# Rachel Toomey, Director of Technology at Midwest Regional Mutual — read of ChatGPT Capability Assessor, June 13 2026

> 14 years in insurance tech, currently managing a team of 6 that nobody asked to become AI experts but here we are.

## How I got here

LinkedIn ad. The targeting was "AI readiness" and it hit my feed during my 7:20 train from Naperville. I screenshot it to look at later and then actually did, which is more than I do for 90% of these ads. The phrase "hard limits" got me. Every vendor I've talked to this year says AI will do everything. Someone promising to tell me what it *can't* do felt different.

## What I clicked first

The subhead stopped me: "By the time you find out what doesn't work, you've already staked the roadmap on it." That's the first thing I've read in six months that describes my actual problem, not a solution someone wants to sell me. We just wrapped a four-month pilot on claims summarization that went nowhere. Nobody told us ahead of time it would hallucinate policy numbers.

## Where I paused

Scrolled past the features, which looked fine, and then hit this block: "The Wishdeal Factory scores every idea against 10 Adoptability axes." And then: "52/100 Adoptability. 1 in 7 Meaningful-success odds."

I read that three times. I genuinely did not understand what I was looking at. Am I reading a product page or a pitch deck for a startup that doesn't exist yet? Why is the product homepage telling me the product has a 1-in-7 shot at working?

## What I distrusted

Everything after that Wishdeal section. Specifically: "Honest disclosure: we don't have live customers on this idea yet. We shipped the strategy package; you ship the customer conversations."

So this is not software I can buy. This is an idea someone built a strategy package around and is now selling to people who might want to go build the actual thing. The $49/month plan and the "Start Free Assessment" button above it are hypothetical. The product doesn't exist.

I went back and re-read the whole page with that context and it reframes everything. "Pre-Built Scenarios" for legal, finance, customer service: probably described in a document somewhere. "Exportable Report": a PDF template, maybe. "Assessment Wizard": a Google Form or Notion workflow.

The hero copy is good. The problem framing is good. And then the page undercuts itself completely by telling me I'm looking at a Fermi estimate and a pitch, not a product.

## What would convince me

I came here looking for something I could log into next week and run my team through. If this was real software with even 10 paying teams using it, I'd want to see one of their actual exported reports -- not a sample, a real one with the company name redacted -- showing me a capability map for a use case similar to insurance claims. That would get my attention. The problem framing is genuinely good. The execution proof is zero.

## What I'd ask in an email reply

1. Is there working software I can access today, or is the "Start Free Assessment" button leading somewhere that doesn't exist yet?
2. If this is a concept you're looking for a builder to take on, why is the landing page written as if the product is live?
3. The $49/month plan says "unlimited assessments and custom scenarios" -- what does the actual workflow look like right now? Walk me through one assessment start to finish.

## Verdict: dismissive

The problem statement is the best I've seen this year for AI evaluation tooling. But I can't tell if this is a product or a business plan for sale, and the page is actively unclear about which one it is. If the software exists, bury the Wishdeal scoring section -- it makes the whole thing feel like a concept deck. If it doesn't exist, don't run ads driving buyers to a page with a "Start Free Assessment" button.

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*Memo by skeptic persona, generated 2026-06-13. Studio breaks own self-grading loop.*