dojo.md 0.1.0

package/courses/upsell-cross-sell-recommendations/scenarios/level-5/comprehensive-expansion-engagement.yaml

@@ -0,0 +1,87 @@
+meta:
+  id: comprehensive-expansion-engagement
+  level: 5
+  course: upsell-cross-sell-recommendations
+  type: output
+  description: "Lead a comprehensive expansion transformation — integrate all expansion disciplines into a cohesive capability that makes customer expansion the primary growth engine and competitive moat"
+  tags: [sales, upsell, cross-sell, comprehensive, transformation, growth-engine, master]
+
+state: {}
+
+trigger: |
+  You've been hired as the first Chief Growth Officer (CGO) at
+  "NexGenSaaS" ($1B ARR, targeting $3B in 5 years). The CEO created
+  this role specifically to make customer expansion the company's
+  primary competitive advantage. Your mandate: build a world-class
+  expansion function that produces 60% of all growth (currently 25%).
+
+  Starting position:
+  - $1B ARR, 12,000 customers, 40 countries
+  - NRR: 108% (target: 130%+ within 3 years)
+  - Expansion as % of growth: 25% (target: 60%)
+  - Expansion team: 45 people (scattered across CS, Sales, Ops)
+  - No unified expansion strategy, no AI, no customer marketing
+  - Average expansion deal size: $35K
+  - Expansion close rate: 25%
+  - Estimated annual value leakage: $300M
+
+  Your budget: $25M over 3 years
+  Your headcount authority: 0 → 120+ (expansion team)
+
+  CEO's vision:
+  "In 3 years, I want analysts to cite our expansion capability as
+  the reason to buy our stock. I want customers to expand because our
+  experience is so good they naturally want more. I want competitors
+  to study our expansion playbook. And I want to capture $200M of the
+  $300M we're currently leaking."
+
+  The challenge:
+  Simultaneously build 10 capabilities:
+  1. Expansion strategy and playbook
+  2. Expansion organization (team, roles, structure)
+  3. Expansion analytics and AI
+  4. Product-led expansion
+  5. Customer marketing for expansion
+  6. Partner expansion program
+  7. Executive sponsor program
+  8. Expansion compensation alignment
+  9. Global expansion standardization
+  10. Expansion thought leadership and category creation
+
+  Tasks:
+  1. Write the "CGO 100-Day Plan" — your first 100 days. Days 1-30:
+     Assessment and quick wins. Days 31-60: Strategy and design.
+     Days 61-100: Launch and early wins. Include deliverables, key
+     hires, stakeholder engagement, and first metrics report.
+
+  2. Write the "3-Year Expansion Transformation Roadmap" — the
+     comprehensive plan. Year 1: Foundation (org build, playbook, tech,
+     basic analytics). Year 2: Acceleration (AI, customer marketing,
+     global scaling, partner program). Year 3: Excellence (predictive
+     models, category leadership, public company optimization). For
+     each year: initiatives, budget, headcount, technology, expected
+     NRR and expansion revenue impact, and risks.
+
+  3. Write the "Competitive Moat Thesis" — how expansion capability
+     becomes an unassailable competitive advantage. Include: the
+     customer experience advantage, the data advantage (12,000 accounts
+     of expansion data creates AI superiority), the talent advantage
+     (top expansion talent wants to work at the best), the ecosystem
+     advantage (partners and marketplace amplify expansion), the brand
+     advantage (thought leadership establishes authority), and the
+     financial advantage (expansion economics fund more expansion
+     investment, creating a virtuous cycle).
+
+assertions:
+  - type: llm_judge
+    criteria: "100-day plan builds CGO credibility — assessment, design, and launch phases with quick wins, key hires, and metrics that establish the expansion function"
+    weight: 0.35
+    description: "Credibility-building 100-day plan"
+  - type: llm_judge
+    criteria: "3-year roadmap transforms at scale — 10 capabilities built across 3 phases with budget, headcount, technology, NRR projections, and risks for a $1B company"
+    weight: 0.35
+    description: "Scale-appropriate transformation roadmap"
+  - type: llm_judge
+    criteria: "Competitive moat thesis is compelling — customer experience, data, talent, ecosystem, brand, and financial advantages that create a defensible expansion capability"
+    weight: 0.30
+    description: "Compelling competitive moat thesis"

package/courses/upsell-cross-sell-recommendations/scenarios/level-5/expansion-ai-future.yaml

@@ -0,0 +1,111 @@
+meta:
+  id: expansion-ai-future
+  level: 5
+  course: upsell-cross-sell-recommendations
+  type: output
+  description: "Architect the future of AI-native expansion — design a next-generation expansion system where AI autonomously identifies, nurtures, and closes expansion opportunities with minimal human intervention"
+  tags: [sales, upsell, cross-sell, AI, autonomous, future, innovation, master]
+
+state: {}
+
+trigger: |
+  You've been hired as the "Head of AI-Native Expansion" at "FutureSaaS"
+  ($2B ARR, 25,000 customers). The CEO wants to build the world's first
+  fully AI-native expansion function — where AI doesn't just assist
+  humans but autonomously runs 80% of the expansion process. The vision:
+  reduce the expansion team from 200 humans to 40 human strategists
+  supported by AI systems, while tripling expansion revenue from $240M
+  to $720M annually.
+
+  Current state:
+  - 200-person expansion team (AMs, CSMs, expansion specialists)
+  - $240M expansion ARR (12% of base)
+  - NRR: 115%
+  - Average expansion cycle: 45 days
+  - Expansion close rate: 28%
+  - Human cost of expansion team: $32M/year
+  - Tools: Salesforce, Gainsight, Gong, custom dashboards
+
+  AI-native vision (3-year horizon):
+  - AI identifies 95% of expansion opportunities autonomously
+  - AI personalizes and sends 80% of expansion communications
+  - AI negotiates pricing for deals under $50K
+  - AI predicts expansion timing with 85%+ accuracy
+  - AI generates custom proposals, ROI models, and business cases
+  - AI manages the full expansion pipeline and forecasts NRR
+  - Humans focus on strategic accounts ($500K+), relationship building,
+    and complex multi-stakeholder negotiations
+
+  Technology landscape available:
+  - Foundation models (GPT-5, Claude 4, Gemini Ultra) for reasoning
+  - Agent frameworks for autonomous workflow execution
+  - Real-time product telemetry (500M events/day)
+  - Behavioral analytics across 25,000 accounts
+  - NLP for conversation intelligence across 2M annual interactions
+  - Computer vision for product usage pattern recognition
+  - Reinforcement learning for pricing optimization
+
+  Constraints:
+  - Budget: $15M over 3 years (must show positive ROI by month 18)
+  - Enterprise customers require human touchpoints for deals over $100K
+  - Regulatory considerations in healthcare (HIPAA) and finance (SOX)
+  - Change management: 200-person team will resist automation
+  - Data privacy: EU customers subject to AI Act requirements
+  - Board skepticism: "AI replacing salespeople" narrative is risky
+
+  Tasks:
+  1. Write the "AI-Native Expansion Architecture" — the technical and
+     organizational blueprint. Include: the AI expansion stack (which AI
+     capabilities handle which parts of the expansion process — signal
+     detection, opportunity scoring, communication, proposal generation,
+     negotiation, closing), the human-AI collaboration model (where
+     humans remain essential and how they work alongside AI agents), the
+     data architecture (how 500M daily events, conversation data, and
+     behavioral analytics feed the AI systems), the autonomous expansion
+     agent design (how AI agents operate independently — their decision
+     boundaries, escalation triggers, and self-improvement loops), the
+     ethics and governance framework (preventing AI from being
+     manipulative, ensuring transparency with customers, handling the
+     "AI sold me something I don't need" scenario), and the phased
+     rollout (which expansion segments go AI-first and in what order).
+
+  2. Write the "Workforce Transformation Plan" — how to transition 200
+     humans to 40 AI-augmented strategists. Include: the skills
+     assessment (which current team members can become AI-augmented
+     strategists), the reskilling program (training humans to work with
+     AI — prompt engineering, AI oversight, exception handling, strategic
+     relationship management), the organizational redesign (new roles:
+     AI expansion strategist, expansion AI trainer, expansion data
+     scientist, expansion ethics officer), the change management
+     strategy (how to frame this as augmentation not replacement), the
+     retention plan for top performers (how to keep the best 40 while
+     transitioning 160), and the timeline with milestones (quarterly
+     transitions over 2 years with off-ramps if AI performance falls
+     short).
+
+  3. Write the "AI Expansion Economics Model" — the financial case for
+     AI-native expansion. Include: the current cost structure ($32M
+     human cost, $8M tools, $240M expansion revenue = 16.7% cost of
+     expansion), the target cost structure ($6M human cost, $15M AI
+     infrastructure amortized, $720M expansion revenue = 2.9% cost of
+     expansion), the transition economics (costs, savings, and revenue
+     impact for each quarter over 3 years), the risk-adjusted projections
+     (scenarios where AI performs at 60%, 80%, and 100% of target), the
+     competitive impact (what happens if competitors build this first
+     vs second-mover advantage of learning from their mistakes), and
+     the valuation impact (how AI-native expansion changes the company's
+     growth narrative and multiple — from 8x to 15x ARR potential).
+
+assertions:
+  - type: llm_judge
+    criteria: "AI architecture is visionary yet grounded — AI stack, human-AI collaboration, data architecture, autonomous agent design, ethics framework, and phased rollout for a $2B ARR company"
+    weight: 0.35
+    description: "Visionary yet grounded AI architecture"
+  - type: llm_judge
+    criteria: "Workforce transformation is humane and practical — skills assessment, reskilling, organizational redesign, change management, retention, and timeline for 200→40 transition"
+    weight: 0.35
+    description: "Humane workforce transformation plan"
+  - type: llm_judge
+    criteria: "Economics model justifies investment — current vs target cost structure, transition economics, risk-adjusted projections, competitive impact, and valuation impact from 16.7% to 2.9% cost of expansion"
+    weight: 0.30
+    description: "Investment-justifying economics model"

package/courses/upsell-cross-sell-recommendations/scenarios/level-5/expansion-board-strategy.yaml

@@ -0,0 +1,85 @@
+meta:
+  id: expansion-board-strategy
+  level: 5
+  course: upsell-cross-sell-recommendations
+  type: output
+  description: "Present expansion strategy to the board — build the board-level narrative on how expansion capability drives valuation, competitive moat, and sustainable growth"
+  tags: [sales, upsell, cross-sell, board, valuation, strategy, governance, master]
+
+state: {}
+
+trigger: |
+  You're the CEO of "ValueMax" ($600M ARR, targeting $2B+ IPO in 18
+  months). Your board has requested a comprehensive presentation on how
+  your expansion strategy will drive the valuation they expect. Current
+  NRR of 112% is good but not the 125%+ that commands a premium multiple.
+
+  Board context:
+  - Target IPO valuation: $6B (10x ARR)
+  - Current implied valuation at 112% NRR: $4.8B (8x ARR)
+  - Target valuation at 125% NRR: $7.2B (12x ARR)
+  - Valuation gap: $2.4B — driven primarily by NRR
+
+  Financial data:
+  - $600M ARR, growing 30% YoY
+  - Expansion ARR: $72M/year (12% of base)
+  - Gross churn: 7%
+  - NRR: 112%
+  - Expansion as % of new ARR: 40%
+  - Customer lifetime: 5.8 years average
+  - Expansion CAC: $11K (vs new business CAC: $58K)
+  - Rule of 40: 38% (30% growth + 8% margin)
+
+  Competitive intelligence:
+  - Competitor A: NRR 128%, valued at 15x ARR
+  - Competitor B: NRR 122%, valued at 12x ARR
+  - Competitor C: NRR 115%, valued at 9x ARR
+  - The NRR-to-multiple correlation is clear
+
+  Board members:
+  - 3 growth equity directors (focused on growth rate and efficiency)
+  - 2 independent directors (risk-averse, governance-focused)
+  - CFO (IPO-focused, investor relations)
+  - CEO (you — presenting)
+
+  Tasks:
+  1. Write the "Board Presentation" — 12 slides. Include: the
+     strategic imperative (why NRR is the key to valuation), the
+     current assessment (where we are, honest gaps), the competitive
+     benchmarking (how NRR correlates with multiples), the
+     transformation plan (how we go from 112% to 125%+), the
+     investment case (what we need to spend), the financial projections
+     (3-year ARR under different NRR scenarios), the risk assessment,
+     and the specific ask (budget approval and governance framework).
+
+  2. Write the "Investor Narrative on Expansion" — how expansion
+     becomes a key part of the IPO story. Include: the NRR as
+     competitive moat narrative, the efficient growth narrative (how
+     expansion improves unit economics), the platform expansion
+     narrative (how product evolution drives expansion), the market
+     expansion narrative (how geographic and vertical expansion
+     contribute), and the durability narrative (why your expansion
+     rate is sustainable, not temporary).
+
+  3. Write the "Board Governance Framework for Expansion" — how the
+     board oversees the expansion transformation. Include: the
+     quarterly reporting package (metrics, commentary, risks), the
+     delegation framework (what management decides vs board approves),
+     the investment triggers (when additional investment is warranted),
+     the risk limits (maximum acceptable exposure from expansion
+     investments), and the success criteria (how the board evaluates
+     whether the strategy is working).
+
+assertions:
+  - type: llm_judge
+    criteria: "Board presentation connects NRR to valuation — 12 slides with strategic imperative, honest assessment, competitive benchmarks, and financial projections showing the $2.4B valuation gap"
+    weight: 0.35
+    description: "Valuation-connecting board presentation"
+  - type: llm_judge
+    criteria: "Investor narrative is IPO-ready — competitive moat, efficient growth, platform expansion, market expansion, and durability narratives that investors would find compelling"
+    weight: 0.35
+    description: "IPO-ready investor narrative"
+  - type: llm_judge
+    criteria: "Governance framework enables oversight — quarterly reporting, delegation, investment triggers, risk limits, and success criteria for board-level expansion governance"
+    weight: 0.30
+    description: "Oversight-enabling governance framework"

package/courses/upsell-cross-sell-recommendations/scenarios/level-5/expansion-category-creation.yaml

@@ -0,0 +1,91 @@
+meta:
+  id: expansion-category-creation
+  level: 5
+  course: upsell-cross-sell-recommendations
+  type: output
+  description: "Create a new category around expansion — position your company as the definitive leader in 'customer expansion intelligence' by creating and owning a new market category"
+  tags: [sales, upsell, cross-sell, category-creation, positioning, market, master]
+
+state: {}
+
+trigger: |
+  You're the CEO of "ExpansionIQ" — a startup ($15M ARR, Series B)
+  that has built an AI-powered platform specifically for identifying,
+  prioritizing, and executing customer expansion opportunities. You
+  compete in the "customer success platform" category against Gainsight,
+  ChurnZero, Totango, and others. But your investors and board believe
+  you should create and own a new category: "Customer Expansion
+  Intelligence."
+
+  Why category creation:
+  - Customer success platforms focus on retention (preventing churn)
+  - Your platform focuses on growth (driving expansion)
+  - The CS platform market is commoditizing (features converging)
+  - Analysts group you with CS platforms, which limits your valuation
+  - A new category would position you as the leader, not a follower
+
+  Your differentiation:
+  - AI-powered expansion signal detection (no CS platform has this)
+  - Predictive NRR modeling (unique capability)
+  - Expansion-optimized pricing recommendations
+  - Cross-sell intelligence from product usage data
+  - Expansion pipeline management (purpose-built, not CRM adapted)
+
+  Market data:
+  - CS platform market: $2.5B, growing 18% YoY
+  - Estimated "expansion intelligence" market: $800M (subset of CS +
+    RevOps + product analytics markets)
+  - Potential market in 5 years: $4B (as companies shift focus from
+    retention to expansion)
+  - Your current market share of CS platforms: 0.6%
+  - Your potential market share of expansion intelligence: 15-20%
+
+  Category creation requirements:
+  1. Define the category (what it is, what it isn't)
+  2. Establish the problem (why existing categories fail)
+  3. Position yourself as the obvious leader
+  4. Get analysts, press, and customers to use the term
+  5. Build a community around the category
+
+  Tasks:
+  1. Write the "Category Definition Document" — the foundational
+     document that defines Customer Expansion Intelligence. Include:
+     the category name and definition, the problem statement (why
+     existing tools fail at expansion), the buyer persona (who buys
+     this, what title, what budget), the category landscape (who else
+     could be in this category and how you differ), the evaluation
+     criteria (what buyers should look for when evaluating solutions
+     in this category), and the market sizing (current and projected).
+
+  2. Write the "Category Creation Go-to-Market Plan" — how to launch
+     and establish the category. Include: the analyst relations strategy
+     (how to get Gartner/Forrester to recognize the category), the
+     content strategy (thought leadership that educates the market),
+     the community building plan (events, user groups, industry
+     association), the customer advocacy program (getting customers
+     to evangelize the category), the PR strategy (media placements,
+     speaking engagements, awards), and the competitive positioning
+     (how to handle existing CS platforms' inevitable response).
+
+  3. Write the "Category Economics Thesis" — the financial argument
+     for why this category deserves investment. Include: the market
+     creation opportunity ($800M → $4B), the category leader economics
+     (why the category creator captures disproportionate value), the
+     valuation impact (category leaders trade at premium multiples),
+     the customer acquisition advantage (category leader = default
+     choice), and the competitive moat (why followers can't easily
+     replicate the category leadership position).
+
+assertions:
+  - type: llm_judge
+    criteria: "Category definition is compelling and clear — name, problem statement, buyer persona, landscape, evaluation criteria, and market sizing that could establish a new market"
+    weight: 0.35
+    description: "Compelling category definition"
+  - type: llm_judge
+    criteria: "GTM plan covers all category creation channels — analyst relations, content, community, customer advocacy, PR, and competitive positioning for comprehensive market creation"
+    weight: 0.35
+    description: "Comprehensive category creation GTM"
+  - type: llm_judge
+    criteria: "Economics thesis justifies investment — market creation, category leader economics, valuation impact, and competitive moat arguments that would convince investors"
+    weight: 0.30
+    description: "Investor-convincing economics thesis"

package/courses/upsell-cross-sell-recommendations/scenarios/level-5/expansion-consulting-engagement.yaml

@@ -0,0 +1,86 @@
+meta:
+  id: expansion-consulting-engagement
+  level: 5
+  course: upsell-cross-sell-recommendations
+  type: output
+  description: "Lead a full expansion consulting engagement — assess, design, and implement a complete customer expansion transformation for a client organization"
+  tags: [sales, upsell, cross-sell, consulting, transformation, assessment, master]
+
+state: {}
+
+trigger: |
+  You're a Managing Partner at a revenue growth consulting firm.
+  "UnderExpand Corp" ($500M ARR, 6,000 customers, B2B SaaS) has hired
+  your firm for a $2M engagement to transform their expansion
+  capabilities. Their NRR has been flat at 103% for 3 years while
+  competitors average 118%.
+
+  Discovery findings:
+  Quantitative:
+  - NRR: 103% (3-year flat trend; peer median: 118%)
+  - Gross churn: 11% (peer median: 8%)
+  - Expansion rate: 14% (peer median: 26%)
+  - Expansion as % of new ARR: 18% (peer median: 40%)
+  - Expansion pipeline coverage: 1.5x (should be 3x)
+  - Expansion close rate: 22% (peer median: 35%)
+  - Average expansion deal size: $18K (peer median: $28K)
+  - CSM-to-account ratio: 1:60 (peer median: 1:40)
+  - AMs dedicated to expansion: 12 (should be 30+)
+
+  Qualitative:
+  - No expansion playbook, no standardized process
+  - Product has 3 tiers but no usage-based component or add-ons
+  - CS team measured only on retention, not expansion
+  - No customer marketing for expansion
+  - No deal desk for expansion deals
+  - Product team doesn't consider expansion in roadmap
+  - No AI or analytics for expansion signal detection
+  - Partner channel does zero expansion (referral only)
+  - Executive sponsorship program: doesn't exist
+  - QBRs are check-in meetings, not expansion engines
+
+  Executive sponsor: CEO (focused on IPO in 24 months — NRR is the
+  #1 metric investors will evaluate).
+
+  Tasks:
+  1. Write the "Assessment Report" — the formal deliverable presenting
+     findings to UnderExpand's executive team. Include: the executive
+     summary (3 key findings, financial impact, urgency), the detailed
+     findings by 8 capability areas (strategy, people, process,
+     technology, product, marketing, analytics, partners), the peer
+     benchmark comparison, the root cause analysis (why NRR has been
+     flat despite revenue growth), and the opportunity quantification
+     ($500M ARR × 15% NRR improvement = $75M in additional retained
+     and expanded revenue).
+
+  2. Write the "Transformation Roadmap" — the 18-month plan. Phase 1
+     (Month 1-4): Foundation — expansion playbook, CS restructuring,
+     comp redesign, pipeline process. Phase 2 (Month 5-9): Acceleration
+     — product changes, customer marketing launch, analytics system,
+     deal desk. Phase 3 (Month 10-14): Optimization — AI system, partner
+     expansion, global scaling, executive sponsorship. Phase 4 (Month
+     15-18): Excellence — predictive expansion, customer marketing
+     maturity, IPO readiness. For each phase: deliverables, investment,
+     expected NRR impact, and risks.
+
+  3. Write the "Business Case" — the financial justification. Include:
+     the investment breakdown ($2M consulting + $5M internal), the
+     return by initiative (each initiative's contribution to NRR
+     improvement), the cumulative financial impact (3-year model), the
+     risk-adjusted ROI (conservative/moderate/optimistic), and the
+     IPO valuation impact (NRR improvement → revenue multiple →
+     valuation increase).
+
+assertions:
+  - type: llm_judge
+    criteria: "Assessment is consulting-quality — executive summary, 8 capability areas, benchmarks, root causes, and $75M opportunity quantification for executive audience"
+    weight: 0.35
+    description: "Consulting-quality assessment"
+  - type: llm_judge
+    criteria: "Roadmap is phased and realistic — 4 phases with deliverables, investment, NRR impact, and risks across 18 months of transformation"
+    weight: 0.35
+    description: "Phased realistic roadmap"
+  - type: llm_judge
+    criteria: "Business case justifies investment — breakdown, returns by initiative, 3-year model, risk-adjusted ROI, and IPO valuation impact"
+    weight: 0.30
+    description: "Investment-justifying business case"

package/courses/upsell-cross-sell-recommendations/scenarios/level-5/expansion-industry-benchmark.yaml

@@ -0,0 +1,85 @@
+meta:
+  id: expansion-industry-benchmark
+  level: 5
+  course: upsell-cross-sell-recommendations
+  type: output
+  description: "Build the industry benchmark for expansion — create the definitive benchmarking study that SaaS companies use to evaluate their expansion performance"
+  tags: [sales, upsell, cross-sell, benchmarking, industry-study, research, master]
+
+state: {}
+
+trigger: |
+  You're a research director at a SaaS industry research firm. You've
+  been tasked with creating the definitive "State of SaaS Customer
+  Expansion" benchmark report based on data from 500 SaaS companies.
+  This report will be the industry standard reference.
+
+  Dataset:
+  - 500 B2B SaaS companies surveyed
+  - Revenue range: $5M to $2B ARR
+  - Industries: Technology (35%), Financial Services (15%), Healthcare
+    (12%), Manufacturing (10%), Retail (8%), Other (20%)
+  - Geographic coverage: NA (55%), EMEA (25%), APAC (15%), LATAM (5%)
+
+  Key findings from the data:
+  - Median NRR: 101% (mean: 108%; top quartile: 125%+)
+  - Expansion as % of new ARR: Median 28%, top quartile 48%
+  - Expansion close rate: Median 30%, top quartile 42%
+  - Companies with dedicated expansion teams: 35%
+  - Companies with AI-powered expansion: 12%
+  - Companies with customer marketing for expansion: 22%
+  - Companies with partner expansion programs: 18%
+  - Companies with usage-based pricing: 28%
+  - Average expansion deal size: $28K (enterprise $85K, mid $22K, SMB $8K)
+  - CSM-to-account ratio (expansion-focused): 1:45 median
+
+  Correlation analysis:
+  - Dedicated expansion team → +8% higher NRR
+  - AI-powered expansion → +12% higher NRR
+  - Usage-based pricing → +6% higher NRR
+  - Customer marketing → +5% higher NRR
+  - Executive sponsor program → +7% higher NRR
+  - Partner expansion → +4% higher NRR
+  - Behavioral science in expansion → +9% higher NRR
+  - Product-led expansion → +11% higher NRR
+
+  Tasks:
+  1. Write the "State of SaaS Expansion Report" — the comprehensive
+     benchmark report. Include: the executive summary (top 10 findings),
+     the NRR analysis (distribution, trends, drivers), the expansion
+     capability analysis (what companies are doing and how it
+     correlates with performance), the organizational analysis (team
+     structures, headcount ratios, reporting lines), the technology
+     analysis (tools, AI adoption, automation), and the financial
+     analysis (unit economics, ROI of expansion investment).
+
+  2. Write the "Peer Comparison Framework" — the tool companies use
+     to benchmark themselves. Include: the benchmarking questionnaire
+     (30 questions across 8 categories), the scoring methodology (how
+     to calculate a company's expansion maturity score from answers),
+     the peer group matching (how to identify the right comparison
+     group — by size, industry, model), and the gap analysis template
+     (how to identify where a company over/underperforms vs peers).
+
+  3. Write the "Industry Recommendations" — the strategic guidance
+     based on the data. Include: the top 5 investments for NRR
+     improvement (ranked by impact and cost), the common mistakes
+     (what the bottom quartile does differently), the emerging
+     practices (what early adopters are doing that will become
+     standard), the industry-specific insights (how expansion differs
+     by vertical), and the predictions (where expansion practices
+     are headed in the next 3 years).
+
+assertions:
+  - type: llm_judge
+    criteria: "Benchmark report is authoritative — executive summary, NRR analysis, capability analysis, organizational analysis, technology analysis, and financial analysis from 500-company dataset"
+    weight: 0.35
+    description: "Authoritative benchmark report"
+  - type: llm_judge
+    criteria: "Peer comparison framework is usable — 30-question assessment, scoring methodology, peer matching, and gap analysis that companies could actually use to benchmark themselves"
+    weight: 0.35
+    description: "Usable peer comparison framework"
+  - type: llm_judge
+    criteria: "Recommendations are data-grounded — top 5 investments, common mistakes, emerging practices, and predictions backed by the 500-company dataset correlations"
+    weight: 0.30
+    description: "Data-grounded recommendations"

package/courses/upsell-cross-sell-recommendations/scenarios/level-5/expansion-maturity-model.yaml

@@ -0,0 +1,74 @@
+meta:
+  id: expansion-maturity-model
+  level: 5
+  course: upsell-cross-sell-recommendations
+  type: output
+  description: "Build an expansion maturity model — create the universal assessment framework for evaluating and improving expansion capabilities across SaaS organizations"
+  tags: [sales, upsell, cross-sell, maturity-model, assessment, framework, master]
+
+state: {}
+
+trigger: |
+  You're a thought leader in SaaS expansion strategy. A major SaaS
+  industry association has commissioned you to build the definitive
+  "Expansion Maturity Model" that any SaaS company can use to assess
+  and improve their expansion capabilities. This will become the
+  industry standard.
+
+  Three client organizations of different maturity will test the model:
+
+  Client 1 — "SeedStage" ($5M ARR, Series A, 30 employees):
+  Expansion today: CEO handles all expansion personally. No process,
+  no tools, no dedicated roles. Expansion is opportunistic — when a
+  customer asks for more, they get it. NRR: 95% (net contraction).
+
+  Client 2 — "GrowthStage" ($80M ARR, 300 employees):
+  Expansion today: CS team identifies opportunities, hands to sales.
+  Basic health scoring exists. Some expansion training. No CLM, no
+  analytics, no customer marketing. NRR: 108%.
+
+  Client 3 — "ScaleStage" ($400M ARR, 1,200 employees):
+  Expansion today: Dedicated expansion team, deal desk, CLM, quarterly
+  business reviews, customer marketing program, partner expansion.
+  AI system in pilot. But NRR has plateaued at 118% despite significant
+  investment. Something is preventing the leap to 125%+.
+
+  Tasks:
+  1. Write the "Expansion Maturity Model" — the universal framework
+     with 5 maturity levels and 10 capability dimensions. Levels:
+     Level 1 (Ad-hoc), Level 2 (Emerging), Level 3 (Defined), Level 4
+     (Managed), Level 5 (Optimized). Dimensions: Strategy, Organization,
+     Process, Technology, Analytics, Product, Marketing, Partners,
+     Culture, Customer Experience. For each of the 50 cells (5×10):
+     specific characteristics, behaviors, and outcomes.
+
+  2. Write the "Assessment Reports" for all 3 clients. For each: the
+     maturity score by dimension, the overall maturity level, the
+     key strengths and gaps, the priority recommendations (top 3
+     actions to advance), and the investment estimate. Specifically
+     diagnose why ScaleStage has plateaued at Level 4 despite heavy
+     investment (likely a culture, customer experience, or strategy
+     dimension holding them back).
+
+  3. Write the "Advancement Guide" — how organizations advance from
+     each level to the next. Include: Level 1→2 (survival moves —
+     first expansion process, basic health scoring), Level 2→3
+     (foundation — playbooks, team structure, comp alignment), Level
+     3→4 (management — analytics, AI, customer marketing, partners),
+     Level 4→5 (optimization — behavioral science, predictive models,
+     category leadership). For each: prerequisites, key actions,
+     investment, timeline, and common mistakes that stall advancement.
+
+assertions:
+  - type: llm_judge
+    criteria: "Maturity model is comprehensive — 5 levels across 10 dimensions with specific characteristics for each cell that could assess any SaaS company's expansion capabilities"
+    weight: 0.35
+    description: "Comprehensive 5×10 maturity model"
+  - type: llm_judge
+    criteria: "Three assessments diagnose different stages — SeedStage foundations, GrowthStage scaling, and ScaleStage plateau each accurately assessed with root-cause diagnosis"
+    weight: 0.35
+    description: "Stage-appropriate assessments"
+  - type: llm_judge
+    criteria: "Advancement guide provides clear transitions — level-by-level actions, prerequisites, investment, and common mistakes for organizations at every maturity stage"
+    weight: 0.30
+    description: "Clear advancement transitions"