AI-Ready CMO

Product-Led Growth Strategy Assessment Framework

Marketing StrategyadvancedClaude 3.5 Sonnet or GPT-4o. Claude excels at structured strategic analysis and nuanced risk assessment; GPT-4o is faster for iterative refinement. For this advanced assessment, Claude's reasoning depth is preferred for the first run, then GPT-4o for rapid follow-up iterations.

When to Use This Prompt

Use this prompt when you're evaluating whether to shift toward a product-led growth model or optimize an existing PLG motion. It's ideal for CMOs facing sales efficiency challenges, high CAC, or market pressure to improve self-serve conversion. Run this assessment quarterly to identify where operational debt is hiding revenue and where AI-driven automation can unlock faster user progression.

The Prompt

You are a strategic marketing advisor specializing in product-led growth (PLG) assessment for B2B SaaS companies. Your task is to conduct a comprehensive PLG readiness audit for [COMPANY_NAME], a [COMPANY_DESCRIPTION] with [ANNUAL_REVENUE] in ARR and [CUSTOMER_COUNT] customers. ## Current State Assessment Analyze the following aspects of our current go-to-market: **Product & Monetization:** - Current pricing model: [PRICING_MODEL] - Free tier/trial structure: [TRIAL_STRUCTURE] - Primary conversion bottleneck: [CONVERSION_BOTTLENECK] - Average time from signup to paid conversion: [CONVERSION_TIME] **User Experience & Onboarding:** - Current onboarding flow: [ONBOARDING_DESCRIPTION] - Time to first value (TTFV): [TTFV_DAYS] - Activation rate (% reaching key milestone): [ACTIVATION_RATE] - Churn rate for free users: [FREE_CHURN_RATE] **Go-to-Market Motion:** - Current sales model: [SALES_MODEL] (e.g., fully self-serve, hybrid, sales-assisted) - Sales team size: [SALES_TEAM_SIZE] - CAC: [CAC_AMOUNT] - LTV: [LTV_AMOUNT] - LTV:CAC ratio: [LTV_CAC_RATIO] **Operational Friction:** - Key workflow bottlenecks slowing user progression: [BOTTLENECK_1], [BOTTLENECK_2], [BOTTLENECK_3] - Tools creating coordination overhead: [TOOLS_LIST] - Approval processes delaying feature/content deployment: [APPROVAL_PROCESSES] ## Strategic Assessment Framework Provide a detailed assessment across these dimensions: 1. **PLG Readiness Score** (1-10 scale with rationale) - Product maturity for self-serve - Monetization alignment with PLG model - Organizational readiness - Market fit indicators 2. **High-Friction Workflow Audit** - Identify the single highest-leverage workflow where time is leaking and revenue is at stake - Quantify the impact (time saved, conversion lift potential, revenue impact) - Assess operational debt in this workflow 3. **Immediate Wins (30-90 days)** - Three specific, measurable initiatives to improve PLG metrics - Expected impact on activation, conversion, or expansion - Resource requirements and implementation complexity 4. **Scaling Roadmap (6-12 months)** - Phase 1: Foundation (what must be true first) - Phase 2: Acceleration (leverage early wins) - Phase 3: Expansion (new user segments or use cases) - Success metrics for each phase 5. **Risk Assessment** - Organizational risks (sales team resistance, channel conflict) - Product risks (insufficient self-serve capability) - Market risks (competitive positioning, buyer behavior) - Mitigation strategies for each ## Output Requirements Structure your response as: - Executive Summary (2-3 sentences on overall PLG fit) - Detailed Assessment (address each framework section) - Prioritized Action Plan (ranked by impact and feasibility) - Success Metrics Dashboard (KPIs to track progress) - Governance Recommendations (lightweight rules to avoid missteps)

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Tips for Best Results

  • 1.Replace all [BRACKETS] with specific, quantified data. Vague inputs (e.g., 'high churn') produce generic outputs. Use actual metrics: activation rates, TTFV in days, CAC in dollars.
  • 2.Run this prompt twice: first with current-state data, then with 'ideal-state' assumptions to see the gap. This reveals which metrics are most constraining your PLG potential.
  • 3.Ask follow-up prompts for specific phases: 'Expand Phase 1 into a detailed 90-day sprint plan' or 'Create a sales enablement playbook for the hybrid motion.' Compound the initial assessment.
  • 4.Use the output to audit operational debt in your actual workflows. The prompt identifies friction; your job is validating it with your team and quantifying the cost of each bottleneck.

Example Output

## Executive Summary TechFlow shows strong PLG potential with a mature product and clear self-serve capability, but operational debt in onboarding and activation workflows is suppressing conversion lift. Estimated 25-35% improvement in activation rate is achievable within 90 days by streamlining the first-value experience and reducing approval cycles for content deployment. ## PLG Readiness Score: 7.2/10 **Product Maturity (8/10):** Feature-rich, intuitive interface, clear value prop. Minor gaps in contextual guidance for advanced workflows. **Monetization Alignment (6.5/10):** Pricing model supports self-serve, but free tier is too generous—users delay conversion. Expansion revenue potential underdeveloped. **Organizational Readiness (7/10):** Marketing and product aligned; sales team concerns about channel conflict need proactive management. **Market Fit (7.5/10):** Target buyer (mid-market ops teams) self-educates and prefers self-serve trials. Competitive landscape rewards speed to value. ## High-Friction Workflow Audit **Highest-Leverage Opportunity:** Onboarding-to-activation workflow - Current state: 14-day average TTFV; 32% activation rate - Friction points: Generic email sequence (no personalization), manual setup required, no in-app guidance - Revenue impact: 8-point activation lift = ~$180K additional ARR annually - Operational debt: 40 hours/month spent on manual onboarding support ## Immediate Wins (30-90 days) **1. AI-Powered Contextual Onboarding (Impact: +6-8 activation points)** - Deploy in-app guidance engine triggered by user behavior, not generic sequence - Reduce TTFV from 14 days to 7 days - Effort: 3 weeks; requires product and marketing collaboration **2. Streamline Free-to-Paid Conversion Flow (Impact: +4-5 conversion points)** - Remove 3-step approval process for trial-to-paid upgrade prompts - A/B test pricing presentation and timing - Effort: 2 weeks; marketing and legal alignment **3. Automate Expansion Revenue Triggers (Impact: +12% net revenue retention)** - Identify usage patterns signaling readiness for higher-tier features - Deploy automated in-app upsell prompts with education content - Effort: 4 weeks; requires analytics and product engineering ## Scaling Roadmap (6-12 months) **Phase 1 (Months 1-3): Foundation** - Implement contextual onboarding and streamlined conversion flow - Establish lightweight governance (brand, security, data guardrails) - Target: 40% activation rate, 18% free-to-paid conversion **Phase 2 (Months 4-6): Acceleration** - Launch expansion revenue automation - Build community/peer learning features to drive viral adoption - Introduce self-serve analytics dashboard for power users - Target: 50% activation, 22% conversion, 125% NRR **Phase 3 (Months 7-12): Expansion** - Develop vertical-specific onboarding paths - Launch API-first integrations to reduce setup friction - Build customer-led content strategy (case studies, templates) - Target: 55% activation, 25% conversion, 135% NRR ## Success Metrics Dashboard - Activation Rate: Current 32% → Target 55% (Phase 3) - Time to First Value: Current 14 days → Target 5 days - Free-to-Paid Conversion: Current 18% → Target 25% - CAC: Current $8,500 → Target $6,200 (through self-serve efficiency) - LTV:CAC Ratio: Current 2.8x → Target 4.2x - Net Revenue Retention: Current 110% → Target 135% - Operational Overhead: Reduce onboarding support hours by 60% ## Governance Recommendations - Establish a lightweight PLG steering committee (marketing, product, sales, legal) meeting bi-weekly - Create a simple approval matrix for user-facing changes (brand, messaging, pricing) - Implement a 48-hour deployment window for non-breaking changes - Quarterly audit of operational debt in key workflows

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

Trusted by 10,000+ Directors and CMOs.