reThought Leadership Team

reThought Flood is a new kind of insurer. We’ve deployed our enormous risk modeling expertise to develop a unique, technology-based approach to underwriting flood insurance. Our advanced data analytics create the understanding necessary to build a sustainable private US flood
insurance market.


Cory Isaacson

Chief Executive Officer

Cory Isaacson is CEO of reThought Insurance Corporation, which he leads from his home and reThought HQ in Denver, Colorado. He’s spent more than a quarter century in the tech business, and ten years in insurance technology, including a stint as CTO at RMS. A tireless entrepreneur and a ceaseless innovator, Cory spends his days leading and supporting the reThought team, and for the moment spearheading the MGA’s technology development in his role as acting CTO. He has five patents to his name.

Cory says flood insurance is: “a vital product that needs to get out to market, because everyone is at risk. Everything I can do, and we as the reThought team can do, to bring flood insurance to more homes and enterprises will help build resilience and make every business and family better prepared for the changing future.”

Colleagues will be surprised Cory calls anything “spare time,” but outside reThought he’s working on a personal engineering projects to develop newfangled decorative lighting. 


James Rice


James Rice is President of reThought Specialty, and has worked in insurance and catastrophe modeling his entire career. He is also President of reThought Specialty, where he brings four decades of experience in niche brokerage and MGAs, including 15 in insurTech, to his role overseeing his team’s highly complex risk placement work. Jim’s kept interested by the sector’s ever-evolving technologies, such as reThought’s bespoke flood underwriting technology platform. He says balancing the satisfaction of his own intellectual curiosity and the application of his knowledge to all those reliant on him is both his biggest challenge and greatest reward.

Jim describes flood insurance as a “last frontier,” and says reThought helps the industry manage risk better. “We’re closing the protection gap, reducing costs, and increasing customer satisfaction. We’re also helping insurers to understand and meet policyholders’ needs better through innovative technologies.”

When he’s not thinking about flood risk, Jim’s an independent film critic focused on foreign dramas, and participates as a jurist in many independent film festivals nation-wide.  


Derek (2)

Derek Lynch

Chief Underwriting Officer

Derek Lynch is reThought Flood’s Chief Underwriting Officer, with responsibility for development and delivery of products that sustainably close the flood protection gap. With 15 years of insurance-sector experience, Derek now has ultimate responsibility for providing the tools and products that will shift floods from tragedy to inconvenience, and for educating the insurance industry and property owners about flood risk and coverage. That last part is his driving force: unlike most of us, who got into insurance only because it was the best option available at the time, Derek chose the industry so that he could help people in times of need.

“We live in a new world,” Derek says. “Flood exposure is changing everywhere, prediction tools are evolving, insurance coverage is shifting, and so is our ability to implement physical mitigations efficiently. We may be the only insurers trying to solve the underlying issues, and we have the expertise to actually make it work.” 

Derek toils tirelessly to solve all the world’s problems from his home office in Richmond, Virginia, with his dog Chloe, asking about everything: “is there a better way to do it?”


Catherine Myers

Chief Operating Officer

Catherine Myers, reThought Flood’s Chief Operating Officer, has worked in technology for nearly 30 years. She brings enormous leadership experience to her role driving reThought’s technical progress, and overseeing high-level management of operational areas including sales, marketing, and HR. Her overall goal is to ensure corporate strategy is implemented efficiently, and her specialty is driving teams and projects to succeed. That’s something she does with aplomb, from a standing desk wherever she’s working (currently Minneapolis, but soon a farm in Santa Cruz). The job matches Catherine’s preference to work behind scenes to get stuff done, and to help people organize for success around a common goal.

Catherine admits she knew nothing of flood insurance before joining reThought, but now sees the importance of protection with every passing week and storm. “The town I visit for groceries was underwater during the storms in California this winter,” she recalls. “The risk is real, and close.”

Her real passion (aside from flood insurance, of course) is growing the food she uses to cook creative, outstanding family meals.



Sean O'Neill

Director - Programs

Sean O'Neill is Director – Programs at reThought. After a childhood apprenticeship at his family’s insurance agency, he spent years working as a commercial-lines underwriter. He’s exceptional at underwriting catastrophe-exposed property, and enviably skilled at managing relationships and delivering service. He’s in charge of underwriting and distribution under reThought’s successful Residential and Commercial delegated authority programs, which he handles from his home office in Philly. And he’s perfect for his task of liaison with our insurer-partners, because he’s sold on how reThought blends technology and underwriting into one powerful tool to analyze risk at a very granular level.

“Most of my career, flood was rarely talked about by brokers and carriers,” he says, “but now it’s widely discussed. The tricky part is to educate people about their potential exposure, even outside flood zones, but we’re making progress. More and more people realize that basically anywhere in the country could flood.”

Sean enjoys “adrenaline activities.” He once braved the Running of the Bulls, which was “probably not the smartest thing, but will go down as one of the funnest.”.


Joe Simmons

Underwriting Manager

Joe Simmons is reThought’s Underwriting Manager for Residential Flood. He’s spent his entire career so far with reThought, where he began as an intern, then created an internship program to introduce insurTechs and MGAs to college students as an exciting career path. Daily he helps people to protect themselves – and brokers to protect their clients – from flood disasters. Joe looks always to deploy insurance capacity in a sustainable manner, supported by reThought’s sophisticated flood insurance underwriting technology and methodology. He focuses daily from his office in Philly on crafting underwriting solutions, steering projects to satisfactory completion, and building relationships with reThought’s broker-partners.

Joe says flood insurance is critical to the nation’s positive passage through challenging times. “It will allow our country to move forward sustainably through the challenges that extreme weather presents,” he says. “I am proud to be a part of an organization that is doing its part to help resolve this issue.” 

Joe’s always been interested in cartography. “Underwriting flood allows me to study maps, which I truly enjoy,” he says. “I’ve explored all over the U.S. from a virtual bird’s eye perspective.”



Alyse Aquino

Accounting Manager

Alyse Aquino is reThought’s Accounting Manager. From her home in Marion, Illinois, she manages the money, the spreadsheets, and the financial statements, which makes her critical to reThought’s smooth operation. Her specialty, she says, is finding discrepancies – and she’s very good at it. Alyse holds a Masters degree in accountancy, and she passed all four CPA exams on the first try. She’s a huge asset to reThought, since she isn’t an insurance or technology lifer, like the rest of us. She brings unique perspectives from her earlier career roles in child development and university admissions.

Alyse says it’s great that flood insurance is offered, because people need it – but she doesn’t. “I live on the third floor, in an area where not much flooding happens…” she says. She didn’t need it in her previous, pre-flood-insurance life, either, working as a Community Youth Development Volunteer for the Peace Corps. She lived for two years in a yurt in the Gobi Desert with no running water, so even lower flood risk.

When she’s not working with numbers, Alyse is with words. She loves books, reading, thinking about reading, reading about books, and discussing what she’s reading.


Amit Rai

VP of reThought International

Amit Rai is VP of reThought India and reThought Estonia. He founded the data analysis insurTech CyberBoxer, acquired by reThought in 2023, after spending more than six years with risk modeler RMS, where he became a modeling thought-leader. He has since been determined to lever data and AI to build tools that yield the unparalleled understanding necessary to navigate the greatest risk challenges – like flood. From his HQ in Tallinn, Estonia, Amit leads a multinational team to drive innovation in data analytics. He says the end goal must always be a useful application that genuinely benefits insurers and their customers – not just techies. 

Amit perceives an expanding necessity for flood insurance world-wide, because nowhere is safe anymore. “Global warming and precipitation-based flooding are already intensifying flood risk for businesses and homeowners,” he says. “Flood insurance brings protection against costly damages, but more importantly, it gives people peace of mind.”

Amit effectively combines conflicting introvert/extrovert personas. The latter is a highly effective team leader, but his introvert self is an avid reader of philosophy.