business strategy. As the former Chief Technology Officer of Pillar, Matt created their product roadmap and was instrumental in building Pillar’s development team through clear communication processes. Matt worked closely with myriad contractors, owners, insurers, and technology professionals to deliver industry-leading IoT solutions and services.
Jon Taylor
Customer Success Manager
Jon has built his 25+ year career around delivering exceptional client experiences, ensuring projects are delivered on time, on budget, and with client satisfaction. He has managed large-scale construction buildouts and technology deployments for Fortune 100 companies. At Insight Risk, Jon oversees technology deployments and guides clients seamlessly through every stage of their project life cycle.
Zach Siegel
Customer Success Manager
Zach brings nearly a decade of experience in project management and customer success, supporting clients across property management and workplace environments at companies like WeWork and URBY. Zach supports clients throughout the full technology deployment process, ensuring smooth coordination before, during, and after installation while helping teams respond quickly to alerts and evolving project needs.
Justin Faust
Chief Financial Officer
Justin founded Bushido Strategic Advisory to provide strategic and financial consulting services to professionals throughout the insurance ecosystem. Prior to Bushido, Justin served as EVP of Finance and Mergers & Acquisitions for EPIC Insurance Brokers. Justin joined EPIC as part of ESPI’s late 2017 investment in Paragon Insurance Holdings, a specialty MGA where he served as CFO.
Michael Reich
Chief Underwriting Officer
Mike joined Insight Risk from Berkshire Hathaway Specialty Insurance, where he successfully managed a nationwide Builder’s Risk portfolio with a specific focus on large value catastrophe-exposed accounts. Prior to joining Berkshire Hathaway, Mike led the northeast region of Hiscox, Inc.’s construction property group. He is the former Chair of the Inland Marine Underwriting Association’s Construction Committee.
Victor Nieznalski
Vice President, Builder's Risk
Victor joined Insight Risk with over a decade of commercial insurance experience, having primarily concentrated on underwriting complex, technical North American construction property placements for international carriers such as AXA XL and Berkshire Hathaway Specialty Insurance. He holds IIC Chartered Insurance Professional (CIP), RIMS Canadian Risk Management (CRM), and IRMI Construction Risk and Insurance Specialist (CRIS) designations.
Alyssa Landy
Assistant Vice President, Builder's Risk
Alyssa joined Insight Risk with nearly a decade of Builder’s Risk underwriting experience, having worked with leading carriers including Chubb and Zurich North America. Throughout her career, she has written policies for some of the largest names in construction and is recognized for her strong sales acumen, customer service, and time management skills. Based in the greater New York City area, she expands Insight Risk’s growing East Coast presence.
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Whether you’re a contractor, developer, risk manager, broker, or carrier, reach out to discuss how we can work together to reduce losses and keep job sites moving.
