About

About

We Are Hill Country Underwriters

Where Integrity Leads and Expertise Delivers. 

Hill Country Underwriters is a premier provider of casualty insurance based out of Dallas, Texas. HCS’s team brings with it a proven track record of success along with a wealth of experience in assessing and mitigating risks unique to craftspeople and trades professionals with a deep understanding of the nuance and complexities of the evolving landscape of artisan construction.

Forward Thinking

OUR MISSION

Our mission is to be a strategic partner to our clients and the market. Connecting risk with opportunity through smart, ethical, and forward-thinking solutions. We aim to simplify complexity and bring clarity and confidence to every transaction.

our Culture:

Honesty, Strong Work Ethic & Dependability

INNOVATIVE and FLEXIBLE SOLUTIONS

We consistently address market demands with innovative and flexible solutions. By actively managing relationships, we strive to minimize surprises. Instead of reacting to problems after they arise, our focus is on anticipating and preventing them from the outset.

Through its experienced team and deep wholesale relationships, HCS strives to provide the highest level of customer service and satisfaction through a culture of honesty, integrity, dependability, and strong work ethic.

Market-Driven Innovation

Proactive Risk Management

Strategic Relationship Management

Experienced Team

Strong Wholesale Partnerships

Customer-Centric Focus

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Experts in Insurance & Management

The CRIS® designation reflects our specialized knowledge in construction risk. This certification ensures we can provide tailored insurance solutions that address the unique challenges of the construction industry.

David Henry

President

David was born and raised in South Texas and has dedicated his career to serving companies and clients across the insurance industry. He began as an insurance litigation attorney, representing clients in complex property and casualty cases…

David Henry

David was born and raised in South Texas and has dedicated his career to serving companies and clients across the insurance industry. He began as an insurance litigation attorney, representing clients in complex property and casualty cases. That experience gave him a deep understanding of the challenges policyholders and insurers face—not just in the courtroom, but in day-to-day risk management.

With a legal background that offers a unique perspective, David is known for crafting smarter, more effective insurance solutions tailored to real-world exposures and evolving business needs. As President of Hill Country Underwriters, he leads strategy and operations with vision, energy, and a commitment to operational excellence and sustainable growth. 

Before taking on his current role, David led a specialized insurance program where he built and scaled a team that grew the book from approximately $26 million to over $120 million in annual premium. Under his leadership, the program achieved a stronger spread of risk and significantly improved loss performance.

Outside the office, David is a proud Baylor alum (Sic ’Em Bears), husband to his amazing wife Jess, and father to three wonderful children. He’s also an enthusiastic supporter of youth athletics—and most weekends, you’ll find him on the sidelines cheering his kids on.

Matt McDonald

Vice President

Matt was born and raised in Denver, Colorado (Go Broncos) and later moved to Nebraska to continue his education and play football at the collegiate level. After wrapping up his time in Nebraska, he relocated to Texas with his family…

Matt McDonald

Matt was born and raised in Denver, Colorado (Go Broncos) and later moved to Nebraska to continue his education and play football at the collegiate level. After wrapping up his time in Nebraska, he relocated to Texas with his family and began his career in the wholesale insurance industry. He went on to become one of the first hires on a newly restructured underwriting team, where he quickly put his leadership skills to work managing construction-focused teams at both the field and program levels.

Now serving as Vice President of Hill Country Underwriters, Matt leads with integrity, resourcefulness, and a focus on delivering results. With a deep understanding of coverage and a reputation for being a go-to expert in the space, Matt recently led the development of a small business platform aimed at helping his team grow and diversify their book. Since entering the program space, he’s been a driving force behind more than $159 million in gross written premium and helping shape one of the leading programs in the market. 

The insurance industry has given Matt the flexibility to focus on what matters most, spending time with family and friends. He’s passionate about coaching football and loves a good board game night with the family. 

Our Values

Integrity

Our integrity is the foundation of everything we do, ensuring that every policy, recommendation, and service we provide is guided by honesty, transparency, and a deep commitment to protecting what matters most to you.

Resourcefulness

We bring resourcefulness to every challenge, using our deep industry knowledge and innovative solutions to help you navigate insurance with confidence and clarity.

Results

Our proven track record of positive results reflects our commitment to delivering tailored insurance solutions that truly protect and support our clients.

Reach out to Us Today to Get Started

Reach out to us for a consultation

Feel free to reach out to us for expert advice, customized solutions or personalized consultation tailored to your needs.