Are You Ready to Turn On Your Vendors' AI Features?
Every SaaS vendor is shipping AI features. Score whether you should turn them on, hold off, or evaluate one-by-one.
- A scored profile across 6 dimensions — see exactly where you're strong and where the gaps are.
- Your biggest opportunities, mapped to specific next moves.
- A personalized video walkthrough from Shawn (optional) — a real read on your results.
Every SaaS vendor in your stack is shipping AI features faster than your procurement, legal, and security teams can evaluate them. Copilot is in Microsoft 365. Einstein is across Salesforce. Fin is in Intercom. Gemini is in Google Workspace. Each one ships with a different data boundary, a different training posture, a different audit capability, and a different opt-out granularity — and the decision to turn them on, hold off, or evaluate one-by-one is landing on executive desks every week with very little structure behind it.
This free scorecard scores your readiness to enable vendor AI features across six dimensions in about five minutes. It's built from 27 years of technology leadership across Fortune 500 and growth-stage companies — the same lens a fractional Chief AI Officer would bring to your first conversation about which features to enable, which to hold off on, and which deserve case-by-case evaluation.
What the SaaS AI feature readiness scorecard measures
Readiness is a profile, not a single number. The scorecard scores six dimensions independently so you can see exactly where you're ready and where the gaps sit: Data Posture (whether your data leaves your perimeter when these features fire), Contractual Posture (whether existing agreements cover what the vendor is now doing), Audit & Compliance (whether you can produce the audit trail a regulator will ask for), Opt-out & Granularity (whether you can turn AI on for one team but not another), Change Management (whether the org actually uses new features or just enables them), and Vendor Concentration Risk (whether enabling AI across multiple vendors creates lock-in to the same underlying model providers). The final question maps the specific vendor AI features you're weighing right now.
Why this decision can't wait for next year's planning cycle
The default path most organizations are on is to leave AI features off until 'we figure it out' — which becomes a six-month delay during which competitors enable, adopt, and learn faster. The other failure mode is the opposite: flip the switch on everything because the vendor said it was safe, then discover at audit time that prompts and outputs aren't logged, that your DPA doesn't address training, and that a single workflow created concentration risk you didn't price. The teams that get this right are running a tiered approach: enable low-risk features inside vendors with the strongest contracts and audit posture, hold off on the rest, and revisit at every renewal. A readiness profile turns a vague backlog into a sequenced turn-on list and a defensible hold-off list.
What you get at the end
You'll see an overall SaaS AI feature readiness score, a band that describes where you stand (from Hold Off through Enable Decisively), a per-dimension breakdown, and a map of the specific vendor features you flagged for evaluation. From there you can request a personalized video walkthrough — a short, recorded read on your results and what a fractional Chief AI Officer engagement would do for your turn-on decisions. No generic sales deck.
Frequently asked questions
What is a SaaS AI feature readiness assessment?
It's a structured evaluation of whether your organization has the data posture, contracts, audit infrastructure, granular controls, change-management capacity, and concentration-risk awareness to defensibly turn on the AI features your existing SaaS vendors are shipping. Rather than measuring AI knowledge, it measures the controls — training opt-outs, audit logs, per-team granularity, adoption capacity — that determine whether enabling a vendor's AI feature creates value or creates exposure.
How long does the assessment take?
About five minutes. It's 17 scored questions across six dimensions plus a final vendor-mapping question covering productivity, CRM, support, developer tools, HR and finance, and marketing. Your progress auto-saves, so you can leave and resume without losing answers.
Is the assessment free?
Yes. The assessment and your scored results are completely free. You can optionally request a personalized video walkthrough of your results, which is also free.
Who is this assessment for?
It's built for CIOs, CISOs, general counsel, heads of procurement, and operating executives who are weighing whether to turn on the AI features their SaaS vendors are now shipping — and want a clear-eyed read on which to enable, which to hold off on, and which deserve case-by-case evaluation.
Should I just turn on all the AI features and see what happens?
No. The default flip-the-switch approach inherits risk you can't yet measure: training data exposure, audit blind spots, opt-out gaps, and concentration to a single model provider across half your stack. A tiered approach — turn on low-risk features inside vendors with strong contracts and audit posture, hold off on the rest until specific gaps close — produces better outcomes than either blanket enablement or blanket avoidance.