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ClelandCo

Standing advisory — AI Strategic Advisor

Scoping conversations

A senior second opinion on what to build, what to buy, and what to stop.

Your team can build it. The missing question: should you?

A standing advisory seat for teams already building with AI: scoped roadmap scoring, documented build-versus-buy criteria, vendor review, and review of actual in-scope artifacts. Your leadership still decides. I pressure-test the evidence and write the record.

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Briefing

This engagement is designed for a team that retains implementation authority but lacks recurring senior review. The review asks three questions: does the evidence support the decision, do vendor claims hold under expected conditions, and does the roadmap name testable outcomes rather than features alone?

Those questions are easier to answer before a contract is signed or a system carries material work. The advisory seat puts the criteria and decision record in place while the options are still open.

The proposed cadence is a weekly working session reviewing the client team’s actual in-scope code changes, evaluations, deployment evidence, and vendor materials. A named between-session channel has written response boundaries. The monthly record captures client decisions, supporting evidence, open questions, and conditions that would reopen them.

What you keep is a decision record and evaluation criteria your team can run after I leave.

Three ways forward

Three options. One recommendation.

01

Hire a full-time AI lead.

The right answer when the mandate is genuinely full-time and already clear. If the role is still being defined, the assessment should establish the outcomes and authority before a permanent search begins.

02

Bring in a consultancy.

A project consultancy is appropriate when the deliverable can stand alone. It is a weaker fit when the need is recurring judgment as the roadmap meets delivery constraints.

03

Add a senior second opinion.

A standing seat with the people building, sized to senior review rather than delegated operating authority, ending in criteria your team keeps.

How the engagement starts

Two scopes. One decision at a time.

The normal starting point is the assessment. It is self-contained and yours to act on regardless of what happens next — including when it recommends doing nothing.

AI Adoption Assessment

Bounded first step

Fixed diagnostic

One time, 1 to 2 weeks

A written read on where AI is worth spending, what has to be true before anything ships, and what to do first. The same assessment starts both leadership alternatives; it ends with a direct recommendation about which, if either, is justified — including when the answer is neither.

Scope is set by

The stakeholder groups, active use cases, systems, vendor decisions, and risk context to review.

AI Strategic Advisor

Optional standing engagement

Standing engagement

Three-month initial term, reviewed each quarter

An advisory seat for teams already building with AI: a scored use-case roadmap, build-versus-buy recommendations, vendor evaluation, review of work in flight, and criteria the team can run without me.

Scope is set by

The use cases, systems, vendor decisions, stakeholder groups, and risk requirements under review.

Discuss an AI Adoption Assessment (opens in a new tab)

AI Adoption Assessment

Commitment

One time, 1 to 2 weeks

Scope is set by

The stakeholder groups, active use cases, systems, vendor decisions, and risk context to review.

A written read on where AI is worth spending, and what to do first.

Format

  • Separate interviews with the people building and the people funding so their descriptions of the roadmap, evidence, and authority can be compared
  • A use-case inventory scored against client-approved value and feasibility criteria, with explicit continue, defer, stop, and unknown recommendations
  • A data-handling, evaluation, deployment, monitoring, and governance evidence-gap review mapped to stated questions, without a compliance or audit-readiness opinion
  • Build-versus-buy guidance per use case with criteria and assumptions recorded, plus technical and commercial review of vendor materials already in flight; legal terms remain with counsel
  • A roadmap prioritized under the agreed criteria and a recommendation on whether ongoing work is justified, including when the answer is no or not yet
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The AI Adoption Assessment, a fixed diagnostic that stands on its own.

This is right for you if…

You have a team building AI and a roadmap that needs independent technical pressure-testing before a vendor, hiring, or engineering commitment. It is the same assessment the fractional mandate starts with; what differs is the recommendation it ends in.

AI Strategic Advisor

Commitment

Three-month initial term, reviewed each quarter

Scope is set by

The use cases, systems, vendor decisions, stakeholder groups, and risk requirements under review.

A standing weekly seat with the people doing the build.

Format

  • A use-case inventory scored by value and feasibility, including an explicit list of what not to do and why.
  • A written build-versus-buy recommendation per use case, with criteria that can be re-examined when conditions change.
  • Vendor evaluation: a shortlist, the questions to ask, and the failure modes to test before signing.
  • A review of work already in flight, covering data handling, evaluation, deployment path, cost, and monitoring.
  • Evaluation and governance criteria written so your team can run them after the engagement ends.
  • A rehearsal plan from the AI Contingency Framework for your team to execute, covering the failure modes relevant to the system.
  • Working sessions with the engineers and leads doing the build, anchored to real artifacts rather than a generic workshop.
Discuss an AI Adoption Assessment (opens in a new tab)

A standing weekly working session with the people doing the build, defined async availability between sessions, and a written monthly decision record.

This is right for you if…

Your team owns implementation, but decision rationale is not consistently recorded, so choices keep getting reopened. You want senior judgment in the room every week, not a document once a quarter.

Fit

Worth knowing before you call.

Signals this engagement may fit

Executives and founders with an in-house team already building AI who need senior judgment without handing over the mandate.

  • Your engineers are shipping AI features and the evaluation criteria are still unsettled.
  • You are approaching a vendor decision and need the production risks examined before signing.
  • The roadmap is a list of features rather than outcomes with stop conditions.
  • The team can execute, but the same build-versus-buy or governance decisions keep reopening.

Where this is the wrong call

  • Teams without assigned implementation capacity. Advice with no implementer behind it turns into a document; the fractional seat or a scoped build is the better fit.
  • Organizations that want someone accountable for delivery. Advice is not operating authority, and this engagement does not imply otherwise.
  • Anyone buying presentation polish. The output is decision records and written criteria.
  • Companies with no active AI work and no named business problem. Start with the assessment and stop there if it says to wait.

What happens first

The opening phase, step by step.

The roadmap, build-versus-buy recommendations, decision records, and evaluation criteria are written down. Your leadership retains the decisions and your team retains a repeatable way to examine them.

  • Weeks 1–2

    Retainer start: score what the assessment already found.

    Weeks 1–2 of the retainer follow the assessment; they are not a second inventory billed twice. Each in-scope use case is scored against client-approved value and feasibility criteria. The output includes an explicit stop, defer, or continue recommendation with the reasoning attached.

  • Weeks 3–6

    Decisions, in writing.

    Build-versus-buy on each surviving item, with the criteria recorded so the call can be re-examined when circumstances change. Vendor shortlists, the questions to put to them, and the failure modes to test before anyone signs.

  • Weeks 7–12

    Review and handover of criteria.

    Working sessions move to what your team is actually shipping: data handling, evaluation, deployment path, cost, and monitoring. The evaluation and governance criteria get written down in a form your team can run without me.

Against the alternatives

Advisory, mandate, or visibility.

DimensionAI Visibility MeasurementAI Strategic AdvisorFractional CAIO
Starts withAI Visibility BaselineAI Adoption AssessmentAI Adoption Assessment
Initial termThree-month initial term, then month to monthThree-month initial term, reviewed each quarterSix-month initial term, then month to month
Working cadenceAfter live validation, sampling is planned weekly across configured ChatGPT, Perplexity, Gemini, Claude, and Google AI Mode surfaces, with a written monthly report and review call.A standing weekly working session with the people doing the build, defined async availability between sessions, and a written monthly decision record.A recurring weekly decision cadence, attendance at the leadership meetings named in the mandate, and a written monthly report to the executive team or board.
Scope is set byThe approved question set, validated provider surfaces, locations, competitors, and remediation backlog.The use cases, systems, vendor decisions, stakeholder groups, and risk requirements under review.The decision mandate, leadership cadence, systems in scope, implementation load, vendor portfolio, and risk obligations.
Who holds the mandateYou approve the target questions. I carry responsibility for the measurement process and agreed remediation work.Your leadership holds the mandate. I pressure-test the plan and record the reasoning.I carry the agreed part-time mandate and report on the function.
Decision rightsExecution inside an agreed remediation scope; business decisions stay with you.Advisory. Your leadership decides.Delegated decision rights inside a written mandate; legal, financial, and headcount commitments stay with authorized officers.
Hands on keyboardYes. Profile, schema, and citation work is included within the written scope.Review and working sessions; no implementation in this engagement.Yes, on named systems where separating strategy from delivery would stall the work.
Best forMeasuring and improving how AI answers describe and cite a business.A capable team that needs senior judgment and reusable criteria.An active AI function with no assigned senior mandate and no demonstrated need for a full-time seat yet.

The operator

Who you're working with.

Jeremy Cleland is the sole operator. About gives the background and its limits; Selected Work links the public technical evidence, contribution, status, and limitations.

About JeremyInspect selected work

What this engagement does not include.

Implementation. I review the in-scope code, evaluations, and deployment evidence for documented gaps and failure modes; I do not guarantee where they will break and I do not write the fix. Building requires a fractional mandate that names the implementation or a separately scoped project.

Accountability for delivery. Advisory is not operating authority and this engagement does not imply otherwise. If one person needs to hold the roadmap mandate and answer for the function, that is the fractional seat.

Board slideware. The output is decision records and written criteria. A board conversation can be included in scope to explain the recorded reasoning; presentation production is not implied by the advisory cadence.

Unlimited availability. Availability is defined in the written scope rather than sold as unlimited access. The weekly session, between-session decision channel, systems in view, and response boundaries are named before the engagement starts.

Questions

Asked and answered.

What does an advisory month actually look like?
A standing weekly working session with the people doing the build, agreed availability for decisions between sessions, and a written monthly record of what was decided and what evidence it depends on. The scope names the use cases, systems, and vendor decisions in view so advisory work does not become vague access.
What does the AI Adoption Assessment include?
Over one to two weeks, it produces a use-case inventory scored by value and feasibility, a readiness and governance gap assessment, build-versus-buy guidance, and a prioritized roadmap. The number of stakeholders, systems, use cases, vendors, and risk requirements sets the written scope. The assessment is self-contained whether or not ongoing advisory follows.
Do you write code in this engagement?
No. I review code, evaluations, and the deployment path and document the decisions or failure modes your team needs to address. Building is a separate commitment: either the fractional seat, where implementation can sit inside the mandate, or a separately scoped implementation.
How is this different from the Fractional CAIO mandate?
Decision rights. Here I advise and your leadership decides; accountability for delivery stays with you. In the fractional seat I carry a written part-time mandate, sit in leadership meetings, and report on the function, while legal, financial, and headcount commitments stay with authorized officers. Advisory fits a capable team that needs senior review, not a delegated operating seat.
Can you work with the team rather than only the executives?
Yes. The weekly session is normally run with the engineers and leads doing the work, using the pull requests, evaluations, system plans, and vendor documents already in front of them. The goal is to leave criteria the team can apply without the advisor in the room.
What if the assessment says we should not proceed?
Then the recommendation says so, with the reasons and the conditions that would change the answer. Stopping, narrowing, or deferring work is a legitimate assessment result; the diagnostic does not assume a retainer follows.
Do you cover what happens when the system fails?
Yes. The published AI Contingency Framework's planning phases (1–3) run here, plus a rehearsal plan for your team to execute. I design and review the exercises; I do not run them in this engagement.

Bring the decision you are avoiding.

The fastest way to find out whether this is useful is to put the hardest open question in front of me. If you do not need an advisor, the call should end with that direct recommendation.

Discuss an AI Adoption Assessment (opens in a new tab)