The verdict in three sentences
In Chicago, B2B software buyers (the CIO of a logistics group, the CFO of a Midwest manufacturer, the operations lead at an insurance broker) increasingly ask AI assistants like ChatGPT to draw up a first list of vendors and compare their integrations, compliance and pricing. A funded vendor whose product, security, pricing and integration pages are thin or contradictory lets the assistant fill the gaps, sometimes with false information about what the product does or which certifications it holds. Fixing that is priced on quote, roughly $4,000 to $12,000 for a diagnostic and $4,000 to $15,000 a month for a program (2026 ballpark), and it is measured by a dated record of answers to the same questions.
The questions Chicago buyers ask
Chicago concentrates logistics, freight, food, insurance and financial services: the questions reflect those industries and the systems already in place.
| Question asked | Typical buyer | Page that must exist on your site |
|---|---|---|
| "Freight audit software for a Midwest 3PL that integrates with our TMS" | Operations lead | A detailed integrations page, by system category |
| "Alternatives to [competitor] for accounts payable automation in manufacturing" | CFO | An honest, dated comparison page |
| "Which insurance software vendors have a SOC 2 Type II report?" | CISO | A trust center listing the reports actually held |
| "How much does production planning software cost for 200 users?" | CIO | A pricing page, or a clear explanation of the pricing model |
| "B2B software companies based in Chicago with Central time support" | Procurement lead | A company page: headquarters, teams, support hours |
| "Is [vendor] a good fit for a 500-employee company?" | Selection committee | Target customer segments and real case studies |
| "Implementation time for [vendor] at a food distributor" | Project manager | An implementation page with typical durations |
Why some vendors show up and others do not
AI assistants repeat what they can find and corroborate: your site, public documentation, software review platforms, trade press, funding announcements, integrator partner pages. The specific risk in B2B software is inaccuracy: an assistant that credits your product with an integration that does not exist or a certification you do not hold creates disappointment in the demo.
| Factor | Common state | What tends to help |
|---|---|---|
| Security and compliance page | "We take security seriously" | The reports actually held (SOC 2, ISO 27001), dates, subprocessors |
| Pricing page | "Contact us" and nothing else | The pricing model explained, ranges if your sales strategy allows |
| Integrations | A wall of logos | One page per integration, stating what syncs and in which direction |
| Case studies | Logos without context | Real cases approved by customers, with industry, size and type of outcome |
| Reviews | Few or old | Recent reviews on industry platforms, requested without misleading incentives |
| Consistency | Different customer counts across sources | One set of facts: founding year, headquarters, public funding, segments |
| Freshness | Release notes impossible to find | A dated, public changelog |
On compliance, there is no single federal privacy law in the United States. Illinois has specific statutes, including the Biometric Information Privacy Act for biometric data, and customers in other states, notably California with the CCPA as amended by the CPRA, may impose their own requirements. The CAN-SPAM Act governs email sequences, and a WCAG 2.1 or 2.2 AA target reduces the risk of ADA Title III claims. This is not legal advice.
What the work covers and what it costs
In broad terms: an audit of what assistants answer about the vendor and its category, correction of inaccurate facts at the source, factual pages (security, integrations, pricing, comparisons), presence on review platforms and in trade press, and regular measurement shared with the sales team. Budgets run higher than in other sectors because there is a lot of documentation to cover.
| Item | 2026 ballpark, Chicago market | Note |
|---|---|---|
| Initial diagnostic (40 to 80 questions) | $4,000 to $12,000 | Typical B2B agency quotes |
| Trust center and security page | $3,000 to $10,000 | Reviewed by the security team |
| Integration and comparison pages | $5,000 to $20,000 | Depends on number of integrations |
| Ongoing program | $4,000 to $15,000 per month | Content, reviews, mentions, tracking |
| Measurement only | $1,000 to $3,000 per month | Dated log, report to sales |
| Internal time (product, security, sales) | 4 to 8 hours per month | Essential for accuracy |
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These ranges come from typical agency quotes and public rate pages. Kolonell scopes this work on quote, after a diagnostic.
How do you measure it, and who should read the report?
A dated, monthly log of the same questions: the share of answers that mention the vendor, the accuracy of the facts (integrations, certifications, pricing), and which competitors are named instead. The report should go to sales as much as to marketing: a rep who knows what the assistant told the prospect prepares a better demo. Board members and investors also read it as a signal of awareness within the category. No provider can promise that an assistant will recommend your product.
Mini case study
Illustrative example. Ledgerline, a fictional 60-person vendor in Fulton Market, has raised a Series B and sells billing software for carriers. Across 50 questions logged in February, it appears in 6 answers, and 3 of them credit it with an integration it does not have. Budget under consideration: an $8,000 diagnostic, then $6,000 a month for six months, so $44,000. Written target for August: no nonexistent integration cited and a mention in 15 answers out of 50 (30%). With an average annual contract value of $40,000 (an illustrative assumption), the program is covered by just over one signed contract ($44,000 / $40,000 = 1.1). These figures frame the decision; they do not predict an outcome.
FAQ
Do B2B buyers really use AI assistants to shortlist software? Many use them to draw up a list of 3 to 5 vendors before contacting sales. Being absent from that list cuts the number of demos before the first form is ever filled in.
Do we have to publish prices to be cited? It is not required, but without information the assistant may quote an old or invented price. Explaining the pricing model (per user, per volume, setup fees) reduces that risk in most cases.
What if an assistant says we hold a certification we do not have? Publish a clear list of the reports actually held, with dates, and correct the third-party sources that get it wrong. Corrections often show up within a few weeks, sometimes 2 to 3 months.
How long before there is a measurable effect? Plan on 3 to 6 months of consistent publishing to be cited on category questions. Questions about your own name respond faster.
Can anyone guarantee ChatGPT will recommend our product? No. Answers vary by session and phrasing, and nobody controls them. What can be measured is the share of answers that mention you and their accuracy over time.
Find out how AI assistants describe your firm. We log what assistants like ChatGPT answer to your buyers' questions about your category and flag errors about your product. Request a diagnostic quote: reply within 48 hours.
Mohamed Bah
Fondateur, Kolonell
Passionate about digital and entrepreneurship in Africa, Mohamed has been helping Sénégalese businesses with their digital transformation since 2020. Founder of Kolonell, he believes every SME deserves a professional and accessible online présence.
