Our Team

The people behind the paper.

Underwriters, operators, and counsel who have spent their careers in specialty insurance, building the platform they always wished the market had.

Co-Founder

Joshua Rubin CPCU

Josh Rubin is a true cultivator in the insurance world. As Co-Founder of Greenhouse Specialty Insurance Services, LLC, he has spent his career tending to the underwriting landscape with precision, patience, and to deeply understand individual risks. A proud graduate of Virginia Commonwealth University’s Risk Management and Insurance program, Josh also holds the CPCU designation, demonstrating his commitment to mastering the field from root to canopy.

Based in New York, Josh brings a greenhouse mindset to everything he does: fostering growth, nurturing innovation, and creating fertile ground for specialty insurance solutions to flourish. His leadership style is organic and intentional, helping clients and colleagues alike thrive in even the most unpredictable climates. Josh’s goal is to provide those around him with the best possible environment where they can thrive.

Outside of work, Josh’s greatest source of pride is his family. He is a devoted father and beyond family life, he finds balance on the water as an avid boater, in the quiet enjoyment of whiskey collecting, and in exploring the outdoors. These pursuits reflect the same values he brings to his professional life: patience, appreciation, and a steady hand in navigating new horizons.

Co-Founder

Geoff Bernardo CPCU

Geoff Bernardo is a well-rooted figure in the insurance ecosystem, with a career that has grown through dedication, deep expertise, and a genuine passion for sharing knowledge. As Co-Founder of Greenhouse Specialty Insurance Services, LLC, Geoff has helped cultivate a dynamic space for specialty underwriting, particularly in environmental insurance, where his insight helps clients navigate complex risks with clarity and care.

He is a proud graduate of Virginia Commonwealth University’s Risk Management and Insurance program and holds the CPCU designation. Geoff has also contributed to the development of future insurance professionals as a former faculty member at VCU. His approach to risk management is thoughtful, methodical, and always evolving, much like tending a thriving garden. He currently serves on the VCU RMI Advisory Board.

At home in Virginia, Geoff finds his greatest joy in spending time with his wife Mary and their two daughters, Eleanor and Audrey. In his free time, Geoff enjoys coaching and playing ultimate frisbee, reflecting his love for teamwork, strategy, and staying active.

Director of Operations

Heather MacIver CPCU, ACRM, CBIA, INS, AIS

Heather MacIver is the kind of insurance professional who’s deeply rooted in the field. She’s cultivated a thriving career in agency operations and underwriting, growing her skills season after season. Heather is a proud graduate of Virginia Commonwealth University’s Risk Management and Insurance program, and has earned her CPCU designation, both laying the fertile ground for her success. Heather currently serves on the VCU RMI Advisory Board and the Richmond CPCU Society Board.

As the operations lead for the company, Heather keeps everything running like a well-tended garden - streamlining processes, nurturing team growth, and ensuring every branch of the business is thriving. Whether she’s pruning inefficiencies or planting new ideas to improve workflows, she brings a green thumb for strategy and a natural knack for nurturing strong client relationships. She’s the insurance world’s equivalent of a perennial - steadfast, resilient, and always in bloom.

Born and raised in Virginia, Heather has always found joy in the great outdoors. Whether she's cheering from the sidelines of a soccer field or heading for the Blue Ridge Mountains, nature is her happy place. She’s all about road trips, camping weekends, and trail hikes - with her husband and four kids along for the ride.

The wider greenhouse

Growing with us.

Dane DiEugenio

Underwriting & Operations Analyst

Dane DiEugenio is growing his career in the specialty insurance world from the ground up. He found the field almost by accident, taking an elective risk management course at Virginia Commonwealth University out of pure curiosity and enjoying it more than anything else on his schedule. He changed his concentration to follow it, and a summer in the VCU Lester Summer Fellow Program, spent on both the carrier and brokerage sides of the business, helped him settle on underwriting. He returned for his final year as president of his Gamma Iota Sigma chapter while interning with Greenhouse Specialty. That spring, he graduated with the Davis Ratcliffe Risk Management and Insurance Award, recognizing outstanding achievement in the field, and began his full-time career.

As an underwriting and operations analyst, Dane spends his days tending two rows at once, learning the fundamentals of the business, supporting the servicing side, and building internal tools that make the team’s work a little lighter. Whether he is digging into a renewal or planting a new workflow with emerging agentic coding platforms, he tries to leave things better tended than he found them. He is early in his growing season, curious, eager, and reaching for the light.

At home in Virginia, Dane and his fiancée enjoy making the most of the outdoors, whether that means time on the water, adventures in nature, or gathering with friends and family. Those pursuits mirror what he hopes to bring to his work: patience, curiosity, and an appreciation for things that take time to grow.

Matthias J. Kaseorg

General Counsel, Director of Claims

Matthias Kaseorg has cultivated a career rooted in advocacy, problem-solving, and helping clients navigate complex challenges. With a diverse litigation practice spanning employment and commercial matters, Matthias has represented individuals, businesses, government employees, landlords, tenants, and company leaders through a wide range of disputes. His experience in Virginia courts, federal courts, arbitration proceedings, and mediation has helped him develop a thoughtful approach to untangling difficult issues and finding practical paths forward.

Before branching into his current practice, Matthias spent several years as an insurance and commercial defense litigator representing transportation, hospitality, construction, and retail businesses. His work included defending companies facing environmental liability, products liability, premises liability, and motor vehicle accident claims. Matthias also has prior experience with toxic tort and products liability litigation. His collective experience helps him assess a broad range of legal and environmental risks faced by organizations.

As someone who has spent his career examining risk from every angle, Matthias brings a well-rooted perspective, a steady hand, and an appreciation for the value of careful analysis when navigating complex challenges.

Outside of work, Matthias enjoys spending time outdoors with his wife and two children, playing sports, visiting National Parks, exploring new cities, catching Richmond’s outdoor music concerts, and playing guitar for his local church. Whether on the pickleball court, ultimate frisbee field, or supporting Historic Richmond through the organization’s Junior Board, Matthias values community, teamwork, and investing in things that stand the test of time.

Shared roots

VCU

Josh, Geoff, and Heather all came through VCU's Risk Management & Insurance program.

Proud supporters of the VCU RMI program ↗

E&S

Specialty underwriters. Understanding niche risk isn't a specialty we added. It's the reason we exist.

RVA

Headquartered in Richmond, Virginia, the underwriting town where the founders learned the craft.

Join the Greenhouse

Come grow with us.

We’re building a place where good people can thrive, learn, and lead: underwriters, operators, and talent we haven’t thought of yet. If you want to work at Greenhouse, don’t wait for a job posting: apply directly. Send us a short note about who you are and the work you want to do.

Apply directly Read our culture manifesto

Applications go straight to the founders: Josh@GreenhouseSpecialty.com

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