Illustrative — tailored per engagement after discovery.
This plan launches Claude Enterprise as a horizontal capability for white-collar employees while identifying and sequencing three future capability tracks: support agent assist, BI and analytics Q&A, and director planning copilot. The first 30 days focus on technical setup, governance, controlled connector enablement, and one live pilot, with an explicit backlog for larger workflow-redesign opportunities discovered during rollout.
Timeline and workstreams
The AI Strategy Advisor participates in every phase; the owners listed are the client-side leads.
Days 1–3 · Launch charter
- Owners
- Head of Technology · HR Director · Legal Director · Security/Compliance Director · RevOps Director
- Advisor role
- Lead structured discovery, frame decision points, and convert executive goals into a launch charter and phase logic.
- Primary work
- Confirm steering committee, approve launch scope, define 30-day success criteria, identify Pilot 1, and approve a conservative initial risk posture.
- Advisor deliverables
- Discovery agenda, decision log, draft launch charter, initial pilot recommendation, and success-metric framework.
- Team deliverables
- Signed launch charter, pilot selection, success metrics, and decision log.
- Handoff
- Advisor hands approved charter, decision log, and open questions to technical, policy, and enablement workstreams.
Days 1–5 · Identity & access
- Owners
- Head of Technology · IT/Identity lead
- Advisor role
- Advise on deployment model, access-group design, and control implications of identity choices; review whether the identity model supports later scale.
- Primary work
- Configure Claude Enterprise tenant basics and SSO through the client's identity provider (e.g., Entra ID, Okta), with SCIM directory sync for automated provisioning and deprovisioning — including group-to-role mappings so access is managed through existing corporate identity groups. Dependency: assumes IdP admin availability in week 1, confirmed during the charter.
- Advisor deliverables
- Identity and access design memo, recommended group structure, and implementation review checklist.
- Team deliverables
- Working SSO, group design, provisioning rules, and initial user tiers.
- Handoff
- Identity setup is handed to Security and app admins for access validation, with advisor review of unresolved access-model issues.
Days 2–7 · Governance & policy
- Owners
- Legal Director · Security/Compliance Director · Head of Technology
- Advisor role
- Translate enterprise AI governance best practice into client-specific policy language, review acceptable use and risk tiers, and pressure-test whether the controls are usable in practice.
- Primary work
- Finalize acceptable-use policy, data-handling rules for PII and company secrets, initial retention and logging rules, and the launch risk-tiering matrix.
- Advisor deliverables
- Governance framework, acceptable-use policy draft inputs, risk-tiering recommendations, and escalation-model proposal.
- Team deliverables
- Approved policy pack: acceptable use, risk matrix, escalation path, and audit expectations.
- Handoff
- Policy pack is handed to pilot owners, training lead, and technical team for implementation, with advisor documenting policy assumptions and later relaxation criteria.
Days 3–10 · Knowledge & connectors
- Owners
- Head of Technology · Knowledge systems owner · IT/Data lead
- Advisor role
- Define the source-enablement priority order, connector governance principles, and read/write scoping by role and data sensitivity.
- Primary work
- Enable and govern Claude Enterprise's native connectors for approved repositories — document repositories first (e.g., SharePoint via the Microsoft 365 connector), then wikis (e.g., Confluence), then code documentation (e.g., GitHub) — configured read-only at launch. Connectors are enabled at the organization level and users authenticate individually, so access rides existing repository permissions rather than a parallel index. Validate permission inheritance with test accounts across sensitivity levels before pilot users touch it. Custom retrieval (remote MCP) is explicitly deferred: a Wave 2 decision, only for required sources with no native connector.
- Advisor deliverables
- Connector strategy note, source-prioritization rationale, read/write scoping recommendations, and permission-validation test plan.
- Team deliverables
- Pilot-ready connected sources, source inventory, access-validation results, and connector configuration record.
- Handoff
- Connected sources are handed to the Pilot 1 owner for testing and prompt/workflow design, with advisor validating that read/write scoping matches intended business use.
Days 5–12 · Pilot 1 design
- Owners
- Pilot 1 business owner · Head of Technology · selected pilot users
- Advisor role
- Lead pilot framing, define the business question the pilot is meant to answer, and shape model-routing, review, and measurement logic.
- Primary work
- Design the Pilot 1 workflow, prompt patterns, human-review checkpoints, model-routing rules, and measurable before/after baseline metrics.
- Advisor deliverables
- Pilot strategy brief, workflow design recommendations, KPI framework, and go/no-go criteria.
- Team deliverables
- Pilot runbook, approved prompts, QA checklist, and KPI baseline.
- Handoff
- Pilot runbook is handed to enablement for training and to Security for final launch review, with advisor confirming the business-value hypothesis and measurement design.
Days 8–15 · Training & enablement
- Owners
- HR Director · enablement/training lead · Head of Technology
- Advisor role
- Shape training around real workflows and risk posture, ensuring the program teaches both safe use and value creation rather than generic AI literacy alone.
- Primary work
- Prepare role-based training, launch communications, office hours, and a short internal playbook for safe usage and escalation.
- Advisor deliverables
- Training strategy, role-based curriculum outline, leader talking points, and usage-guidance inputs.
- Team deliverables
- User training deck, quick-start guide, FAQ, and launch communications.
- Handoff
- Training assets are handed to managers and pilot champions for distribution, with advisor reviewing whether materials match the actual approved workflows and controls.
Days 12–20 · Pilot 1 launch & monitoring
- Owners
- Pilot 1 owner · Head of Technology · Security/Compliance Director
- Advisor role
- Monitor pilot behavior, synthesize issues, distinguish execution noise from structural problems, and capture redesign opportunities surfaced by real use.
- Primary work
- Launch Pilot 1 to a controlled group, monitor usage, review output quality, and capture incidents, blockers, and redesign opportunities in a centralized backlog.
- Advisor deliverables
- Pilot observation memo, issue synthesis, redesign backlog, and interim recommendation set.
- Team deliverables
- Live pilot, daily issue log, and redesign-opportunity backlog.
- Handoff
- Findings are handed to the steering committee for go/no-go and scope-expansion decisions, with advisor presenting the interpretation and recommended actions.
Days 18–25 · Expansion decision
- Owners
- Head of Technology · RevOps Director · Security/Compliance Director
- Advisor role
- Lead the decision review on what to expand, what to tighten, and what to postpone; convert pilot evidence into next-wave strategy.
- Primary work
- Review adoption, quality, and risk data; decide which controls can be relaxed, which user groups expand next, and what the next two pilots require. Score the three candidate capability tracks — support agent assist, BI/analytics Q&A, and director planning copilot — against pilot evidence to sequence Wave 2.
- Advisor deliverables
- Expansion decision memo, control-adjustment recommendations, and wave-2 strategy draft.
- Team deliverables
- Expansion recommendation, updated controls, and wave-2 rollout list.
- Handoff
- Steering committee approves revised guardrails and next-wave deployment, using the advisor memo as the principal recommendation artifact.
Days 25–30 · Executive readout
- Owners
- Head of Technology · all directors
- Advisor role
- Own the synthesis of the first 30 days into an executive readout and next-cycle plan; articulate what was learned, what changed, and what should happen next.
- Primary work
- Publish the post-launch readout covering adoption, incidents, KPI movement, policy changes, and the ranked redesign backlog for follow-on prioritization.
- Advisor deliverables
- Executive readout, updated rollout plan, prioritized redesign backlog, and phase-2 advisory recommendation.
- Team deliverables
- 30-day readout, updated rollout plan, and wave-2 implementation brief.
- Handoff
- Readout becomes the operating baseline for the next 30-day cycle, with advisor recommendations informing the next statement of work or extension.
Roles and responsibilities
- AI Strategy Advisor
- Owns the model-first structure of the engagement, facilitates executive decisions, translates requirements into rollout strategy, pressure-tests governance and architecture choices, shapes pilot design, and synthesizes findings into next-step recommendations.
- Head of Technology
- Accountable for overall rollout, internal decision velocity, architecture sign-off, pilot prioritization, and final executive sponsorship of the program.
- HR Director
- Owns training coordination, manager communications, adoption support, and employee-facing usage guidance.
- Legal Director
- Owns acceptable-use language, review thresholds for sensitive workflows, and policy sign-off for customer-visible or regulated outputs.
- Security/Compliance Director
- Owns identity and access approval, data-handling controls, logging and retention decisions, and incident review.
- RevOps Director
- Owns business-value measurement for revenue and support-adjacent workflows and helps prioritize redesign opportunities.
- Pilot business owner
- Owns workflow design inputs, user feedback, local operational adoption, and business accountability for pilot success measures.
Advisor deliverables by stage
The AI Strategy Advisor is not just present as a meeting facilitator; the role produces explicit decision artifacts at each stage so the client can move from ambiguity to action. The expected deliverables are: launch charter and decision log; identity and access design memo; governance framework and policy inputs; connector strategy note; pilot strategy brief; training strategy; pilot observation memo; expansion decision memo; and final executive readout with updated rollout recommendations.
Coordination model
Work proceeds in parallel across four coordinated tracks — governance, identity/security, knowledge/connectors, and pilot enablement — with the AI Strategy Advisor acting as the cross-stream integrator who keeps the effort aligned to business intent rather than letting it fragment into isolated technical tasks.
The required handoffs are simple: policy decisions must arrive before pilot launch, identity groups must exist before connector permissions are validated, and the pilot runbook must be complete before training goes live. A 30-minute twice-weekly operating review is enough for synchronization if every workstream brings decisions needed, deliverables completed, blockers, and next handoffs.