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About Us

CHSI Technologies is the company behind CHSI Connections®

CHSI Connections® – Accelerate To Great®

Our mission is to level the playing field for small and mid-market companies by providing access to the highest quality insurance technology solutions at the most affordable investment price in the marketplace.


Our vision is to be the leader in Hosted Insurance Management Solutions. The name CHSI was chosen to communicate the company’s passion, spirit, and values for which it stands: Commitment, Honesty, Service and Innovation.

Game-Changing Insurance Software

With a full-time engineering staff and dedicated partner services team, CHSI is disrupting and redefining insurance technology. We strive to optimize your insurance stack of operations by leveraging our innovations.

CHSI Team And Culture

We are as proud of our people as we are of our insurance technology. The CHSI team is passionate about creating something extraordinary. Our commitment to your success makes us a trusted technology partner for all.

We Are Insurance Experts

CHSI Technologies, the company that makes the CHSI Connections® software, is comprised of inventive and ground-breaking experts who are passionate about creating customer technology that builds trust and inspires loyalty. We value ourselves as the leader in Hosted Insurance Management Solutions, and our team is committed to tackling complex problems by delivering innovative hosted insurance technology solutions to those businesses who need it most. Our success is attributed to the ability to identify underserved markets, deploy our technology, and provide disruptive strategies that offer true value to the clients we serve.

  • Workers' Compensation

  • Self Insured Groups

  • Captives & Risk Retention Groups

  • P & C Carriers

  • Public Entities


Our Leadership Team


Jim Leftwich

Jim is the founder and CEO of CHSI Technologies and has more than 30 years of leadership experience in risk management and insurance.

Lee Mashore

Lee oversees the product development of CHSI Connections®. He has over 20 years of technology and insurance experience in delivering award winning software solutions to the insurance industry.

Richard Mathis

As the leader of the Development Team, Richard brings “tech” to CHSI Technologies. He has over 20 years of experience building and delivering web-based application software.

Trevor Lightbound

VP of Partner Services
Trevor works directly with clients and ensures their success with CHSI Connections®. His unique combination of leadership, insurance management and technical skills make him a valued resource on each project.