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Roxie I.T.

Roxie I.T. is a Lexington, Kentucky managed IT services provider offering outsourced IT management, IT optimization and virtual CIO services to small businesses.

Last updated September 27, 2026

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Overview

Roxie I.T. is a managed service provider (MSP) based in Lexington, Kentucky, that delivers outsourced IT support and technology management to small businesses. The company positions itself as a full-ownership IT partner: rather than acting as a break-fix vendor, it takes over day-to-day IT operations, anticipates and responds to IT scenarios, and manages hardware, software, cloud services, central business systems, VoIP phone systems and technology strategy on behalf of its clients. Its stated value proposition is quick, affordable support that protects the bottom line by reducing cost and downtime. The firm organizes its work around two main service lines, IT Management and IT Optimization, and bundles its offerings into standardized packages so that clients get predictable value for money. IT Management covers ongoing support, monitoring and full ownership of a client's IT environment, including 24/7 support. IT Optimization covers strategic and consulting work, notably virtual CIO (vCIO) services that give smaller organizations access to senior IT leadership and IT investment planning without the cost of a full-time executive. Roxie I.T. also emphasizes compliance for regulated sectors, helping financial and healthcare clients work toward PCI and HIPAA compliance. Roxie I.T. is a small, owner-led business. Its owner and systems engineer is Kyle Benningfield, who named the company after his late mother; the name is described on the company's About page as both an honor and a reminder of the work ethic and values that guide the business. The team is deliberately lean, with Benningfield and systems engineer Jamie Southworth handling client environments. The company markets itself on relationships and a "human touch" as much as on technical competence, and it publishes client testimonials, such as one from Cathy Stafford, president of Ad-Venture Promotions. Geographically, Roxie I.T. focuses on the Lexington, Kentucky market and the surrounding region, serving local small businesses and entrepreneurs. Its messaging is aimed at passionate, community-oriented businesses that are building something special and do not want IT problems to distract them from their mission. The company maintains a website with service pages, pricing information, a blog and contact channels including a support email address and a toll-free phone number. It is a private, independent company and does not appear to be part of a larger corporate group.

History

Roxie I.T. is a managed IT services company based in Lexington, Kentucky. It was founded by Kyle Benningfield, who serves as owner and systems engineer. The company is named after Benningfield's late mother; on the company's About page he explains that she shaped his life and instilled the work ethic and values that guide how the business operates each day, and that naming the company after her is both an honor and a lasting reminder of her influence. From its base in Lexington, the company built its business around serving small businesses and entrepreneurs in the local market. Rather than operating as a traditional break-fix IT shop, Roxie I.T. adopted the managed service provider model, taking full ownership of clients' IT environments. Its service catalog grew to include IT management, IT optimization, cloud services, software management, central business systems, VoIP phone systems and technology strategy, along with compliance support for financial and healthcare clients working toward PCI and HIPAA requirements. A notable step in the company's development was the introduction of virtual CIO (vCIO) services under its IT Optimization line. This offering gives smaller organizations access to strategic IT leadership and IT investment planning without the cost of a full-time chief information officer. Roxie I.T. also standardized its services into two packages, which the company says allows it to deliver strong value for money and predictable outcomes. The company remains a small, owner-led practice. Its team consists of Benningfield and systems engineer Jamie Southworth, who together manage client environments. Roxie I.T. markets itself on reliability, security and cost-efficiency combined with a "human touch," and it highlights client relationships and testimonials, including one from Cathy Stafford, president of Ad-Venture Promotions, who described Roxie I.T. as "the engine that keeps us moving." The firm maintains a website with service pages, pricing, a blog and contact channels, and it continues to focus on the Lexington, Kentucky area.

  • Roxie I.T. is founded by Kyle Benningfield and named after his late mother.

  • The company adopts a managed service provider model, taking full ownership of clients' IT environments.

  • Roxie I.T. standardizes its services into two packages for predictable value.

  • Virtual CIO (vCIO) services are introduced under the IT Optimization line.

Products and positioning

A Lexington, Kentucky managed service provider that takes full ownership of small businesses' IT, offering quick, affordable, relationship-driven support with standardized packages and compliance expertise.

  • IT Management

    Ongoing managed IT support in which Roxie I.T. takes full ownership of a client's IT, including 24/7 support, monitoring and management of hardware, software and business systems.

  • IT Optimization

    Strategic and consulting services that align IT investments with business goals, including virtual CIO services.

  • Virtual CIO Services

    Strategic IT leadership and planning delivered without the cost of a full-time CIO, helping clients align IT with business objectives and streamline processes.

  • Compliance Support

    IT services for financial and healthcare clients working toward PCI and HIPAA compliance.

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