Sterling F. Cunningham is a nationally recognized IRS procedure expert and technology
innovator with over 24 years of combined IRS service. His career spans a rare spectrum of
roles—including IRS Agent, Appeals Officer, Instructor, Policy Analyst, and Business Systems Analyst – giving him a uniquely comprehensive perspective on federal tax administration and compliance.

Sterling’s distinctive blend of frontline IRS operational experience and advanced technology expertise enables him to develop AI-driven solutions that address real-world challenges tax professionals face in dealing with the IRS. His leadership with the IRS included managing nationwide Appeals programs, spearheading analytical projects, and providing strategic vision for systematic improvements. 

In the private sector, Sterling’s work as a Senior Business Analyst for Fortune 500 clients further honed his ability to translate complex regulatory and business requirements into practical, technology-enabled solutions. This duel expertise ensures that his AI applications are not only grounded in deep procedural knowledge but are also robust, user-centric, and aligned with professional standards.