Before You Sign an Enterprise AI Contract: 7 Questions Every Cayman Corporate Board Must Ask

By Leonard Lewis, Co-Founder of Caydev

Corporate leaders, partner committees, and enterprise boards are approaching enterprise AI the way they approached software in 2015: pick a platform, sign a contract, plug it in. That worked for software solutions where there weren’t many alternatives, and most niches had a single dominant solution. Unfortunately, this doesn’t apply to production-level enterprise AI. The “platform” decision is really multiple decisions stitched together, and many AI contracts and solutions I see in the corporate market cover one or two of them while leaving the others on the buyer’s desk.

The local context is not theoretical. Cayman’s regulators and statutory bodies have made digital transformation, regulatory technology, and AI-enabled analytics priorities across recent strategic plans and procurements. Controls aligned with NIST (the US National Institute of Standards and Technology) and GDPR (the EU General Data Protection Regulation) increasingly appear as baseline expectations in public-sector (and increasingly private-sector) RFPs (request for proposal). The Cayman Islands Data Protection Act underpins all of it.

Below are seven questions every corporate board should ask before signing. They belong on the desks of your vendor, CIO, compliance lead, and procurement team.

1. If pricing changes or the AI provider (e.g. LLM, Large Language Model vendor) falls behind, how hard is it to move? Lock-in is the line item nobody prices. A vendor that hard-codes today’s model sells next year’s rebuild.

2. Who owns the instructions, business logic, knowledge base, and anything tuned on our data? Will the vendor train their public models on your prompts or client data? For a regulated firm, the wrong answer ends both conversation and project.

3. How does the system handle data security and incidents (eg. storing a passport number, handling data breaches and leaks, or mitigating AI prompt injection from an email)? Where the Data Protection Act and GDPR-style controls live. Personal-data redaction, prompt-injection detection, secrets handling. The one question I would refuse to sign without.

4. What stops usage, errors, or automated actions from running beyond budget? Documented cases overseas show AI agents generating five-figure cloud bills overnight. Without a hard stop, that liability is yours.

5. Which systems can the AI touch, and with whose credentials? The AI cannot act on your systems with unchecked admin credentials. Role-based permissions and a full audit trail are a must.

6. When a client claims the AI told them something wrong, can you show me the conversation? Full logging, retention matching regulator expectations, searchable and exportable. The absence of an audit trail is the absence of compliance.

7. When the underlying AI model changes, what testing happens before it touches our clients? A regression-test suite is key. Without one, your clients become the testers.

 These seven decisions don’t replace normal procurement processes. Data residency, exit clauses, SLAs, audit rights, SOC 2 and ISO 27001 certifications, subprocessors, and business-continuity plans still apply, and matter more, not less, in an AI context.

Corporate and enterprise clients carry a harder responsibility: introducing modern AI into industries where the risks and lack of trust often outweigh the upside, especially in risk-averse fields like finance, legal, and government.

Businesses should still invest in understanding these technologies and resource them, or face falling behind competitors and losing the trust and loyalty of their clients and employees.

If a vendor cannot tell you, in plain language, how they handle all seven decisions, they are not selling you production AI. They are selling you a demo with an invoice attached.

If your firm is approaching an AI procurement and isn’t sure which questions to put in front of the vendor, that is the first conversation we have at an AI Readiness Audit. Visit https://www.caydev.com/consult  to book a chat with us.