AI Readiness Assessment for B2B SaaS

What's your role?

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Domain 1 of 3: Nature of technology

What people think the AI does

Do the groups in your organization share a common understanding of what the AI initiative actually is?

1. If you asked your IT lead, your CEO, and three GTM team members to describe the AI initiative in two sentences, how similar would their answers be?

Very similar. Everyone would describe the same thing. Mostly similar. Minor differences in emphasis. Noticeably different. Each group would focus on different capabilities. Very different. Some groups would struggle to describe it at all.

2. How do GTM team members interpret this AI initiative relative to tools they already use?

They understand it as a new capability with distinct use cases for their GTM workflows. They see it as an upgrade to an existing tool in their stack. They're mapping it onto tools that aren't really comparable. Most team members haven't formed an opinion or are confused about what it does.

3. Has your organization communicated what the AI initiative is and isn't designed to do?

Yes. Specific GTM use cases and boundaries were communicated to every team. Partially. A general announcement went out but without GTM-specific detail. Barely. Most people heard about it through Slack or hallway conversation. No. People are finding out about it as it lands on their desk.

4. Do the people championing the initiative describe its value in terms of specific GTM workflows, or in abstract terms?

Specific workflows and concrete GTM outcomes. A mix of both. Mostly abstract. The vision is clear but the GTM application is vague. Almost entirely abstract. It's being sold on potential, not specifics.

Domain 2 of 3: Technology strategy

Why the organization bought it

Do groups agree on the motivation for adopting AI and how success will be measured?

5. Is there a shared understanding of why the organization is pursuing this AI initiative?

Yes. The rationale is clear, specific to GTM goals, and widely understood. Leadership has a clear vision, but not every GTM team knows it. Different teams have different assumptions about the "why." People are guessing. Cost reduction, innovation, competitive pressure, nobody's sure.

6. How is success defined at 90 days?

Clear GTM business metrics everyone knows and agrees on. Defined but not widely communicated. Leadership knows, the GTM team doesn't. Vague. Defined in deployment terms (users onboarded, tools configured) not business impact. Not defined. There are no shared success criteria.

7. When does each group expect to see results?

Timelines are aligned and realistic across groups. Mostly aligned, with some minor gaps. Significant gaps. Leadership expects fast ROI while IT plans a longer rollout. Nobody has discussed timelines across groups.

8. Who absorbs the failure if this doesn't work out?

Accountability is clear and has been discussed openly. Implicitly understood but not formally addressed. Unclear. Different groups would point to different people. Nobody has discussed this. If it fails, the technology will be blamed.

Domain 3 of 3: Technology in use

How it changes day-to-day work

Do the people whose daily GTM workflows change understand what's expected of them?

9. What training and support is planned for the GTM team members who will use this daily?

Role-specific training tied to actual GTM workflows, with ongoing support. General training is planned, but it's not tailored to specific GTM roles. Minimal. A demo or documentation, then people are expected to figure it out. None. The assumption is the tool is intuitive enough.

10. Do the people who will use this daily understand how their specific GTM workflow changes?

Yes. They've been involved in planning and know what's expected of them. Somewhat. They know it's coming but not exactly how their workflow changes. Barely. They've heard about it but haven't seen how it applies to their work. No. They'll find out when it shows up.

11. Have policies around data quality, customer data, and appropriate use been updated for AI-generated output?

Yes. Clear policies for AI-generated GTM content, customer communications, and data handling. In progress. The issues are recognized but policies aren't finalized. Partially. Some policies exist but haven't been updated for AI output. No. The assumption is existing review processes cover it.

12. Who bears the burden of change, and do they know it?

The people whose GTM work changes most have been identified, consulted, and supported. They've been identified but not deeply involved in planning. It's unclear who will be most affected. The burden is falling on the GTM team and nobody has acknowledged it.

AI readiness assessment

What's your role?

What people think the AI does

Why the organization bought it

How it changes day-to-day work

Where frames are likely to diverge

Do groups agree on what the AI does?

Do groups agree on why and how to measure success?

Do groups agree on how daily work changes?

What to do next