The Playbook
The Playbook: AEO, AI, and compliance for insurance agencies.
Build guides, explainers, analysis, and original research for insurance agencies. Every post is anchored to named data and written to be cited by AI engines. The badge on each card tells you which kind it is, and every build guide is collected on one page.
Florida's Medicare Advantage Plans Can Now Close Mid-AEP for 2027
Humana's non-renewal letters for up to 600,000 Medicare Advantage members are landing now, and new CMS rules let the replacement plans close to new enrollees with no public warning. Florida carries the second largest Medicare Advantage population in the country. What the rule actually says, sourced live from CMS, Humana's own earnings call, and SEC filings.
Sep 30, 2026
AnalysisCan Your Website's AI Chatbot Get Your Agency Sued?
A BC tribunal already ruled a chatbot is "just part of" a company's website and ordered Air Canada to pay for what it told a customer. Twenty five states have adopted the NAIC's AI bulletin, and the ISO added a generative AI exclusion to commercial forms in January 2026. What a bolt-on chat widget can cost an agency, and how to build one that can't invent an answer.
Sep 29, 2026
GuideBook AI Appointments on the Assigned Agent's Calendar
A no-code, step by step build: make your AI caller or chat agent book every appointment on the calendar of the agent who owns the lead. Seven click-by-click GoHighLevel steps with a check after each one, or paste our exact prompt into Codex and let it do the setup. From Victoria Cabrera's walkthrough on our Friday open mic.
Sep 28, 2026
AnalysisIs Your Insurance Agency's WordPress Site a Security Risk?
Patchstack counted 11,334 new WordPress vulnerabilities in 2025, 91% of them in plugins. On September 28, 2026, 55% of installs of one 5 million install backup plugin were still on a version older than its fix. What that means for an agency site, the 72 hour state notice clock, and how to shut it down.
Sep 28, 2026
ExplainerDoes Your CRM Integration Need to See Raw Client PHI?
Cyberhaven found 39.7% of AI interactions now carry sensitive data, and most CRM-to-AI integrations send the whole client record by default. What actually crosses the wire when you connect an AI tool, and how to check your own stack this week.
Sep 27, 2026
ExplainerWhy Your Agency's Spanish Page Never Gets Cited by AI
Latino consumers are now 29.4% of HealthCare.gov plan selections, up from 20.4% in 2020, and Texas and Florida alone hold more than 18 million Hispanic residents. A 3.25 billion citation study shows AI treats a Spanish query as its own source pool, not a translation. Sourced live from ASPE, Census, Profound, and Google.
Sep 26, 2026
ExplainerWhy ChatGPT Never Names Your Agency for Annuities
Annuity sales hit a record $464.1 billion in 2025, and 79% of American adults still can't define the product. The vertical almost no agency site answers, sourced live from LIMRA, Policygenius, and NAIC.
Sep 25, 2026
AnalysisYour Medicare Website's TPMO Disclaimer Changed for 2027
CMS removed the SHIP reference from the required Medicare TPMO disclaimer and changed when it must be given, effective for CY2027 materials on October 1, 2026. What every agency website, funnel, and script needs to fix before AEP, sourced live from CMS and the federal regulation.
Sep 24, 2026
AnalysisThe Medicare Drug Cost Cap Just Jumped to $2,400 for 2027
CMS finalized the 2027 Part D deductible at $700 and the out-of-pocket cap at $2,400, up from $615 and $2,100. What a static agency cost calculator misses, and what a live one built from one source of truth catches before AEP opens. Sourced live from Medicare.gov, CMS, and KFF.
Sep 23, 2026
ExplainerYour Google Business Profile Is Feeding AI the Wrong Info
Google's own documentation names Business Profile and Merchant Center as inputs to its AI answers, and says the data is compiled from four sources, not just what you typed. Whitespark scores primary category the No. 1 local ranking factor. Sourced live from Google, Whitespark, BrightLocal, and Ahrefs.
Sep 22, 2026
AnalysisRanking Isn't What Gets Insurance Agencies Cited by AI
Ahrefs found only 38% of AI Overview citations rank in Google's top 10, down from 76% a year ago. Conductor found the same pattern in insurance search specifically, and the biggest named brand holds under 3% of citations. Sourced live from Ahrefs, Conductor, and Google Search Central.
Sep 21, 2026
GuideWhat an AI-Built Insurance Website Actually Costs to Run
An agent paid $500 in AI fees for a 15 page site. The same build cost about $3 on a flat plan. Where the markup hides in per call billing, the four rules that keep it off your card, and how the inexpensive build is actually assembled.
Sep 21, 2026
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