AI-Ready CMO

AI Tool Onboarding Checklist Template

A comprehensive, phase-based checklist for evaluating, selecting, and implementing AI tools across your marketing stack. Use this template to ensure new AI solutions align with business objectives, integrate cleanly, meet compliance requirements, and deliver measurable ROI before, during, and after deployment.

How to Use This Template

  1. 1.## Step 1: Customize the Header and Assign Ownership
  2. 2.**Fill in the tool name, evaluation date, project owner, and target implementation date at the top of the checklist.** This ensures clarity on what's being evaluated, who's driving the decision, and when you need to make a go/no-go call. Assign one person as the primary owner—they'll shepherd the evaluation through all six phases and keep stakeholders aligned. Share this document with your legal, compliance, IT, and marketing leadership teams so everyone knows their role upfront.
  3. 3.## Step 2: Work Through Phase 1 (Strategic Fit) With Your Marketing Team
  4. 4.**Gather your team and complete Phase 1 together, focusing on the business problem and measurable outcomes.** Start by clearly defining what problem this tool solves—don't skip this step. Audit your existing stack to confirm you're not duplicating functionality. Establish 2–3 concrete success metrics (e.g., "reduce content creation time by 40%" or "improve email open rates by 15%") and document your baseline numbers. Identify which tools this new solution must integrate with, and create a rough roadmap with 3 phases and clear milestones. This phase typically takes 1–2 weeks and prevents costly misalignment later.
  5. 5.## Step 3: Evaluate Vendor Reliability and Track Record (Phase 2)
  6. 6.**Request case studies, references, and third-party reviews; contact at least 3 vendor references directly.** Ask references about uptime, responsiveness, and real-world performance—not just feature capability. Check G2 and Capterra ratings, and search for any public outages or service issues. Verify the vendor's uptime guarantee meets your requirement (99.9%+ is standard). Document your findings in the checklist and flag any red flags. This phase takes 2–3 weeks and builds confidence that the vendor will be a reliable partner.
  7. 7.## Step 4: Confirm Legal Compliance and Data Security (Phase 3)
  8. 8.**Work with your legal and compliance teams to review regulatory requirements, request a signed DPA, and confirm data usage policies.** Ensure the vendor is compliant with GDPR, CCPA, or other regulations relevant to your business. Obtain a Data Processing Agreement in writing and have legal review it. Confirm that your data is not shared, resold, or used to train the vendor's AI models—get this in writing. Ask about encryption standards, data storage locations, and backup procedures. This phase is non-negotiable and typically takes 2–4 weeks depending on vendor responsiveness.
  9. 9.## Step 5: Plan Integration and Run a Pilot (Phases 4–5)
  10. 10.**Map technical integrations, schedule training, and run a 4-week pilot with a small team before full rollout.** Identify which systems need to connect (CRM, email, Slack, etc.) and confirm the vendor supports native integrations or provides clear API documentation. Schedule training for your pilot team and create internal documentation. Run the pilot with 3–5 team members on a specific use case, track your success metrics weekly, and collect feedback. Make a clear go/no-go decision based on whether metrics improved and the team is confident. This phase takes 6–8 weeks total.
  11. 11.## Step 6: Execute Full Rollout and Establish Ongoing Monitoring (Phase 6)
  12. 12.**Deploy to your full team, set up performance dashboards, and schedule regular check-ins at 30 days, 90 days, and 6 months.** Ensure all users are trained and support resources (documentation, escalation contacts) are in place. Assign someone to monitor your success metrics weekly or monthly and report findings in a regular cadence (e.g., monthly marketing ops meeting). At 30, 90, and 6-month marks, review actual ROI against your initial goals, identify optimization opportunities, and document lessons learned. This ensures the tool continues to deliver value and informs future tool evaluations.

Template

# AI Tool Onboarding Checklist **Tool Name:** [AI Tool Name] **Evaluation Date:** [Date] **Owner:** [Team Member Name] **Target Implementation Date:** [Date] --- ## Phase 1: Strategic Fit & Problem Definition ### Business Problem & Objectives - [ ] **Define the core problem this tool will solve** - Problem statement: [Describe the specific marketing challenge] - Current impact on business: [Quantify the problem—time lost, revenue impact, etc.] - [ ] **Verify existing tools cannot solve this problem** - Tools already evaluated: [List current solutions] - Why they fall short: [Explain gaps] - Cost of adding features vs. new tool: [Compare] - [ ] **Establish measurable success metrics upfront** - Metric 1: [e.g., reduce content creation time by 40%] - Metric 2: [e.g., improve email open rates by 15%] - Metric 3: [e.g., achieve ROI within 6 months] - Baseline (current state): [Quantify starting point] - [ ] **Confirm tool features match your exact use case** - Required features: [List must-haves] - Nice-to-have features: [List secondary features] - Feature gaps identified: [Note any misalignments] - [ ] **Identify overlaps with current marketing stack** - Current tools in use: [List existing platforms] - Potential redundancies: [Note overlapping functionality] - Integration points needed: [Identify required connections] - [ ] **Create implementation roadmap with clear milestones** - Phase 1 (Weeks 1–2): [Setup and training] - Phase 2 (Weeks 3–6): [Pilot with limited team] - Phase 3 (Weeks 7–12): [Full rollout] - Success checkpoint: [Define go/no-go decision point] --- ## Phase 2: Reliability, Trust & Vendor Assessment ### Vendor Track Record - [ ] **Review detailed case studies relevant to your industry** - Case studies reviewed: [List 3–5 relevant examples] - Similar company size: [ ] Yes [ ] No - Similar use case: [ ] Yes [ ] No - Results achieved: [Summarize outcomes] - [ ] **Request and contact vendor references** - References provided: [ ] Yes [ ] No - Number of references contacted: [e.g., 3 of 5] - Reference feedback summary: [Key takeaways from calls] - Red flags or concerns: [Note any issues raised] - [ ] **Verify uptime and service reliability** - Uptime guarantee: [e.g., 99.9%] - Meets your requirement (99.9%+): [ ] Yes [ ] No - SLA terms: [Summarize] - Penalty/credit policy: [Note compensation for outages] - [ ] **Assess vendor transparency on past outages** - Known outages in past 12 months: [List any] - Duration and impact: [Describe] - Root cause and resolution: [Summarize] - Confidence in vendor response: [ ] High [ ] Medium [ ] Low - [ ] **Review third-party reviews** - G2 rating: [e.g., 4.5/5 stars] - Capterra rating: [e.g., 4.3/5 stars] - Key strengths cited: [List top 3] - Common complaints: [List top 3] - [ ] **Assess vendor responsiveness and partnership quality** - Response time to inquiries: [e.g., <24 hours] - Openness to questions: [ ] Excellent [ ] Good [ ] Needs improvement - Willingness to customize/integrate: [ ] Yes [ ] No [ ] Partial - Account manager assigned: [ ] Yes [ ] No --- ## Phase 3: Legal, Compliance & Data Security ### Regulatory & Data Protection - [ ] **Confirm regulatory compliance** - GDPR compliant: [ ] Yes [ ] No [ ] N/A - CCPA compliant: [ ] Yes [ ] No [ ] N/A - SOC 2 Type II certified: [ ] Yes [ ] No - HIPAA compliant (if applicable): [ ] Yes [ ] No [ ] N/A - Other regulations required: [List any industry-specific requirements] - [ ] **Obtain and review Data Processing Agreement (DPA)** - DPA signed: [ ] Yes [ ] No [ ] In progress - Date signed: [Date] - Legal review completed: [ ] Yes [ ] No - Concerns or modifications needed: [Note any] - [ ] **Understand data storage and encryption practices** - Data storage location(s): [e.g., AWS US-East, EU data centers] - Encryption in transit: [ ] Yes [ ] No - Encryption at rest: [ ] Yes [ ] No - Encryption standard: [e.g., AES-256] - Data backup and recovery process: [Summarize] - [ ] **Verify data usage policies** - Your data is NOT shared with third parties: [ ] Confirmed [ ] Not confirmed - Your data is NOT resold: [ ] Confirmed [ ] Not confirmed - Clear data usage policy in writing: [ ] Yes [ ] No - Policy reviewed by legal/compliance: [ ] Yes [ ] No - [ ] **Confirm data is NOT used for model training** - Vendor uses your data to train AI models: [ ] Yes [ ] No [ ] Unclear - Opt-out available: [ ] Yes [ ] No - Opt-out requested: [ ] Yes [ ] No [ ] N/A - Confirmation in writing: [ ] Yes [ ] No --- ## Phase 4: Integration & Technical Setup ### System Integration & Deployment - [ ] **Map integration requirements** - Systems to integrate with: [e.g., HubSpot, Salesforce, Slack] - Native integrations available: [ ] Yes [ ] No [ ] Partial - API documentation reviewed: [ ] Yes [ ] No - Custom development needed: [ ] Yes [ ] No - Estimated integration time: [e.g., 2 weeks] - [ ] **Plan user access and permissions** - User roles defined: [e.g., Admin, Editor, Viewer] - Number of seats needed: [e.g., 8 users] - SSO/authentication method: [e.g., Okta, Azure AD] - Access provisioning process: [Summarize] - [ ] **Schedule training and onboarding** - Training format: [ ] Live webinar [ ] Self-paced [ ] 1-on-1 [ ] Hybrid - Training date(s): [Schedule] - Attendees: [List team members] - Training materials provided: [ ] Yes [ ] No - Internal documentation created: [ ] Yes [ ] No --- ## Phase 5: Pilot & Performance Validation ### Limited Rollout & Testing - [ ] **Define pilot scope and timeline** - Pilot team size: [e.g., 3 team members] - Pilot duration: [e.g., 4 weeks] - Pilot use cases: [List specific workflows to test] - Success criteria: [Define what "success" looks like] - [ ] **Monitor pilot performance against baseline metrics** - Metric 1 baseline: [Starting value] - Metric 1 target: [Goal] - Metric 1 actual result: [Pilot result] - Metric 2 baseline: [Starting value] - Metric 2 target: [Goal] - Metric 2 actual result: [Pilot result] - [ ] **Collect pilot team feedback** - Feedback method: [ ] Survey [ ] Interviews [ ] Focus group - Key feedback themes: [Summarize] - Issues encountered: [List any problems] - Recommended improvements: [Note suggestions] - [ ] **Make go/no-go decision** - Metrics met: [ ] Yes [ ] No [ ] Partially - Team readiness: [ ] Yes [ ] No [ ] Needs more training - Technical issues resolved: [ ] Yes [ ] No [ ] Minor issues remain - **Decision: [ ] Proceed to full rollout [ ] Extend pilot [ ] Do not proceed** - Decision rationale: [Explain reasoning] --- ## Phase 6: Full Rollout & Ongoing Management ### Deployment & Continuous Improvement - [ ] **Execute full team rollout** - Rollout date: [Date] - All users trained: [ ] Yes [ ] No - Support resources in place: [ ] Yes [ ] No - Escalation process documented: [ ] Yes [ ] No - [ ] **Establish ongoing performance monitoring** - Monitoring frequency: [e.g., weekly, monthly] - Owner responsible for tracking: [Name] - Dashboard/reporting tool: [e.g., custom spreadsheet, BI tool] - Review meeting cadence: [e.g., monthly] - [ ] **Schedule regular check-ins and optimization** - 30-day check-in: [Date] - 90-day review: [Date] - 6-month ROI assessment: [Date] - Optimization opportunities identified: [List any] - [ ] **Document lessons learned** - What worked well: [Summarize] - What could be improved: [Summarize] - Recommendations for future tool evaluations: [Note] - Knowledge base/wiki updated: [ ] Yes [ ] No --- ## Sign-Off | Role | Name | Date | Approval | |------|------|------|----------| | Project Owner | [Name] | [Date] | [ ] Approved | | Marketing Leader | [Name] | [Date] | [ ] Approved | | Compliance/Legal | [Name] | [Date] | [ ] Approved | | IT/Technical Lead | [Name] | [Date] | [ ] Approved | **Notes & Comments:** [Add any additional context or outstanding items]

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Courses, workshops, frameworks, daily intelligence, and 6 proprietary tools — built for marketing leaders adopting AI.

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