Sterling F. Cunningham

Founder, TaxAdvisor 360™ | Rettig-Spotlit | 24-Yr IRS, EA

Sterling F. Cunningham's profile photo
LocationLaurelMississippi, United States
Current roleCEOSterling Tax IQ · since May 2025
Government service14yrsInternal Revenue Service (IRS)

About

I turn IRS roadblocks into clear, defensible strategies.

Former IRS Insider → Revenue Agent (8 yrs) & Appeals Officer (16 yrs), now EA & CEO of Sterling Tax IQ.

What I Do

1. Representation – Defend owners and investors in audits, collections, and Tax Court prep.

2. Consulting for Pros – Coach CPAs/EAs/JDs through complex audits and appeals, adding “inside-the-Service” nuance to their briefs.

3. AI Tax Tools – Build IRS-trained AI Tax Assistants that cut research time and flag hazards before they cost you.

🔒 Sterling Tax IQ AI Tax Assistants run on FedRAMP‑High Amazon Bedrock, encrypted Amazon S3, and SOC 2‑certified Pinecone. No prompts are ever used to train models, and our PII Shield auto‑redacts SSNs/EINs before processing. Full stack inherits SOC 2 and NIST 800‑53 controls—see aws.amazon.com/artifact and pinecone.io/security for details.

Highlights

• Handled 1,000s IRS disputed cases + Appeals conferences—resolving disputes up to docketed litigation.

• Drafted national Appeals policy updates & trained frontline agents & Appeals Officers

• Former Fortune 500 business-systems analyst (GE Power, Home Depot)—I translate tax law into repeatable processes.

Let’s connect if you need battle-tested IRS insight or AI that thinks like the Service.

SterlingTaxIQ.com 
“Beyond Expertise”

Roles

May 2025–Present
Current role

CEO

Sterling Tax IQ

Taylorsville, Mississippi

Appellate Litigation

As an Enrolled Agent and CEO of Sterling Tax IQ I am directly responsible for managing the three core business areas:
1) IRS Audit & Appeals defense & representation
2) IRS Audit & Appeals defense consulting to licensed tax professionals and
3) IRS custom GPT development.

I bring more than 8 years as a former IRS Revenue Agent; 16 years as a former IRS Appeals Officer and 5 years as a former Sr. Business & Systems Analyst experience to these roles.

Aug 2020–May 2025
Former role

Appeals Officer GS-13

Internal Revenue Service (IRS), Appeals

Mississippi

Appellate Litigation

Key Accomplishments:

- Resolution of Complex Cases: Successfully resolved numerous high-stakes, docketed tax cases in collaboration with IRS Chief Counsel.

- Policy Contributions: Contributed to nationwide IRS Appeals policies, ensuring compliance and consistency.

- Training and Mentorship: Mentored junior Appeals Officers and served as an on-the-job instructor, fostering a culture of knowledge-sharing and professional growth.

Aug 2005–Aug 2010
Former role

Internal Revenue Agent GS-13

Internal Revenue Service (IRS), SB/SE

Georgia

Auditing

Responsibilities included field auditing of individual, corporate, and partnership returns as well as financial books and records relative to the technical requirements of GAAP and the Internal Revenue Code. Extensive tax law research and position case write-up was involved. Research included analysis and interpretation of law code, regulations, private letter rulings, tax court cases, district court case, and Supreme Court cases.

I consistently displayed a working knowledge of tax laws and research tools to independently conduct relevant research. I also consistently conducted appropriate research using the Code, Regulations as well as court cases to support the conclusions reached.

I consistently demonstrated a working knowledge of tax and financial accounting principles and utilized such to understand, reconcile and analyze books and records and financial statements.

I consistently identified and resolved issues and areas where compliance was questionable. I also recognized and considered indicators of fraud when present.

I consistently conducted tasks in a complete, understandable, accurate and logical manner.

I consistently cited the appropriate authority and followed established rulings and precedents when making determinations.

I consistently obtained and evaluated taxpayer's positions, weighing the merits of those positions during case development. I consistently explained taxpayer's options for agreement and payment.

I consistently showed the ability to work independently as well.

Promoted to GS-512-12/13 June of 2008.

Training and Mentorship: Mentored junior Revenue Agents and served as an on-the-job instructor, fostering a culture of knowledge-sharing and professional growth.

Jun 1995–May 2005
Former role

Sr. Business & Systems Analyst

Sterling Technical Services

Atlanta, Georgia

Business Systems Analyst

As a self-employed accounting & systems analysis consultant:

Clients included: Home Depot, GE Energy Services, KPMG, American Cancer Society

IN INFORMATION TECHNOLOGY:
Acted as a Senior Business & Systems Analyst for various clients. Primary goal was to assist in development of business systems process improvements and software development to manage administrative and operational programs as well as major customer processes. Focus was on enhancing business processes to improve organizational effectiveness.

Planned, coordinated, conducted, managed and evaluated business process analytical studies for major software development projects. Conducted design meetings, needs assessments, business process analysis, and developed requirements definitions through Joint Application Development meetings. Utilized Object Oriented Analysis and Object-Oriented Design modeling techniques to develop Use Cases, Interaction Diagrams, and Activity Diagrams as necessary for clarification. Designed, developed and documented web user interfaces and functional specifications. Developed test scenarios and documented test plans based on detailed business requirements.

Documented functional specifications based on user interfaces for developer build process.

Conducted high level design meetings that included senior management. Meeting participants included senior finance and senior IT members as well as IT Track and Team Leads. Investigated application issues and drove resolutions by documenting and preparing requirements so developers would have a better understanding of the issues involved which resulted in the correction of major problems.

Jan 1991–May 1995
Former role

Internal Revenue Agent GS-11

Internal Revenue Service (IRS), SB/SE

Georgia

Auditing

Responsibilities included field auditing of individual, corporate, and partnership returns as well as financial books and records relative to the technical requirements of GAAP and the Internal Revenue Code. Extensive tax law research and position case write-up was involved. Research included analysis and interpretation of law code, regulations, private letter rulings, tax court cases, district court case, and Supreme Court cases.

I consistently displayed a working knowledge of tax laws and research tools to independently conduct relevant research. I also consistently conducted appropriate research using the Code, Regulations as well as court cases to support the conclusions reached.

I consistently demonstrated a working knowledge of tax and financial accounting principles and utilized such to understand, reconcile and analyze books and records and financial statements.

I consistently identified and resolved issues and areas where compliance was questionable. I also recognized and considered indicators of fraud when present.

I consistently conducted tasks in a complete, understandable, accurate and logical manner.

I consistently cited the appropriate authority and followed established rulings and precedents when making determinations.

I consistently obtained and evaluated taxpayer's positions, weighing the merits of those positions during case development. I consistently explained taxpayer's options for agreement and payment.

I consistently showed the ability to work independently as well.