Jason Cox

About Jason Cox

As the visionary leader of CSS, Inc. a Veteran Owned Small Business, I am dedicated to steering our organization towards a future where custom Microsoft 365 (M365) solutions empower businesses across all industries. Our mission transcends boundaries, as we strive to architect and deliver tailored M365 ecosystems that seamlessly integrate with each client\'s unique needs, revolutionizing the way they operate in an ever-evolving digital landscape.At CSS, Inc, we are propelled by an unwavering commitment to innovate and craft forward-thinking IT strategies that anticipate the demands of tomorrow. With an exceptional ability to transform complex technical challenges into bespoke, actionable solutions, we harness the full potential of M365 to drive enterprise-wide transformation. My extensive experience as an IT director has honed a rare blend of expertise—spanning strategic operations, process optimization, and masterful project management—which I now channel into delivering unparalleled M365 solutions that elevate productivity, collaboration, and efficiency for organizations in every sector.From manufacturing to healthcare, finance to education, our vision at CSS, Inc. is to redefine how industries leverage technology by providing custom M365 implementations that align with their specific goals. Whether it’s designing intuitive SharePoint environments, streamlining workflows with Power Automate, or enhancing communication through Teams, we tailor every solution to unlock new possibilities for our clients. Our rich legacy of advancing IT infrastructure empowers us to bridge the gap between ambition and achievement, ensuring that businesses of all kinds thrive in a digitally empowered era.Together, we at CSS, Inc. are forging a path toward a future where every industry benefits from the transformative power of custom M365 solutions, setting a new benchmark for excellence, adaptability, and success in the modern workplace.

Experience

1. CEO of Css, Inc

   Css Llc

   Aug 2021 — Present · Pittsburgh, PA, US

   President & Founder | AI-Driven Digital Transformation LeaderVeteran business owner leading a Small Business Administration–registered SDVOSB/VOSB enterprise focused on advanced AI integration and enterprise modernization. Spearheads strategic initiatives using Microsoft Copilot, Copilot Studio, and Microsoft 365 technologies to drive operational efficiency, automation, and intelligent decision-making across departments. Oversees Managed Services offerings that include cybersecurity, cloud infrastructure, and digital workplace solutions tailored for scalable growth.Expert in:Microsoft Copilot Enterprise deploymentCopilot Studio agent developmentSharePoint architecture & automationAI strategy consulting for sales, finance, operations, and executive teams#MicrosoftCopilot #CopilotStudio #AITransformation #SharePointOnline #MSP #SDVOSB #VOSB #DigitalWorkplace #VeteranOwned

Education

• John Carroll University

  B.A., History, International Relations

  2000 — 2004

• Robert Morris University

  MS degree, IT Project Management

  2018 — 2020