Sterling F. Cunningham Founder & CEO, Sterling Tax IQ — “Beyond Expertise”. As a former IRS Agent (8 yrs), former IRS Appeals Officer (16 yrs) & current Enrolled Agent, I built Sterling Tax IQ’s custom GPT suite: 13 AI-powered assistants that think the way the IRS actually operates—guiding practitioners from first notice through Appeals, collection defenses, penalty relief, crypto issues, and even bankruptcy tax discharge. TRY OUR APPS FOR FREE WITH 30 CHATS. JUST CLICK ON AN APP BELOW!
The Appeals Advisor 360™ is designed to assist users in preparing professional and effective protest letters for IRS appeals. It utilizes authoritative sources and ensures accurate application of tax laws.
A compliance-focused assistant providing step-by-step guidance, conversational advice, and detailed documentation for IRS Collection defense strategies, tailored to licensed tax professionals and non-experts alike.
A specialized IRS Penalty Abatement GPT, explicitly designed to educate and assist individuals, small business owners and licensed tax professionals in effectively navigating IRS penalty abatement processes.
This GPT is designed to simulate an experienced IRS agent, tax advisor, and audit defense strategist. It helps users evaluate whether they qualify as a Real Estate Professional under IRC §469(c)(7), understand passive activity loss rules, and avoid common IRS red flags.
A custom GPT built to educate, simulate, and guide users on the IRS Trust Fund Recovery Penalty (TFRP) under IRC §6672. This assistant simulates IRS education logic for: Audit and Form 4180 prep - Appeals readiness and CDP - Legal risk awareness (responsibility & willfulness) - Litigation hazard recognition - Fictional case walk-throughs based on real IRS training.
Basic
$175.99
/mo
What's included?
✔ 600 credits per month
✔ Appeals Letter protest Builder, Collection Defense, Penalty Abatement, Tax Advisor 360 & TaxPrompt Advisor + Monthly 30-min strategy call
Appeals & Pre-litigation
$275.99
/mo
What's included?
✔ 1000 credits per month
✔ Appeals Letter Protest Builder, (Audit, Appeals & Research), Appeals & Litigation Guide & TaxPrompt Advisor + Monthly 30-min strategy call
Enterprise
$495.99
/mo
What's included?
✔ 3000 credits per month
✔ Appeals Letter Protest Builder, Collection Defense, Penalty Abatement, Real Estate Pro, Trust Fund Recovery Defense, Tax Advisor 360, (Audit, Appeals & Research), Appeals & Litigation, Claims Guide & TaxPrompt Advisor + Monthly 30-min strategy call
👋 Sterling F. Cunningham
👋 Hi, I’m Sterling F. Cunningham founder & CEO, Sterling Tax IQ — “Beyond Expertise”. After 24 years inside the Service—as an IRS Agent, Appeals Officer, Policy Analyst, Instructor, and Business Systems Analyst—I saw first-hand how even seasoned tax pros struggle with shifting procedures, looming penalties, and opaque IRS logic. So I built Sterling Tax IQ’s custom GPT suite: 13 AI-powered assistants that think the way the Service actually operates—guiding practitioners from first notice through Appeals, collection defenses, penalty relief, crypto issues, and even bankruptcy tax discharge. My aim is simple: turn insider know-how into everyday leverage for EAs, CPAs, and attorneys who don’t have time to decode the IRM on every case. Each module validates citations in real time, flags procedural deadlines, and stays Circular 230-conscious—so you can focus on strategy, not statute-hunting. Today I’m focused on expanding that edge—making IRS-savvy AI smarter, more intuitive, and accessible to every small-firm practice that wants to punch above its weight. Ready to see how an AI that thinks like the IRS can safeguard your clients? Book a no-cost 15-minute demo and let’s redefine tax controversy work—together. 🚀
