Skip to main content


  • Headquarters: Illinois, USA
  • Acquisition Date: November 2019
  • Vertical Market: Insurance & Benefits Administration


Founded in 1993 as the carrier division of Applied Systems, Insuresoft has been delivering core policy, billing and claims administration software for Property & Casualty (P&C) insurers of all sizes for over 25 years. Their flagship product, the Diamond System, is an enterprise software solution used by both personal and commercial lines insurers. Today, over 50 P&C insurers ranging from start-up managing general agents to some of the largest carriers and brokers on the planet trust Insuresoft and the Diamond System.

We were looking for a partner that enabled us to more effectively compete against some of our larger competitors, that had a strong understanding of the insurance industry, and that would allow us to operate independently while simultaneously benefitting from the scale across the portfolio.

— Tony Villa, CEO, Insuresoft

The Decision to Sell

Insuresoft was contacted by the Volaris team in 2019 and had ongoing meaningful discussions about acquiring it, as well as Insuresoft’s wholly owned subsidiary companies: Covenir (business process outsourcing), Red Hawk (systems integration) and Kaboodle (data analytics and partner ecosystem). Together, these four companies were able to present a full solution to insurers for both software and services.

Insuresoft was looking to further expand on its success and recognized that more growth capital would be needed. The leadership team identified three key traits they sought in an acquirer: stability, insurance industry knowledge and the ability to maintain their brand and identity post-transaction. Volaris proved to be the best fit as an acquirer.

Volaris provided stability and scale for Insuresoft, as an operating group within Constellation Software. Further, it had a strong understanding of the insurance industry, as demonstrated by their current portfolio assets within the broader insurance vertical. Finally, Volaris’ decentralized model allowed all four companies to retain their brand, culture and independence, while also benefitting from being part of an even bigger team.

The ability to network with other software vendors in our space and share best practices, has energized our people and enabled us to better serve our clients.

— Terry Brown, General Manager, Insuresoft

Post-Acquisition Success

Since joining Volaris in late 2019, Insuresoft is just beginning to leverage the network of like-minded leaders and team members across the Volaris organization. Insuresoft team members have expressed excitement over the acquisition, particularly due to the amount of personal development and career growth opportunities now available. Moreover, the clients are equally excited about the continued high levels of service being delivered by the same team members they’ve grown to know and trust.

Insuresoft, as well as Covenir, Red Hawk and Kaboodle, are continuing to grow their respective client base through cross-selling initiatives across the broader Insurance & Benefits portfolio companies. These organic growth goals are also being supplemented through targeted acquisition plans that will extend the current product and service capabilities while simultaneously growing market share.