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+---
+name: portfolio-roadmapping-bets
+description: Use when managing multiple initiatives across time horizons (now/next/later, H1/H2/H3), balancing risk vs return across portfolio, sizing and sequencing bets with dependencies, setting exit/scale criteria for experiments, allocating resources across innovation types (core/adjacent/transformational), or when user mentions portfolio planning, roadmap horizons, betting framework, initiative prioritization, innovation portfolio, or resource allocation across horizons.
+---
+# Portfolio Roadmapping Bets
+
+## Table of Contents
+1. [Purpose](#purpose)
+2. [When to Use](#when-to-use)
+3. [What Is It?](#what-is-it)
+4. [Workflow](#workflow)
+5. [Common Patterns](#common-patterns)
+6. [Guardrails](#guardrails)
+7. [Quick Reference](#quick-reference)
+
+## Purpose
+
+Create strategic portfolio roadmaps that balance exploration vs exploitation, size bets by effort and impact, sequence initiatives across time horizons, and set clear exit/scale criteria for disciplined resource allocation.
+
+## When to Use
+
+**Use this skill when:**
+
+### Portfolio Context
+- Managing 5+ initiatives requiring sequencing and trade-offs
+- Balancing quick wins vs strategic bets vs R&D exploration
+- Allocating scarce resources (budget, people, time) across competing priorities
+- Planning across multiple time horizons (H1: 0-6mo, H2: 6-12mo, H3: 12-24mo+)
+
+### Decision Complexity
+- Initiatives have dependencies requiring careful sequencing
+- Exit criteria needed to kill or scale experiments
+- Risk/return profiles vary widely (low-risk incremental vs high-risk transformational)
+- Portfolio balance matters (70% core, 20% adjacent, 10% transformational)
+
+### Stakeholder Communication
+- Executives need portfolio-level view of roadmap with strategic rationale
+- Teams need clarity on what's now vs next vs later
+- Investors or board want visibility into innovation pipeline and resource allocation
+
+**Do NOT use when:**
+- Single initiative with clear priority (use one-pager-prd or project-risk-register instead)
+- Purely operational prioritization without strategic horizons (use prioritization-effort-impact)
+- No resource constraints or trade-offs (just do everything)
+
+## What Is It?
+
+**Portfolio Roadmapping Bets** is a framework for managing a portfolio of initiatives across time horizons using betting language to:
+- **Size bets**: Estimate effort (S/M/L) and impact (1x/3x/10x potential)
+- **Sequence bets**: Order initiatives based on dependencies, learning, and strategic timing
+- **Set bet criteria**: Define what success looks like (scale) and when to exit (kill)
+- **Balance portfolio**: Ensure healthy mix across risk profiles and horizons
+- **Review bets**: Periodic check-ins to kill losers, double-down on winners
+
+**Quick Example:**
+
+**Theme:** Grow marketplace revenue 3x in 18 months
+
+**H1 Bets (Now, 0-6 months):**
+- **Bet 1**: Improve search relevance (Medium effort, 1.5x GMV) - Scale if CTR +20%
+- **Bet 2**: Add "Buy It Now" pricing (Small, 1.3x GMV) - Exit if <5% adoption in 60 days
+
+**H2 Bets (Next, 6-12 months):**
+- **Bet 3**: Launch seller analytics dashboard (Large, 1.8x GMV) - Depends on Bet 1 data pipeline
+- **Bet 4**: Experiment with auction format (Medium, 3x potential) - Exit if fraud risk >2%
+
+**H3 Bets (Later, 12-24 months):**
+- **Bet 5**: Build AI recommendation engine (X-Large, 10x potential) - Depends on Bets 1+3 data
+
+**Portfolio Balance**: 60% core (Bets 1-2), 30% adjacent (Bets 3-4), 10% transformational (Bet 5)
+
+## Workflow
+
+Copy this checklist and track your progress:
+
+```
+Portfolio Roadmapping Bets Progress:
+- [ ] Step 1: Define portfolio theme and constraints
+- [ ] Step 2: Inventory and size all bets
+- [ ] Step 3: Sequence bets across horizons
+- [ ] Step 4: Set exit and scale criteria
+- [ ] Step 5: Balance and validate portfolio
+```
+
+**Step 1: Define portfolio theme and constraints**
+
+Clarify the strategic theme (north star), time horizons (H1/H2/H3 definitions), resource constraints (budget, people, time), and portfolio balance targets (e.g., 70/20/10 rule). See [Portfolio Theme & Constraints](#portfolio-theme--constraints) for guidance.
+
+**Step 2: Inventory and size all bets**
+
+List all candidate initiatives, size each by effort (S/M/L/XL) and impact potential (1x/3x/10x), categorize by type (core/adjacent/transformational), and identify dependencies. For simple cases use [resources/template.md](resources/template.md). For complex cases with 15+ bets or multiple themes, study [resources/methodology.md](resources/methodology.md).
+
+**Step 3: Sequence bets across horizons**
+
+Assign each bet to H1 (now), H2 (next), or H3 (later) based on dependencies, strategic timing, learning sequencing, and capacity constraints. See [Sequencing & Dependencies](#sequencing--dependencies) for sequencing heuristics.
+
+**Step 4: Set exit and scale criteria**
+
+For each bet, define what success looks like (scale criteria: double down, expand scope) and what failure looks like (exit criteria: kill, deprioritize, pivot). See [Exit & Scale Criteria](#exit--scale-criteria) for examples.
+
+**Step 5: Balance and validate portfolio**
+
+Check portfolio balance (are we too conservative or too aggressive?), validate resource feasibility (can we actually staff this?), and self-assess using [resources/evaluators/rubric_portfolio_roadmapping_bets.json](resources/evaluators/rubric_portfolio_roadmapping_bets.json). Minimum standard: ≥3.5 average score. See [Portfolio Balance Checks](#portfolio-balance-checks).
+
+## Common Patterns
+
+### By Portfolio Type
+
+**Product Portfolio** (multiple features/products):
+- H1: Ship quick wins and critical bugs
+- H2: Strategic features with cross-product dependencies
+- H3: Platform bets and R&D exploration
+- Balance: 60% incremental, 30% substantial, 10% breakthrough
+
+**Technology Portfolio** (platform, infrastructure, tech debt):
+- H1: Stability, security, performance quick wins
+- H2: Major migrations and platform upgrades
+- H3: Next-gen architecture and tooling
+- Balance: 50% maintain, 30% improve, 20% transform
+
+**Innovation Portfolio** (R&D, experiments, ventures):
+- H1: Validated experiments ready to scale
+- H2: Active experiments with checkpoints
+- H3: Early-stage exploration and research
+- Balance: 70% core business, 20% adjacent, 10% transformational (McKinsey Horizons)
+
+**Marketing Portfolio** (campaigns, channels, experiments):
+- H1: Proven channels with optimization
+- H2: New channel experiments and tests
+- H3: Brand building and long-term positioning
+- Balance: 70% performance marketing, 20% growth experiments, 10% brand
+
+### By Bet Size
+
+**Small Bets** (1-2 weeks, 1-2 people):
+- Low effort, low-to-medium impact
+- Use for quick wins, experiments, bug fixes
+- Example: A/B test new pricing page (2 weeks, 1.2x conversion potential)
+
+**Medium Bets** (1-3 months, 3-5 people):
+- Moderate effort, moderate-to-high impact
+- Use for features, improvements, small initiatives
+- Example: Build seller dashboard (2 months, 1.8x seller retention)
+
+**Large Bets** (3-6 months, 5-10 people):
+- High effort, high impact
+- Use for strategic initiatives, platform work, major features
+- Example: Marketplace trust & safety system (5 months, 3x GMV via reduced fraud)
+
+**X-Large Bets** (6-12+ months, 10+ people):
+- Very high effort, transformational impact potential
+- Use for platform rewrites, new business lines, moonshots
+- Example: AI-powered recommendation engine (9 months, 10x engagement potential)
+
+### By Risk Profile
+
+**Core Bets** (Low Risk, Incremental Return):
+- Optimize existing products/channels
+- Proven approaches with clear ROI
+- Example: Improve search relevance from 65% → 75% accuracy
+
+**Adjacent Bets** (Medium Risk, Substantial Return):
+- Extend to new use cases, segments, or capabilities
+- Validated approach, new application
+- Example: Launch seller analytics (proven feature, new user segment)
+
+**Transformational Bets** (High Risk, Breakthrough Return):
+- New business models, technologies, or markets
+- Unproven approach, high uncertainty
+- Example: Blockchain-based ownership system (unproven tech, could unlock new market)
+
+## Portfolio Theme & Constraints
+
+Define the strategic anchor for your portfolio:
+
+**Theme**: The overarching goal (e.g., "Grow enterprise revenue 3x", "Achieve platform parity", "Launch in APAC")
+
+**Time Horizons**:
+- **H1 (Now)**: 0-6 months - High confidence, shipping soon
+- **H2 (Next)**: 6-12 months - Medium confidence, in planning/development
+- **H3 (Later)**: 12-24+ months - Lower confidence, exploration/research
+
+**Resource Constraints**:
+- Budget: $X available across all initiatives
+- People: Y engineers, Z designers, etc. (capacity by function)
+- Time: When must key milestones be hit? (launch date, board meeting, fiscal year)
+
+**Portfolio Balance Targets**:
+- Example: 70% core / 20% adjacent / 10% transformational (McKinsey Three Horizons)
+- Example: 60% product features / 30% platform / 10% R&D
+- Example: 50% H1 / 30% H2 / 20% H3 (de-risk near term while investing in future)
+
+## Sequencing & Dependencies
+
+**Types**: Technical (infrastructure), Learning (insights), Strategic (validation), Resource (capacity)
+
+**Heuristics**: Dependencies first, learn before scaling, quick wins early, long bets start early, hedge portfolio
+
+## Exit & Scale Criteria
+
+**Exit** (kill): Time-based ("90 days"), Metric ("<5% adoption"), Cost (">$X"), Strategic ("market shifts")
+**Scale** (double-down): Adoption (">20%"), Engagement (">3x baseline"), Revenue (">1.5x target"), Efficiency ("<$X CAC")
+
+**Example**: AI chatbot bet | Exit: Deflection <30% after 60d OR sentiment <-20% | Scale: Deflection >50% AND sentiment >70%
+
+## Portfolio Balance Checks
+
+**Risk**: ✓ ~70% core, ~20% adjacent, ~10% transformational | ❌ >80% core (too safe) or >30% transformational (too risky)
+**Horizon**: ✓ ~50-60% H1, ~25-30% H2, ~15-20% H3 | ❌ >70% H1 (no future) or >40% H3 (no near-term)
+**Capacity**: Effort ≤ capacity × 0.8 (20% slack) | Example: 10 eng → 48 EM/6mo → max 38 EM in H1
+**Impact**: Portfolio ladders to theme (risk-adjusted) | Example: "3x revenue" → bets sum to 4.7x potential → 50% fail = 2.35x expected → add more bets
+
+## Guardrails
+
+**Problem Framing**:
+- ❌ Vague theme like "improve product" → ✓ Specific like "Reduce churn from 5% to 2% in 12 months"
+- ❌ No constraints (infinite resources) → ✓ Explicit budget, people, time limits
+- ❌ Missing portfolio balance targets → ✓ Define risk tolerance (e.g., 70/20/10)
+
+**Bet Sizing**:
+- ❌ Effort in person-days without context → ✓ Use S/M/L/XL relative sizing
+- ❌ Impact as vague "high/medium/low" → ✓ Use multipliers (1x/3x/10x) or concrete metrics
+- ❌ All bets are "high priority" → ✓ Force-rank or categorize by type
+
+**Sequencing**:
+- ❌ No dependencies identified → ✓ Map technical, learning, strategic dependencies
+- ❌ All bets in H1 (wish list) → ✓ Realistic capacity-constrained sequencing
+- ❌ No rationale for sequence → ✓ Explain why A before B (dependency, learning, quick win)
+
+**Exit & Scale Criteria**:
+- ❌ No criteria (just "we'll see") → ✓ Specific metrics and timelines for kill/scale decisions
+- ❌ Only exit criteria (pessimistic) → ✓ Include scale criteria (what does wild success look like?)
+- ❌ Unmeasurable criteria → ✓ Use quantifiable metrics with baselines
+
+**Portfolio Balance**:
+- ❌ All core (too safe) or all transformational (too risky) → ✓ Balanced risk distribution
+- ❌ Sum of efforts exceeds capacity → ✓ Effort ≤ capacity × 0.8 (20% slack for unknowns)
+- ❌ Expected impact below strategic goal → ✓ Portfolio ladders up to theme with risk adjustment
+
+## Quick Reference
+
+**Resources**:
+- [resources/template.md](resources/template.md) - Portfolio roadmap structure and bet template
+- [resources/methodology.md](resources/methodology.md) - Horizon planning, bet sizing frameworks, portfolio balancing techniques
+- [resources/evaluators/rubric_portfolio_roadmapping_bets.json](resources/evaluators/rubric_portfolio_roadmapping_bets.json) - Quality criteria for portfolio roadmaps
+
+**Success Criteria**:
+- ✓ Strategic theme is clear and measurable
+- ✓ All bets sized by effort (S/M/L/XL) and impact (1x/3x/10x)
+- ✓ Bets sequenced across H1/H2/H3 with dependency rationale
+- ✓ Exit and scale criteria defined for each bet
+- ✓ Portfolio balanced across risk profiles and horizons
+- ✓ Total effort ≤ team capacity (with 20% slack)
+- ✓ Expected portfolio impact ≥ strategic goal (risk-adjusted)
+
+**Common Mistakes**:
+- ❌ No strategic theme → roadmap becomes random wish list
+- ❌ All bets sized "Large" → no useful prioritization
+- ❌ No exit criteria → sunk cost fallacy, zombie projects
+- ❌ Portfolio imbalanced → all quick wins (no future) or all moonshots (no near-term value)
+- ❌ Dependencies ignored → H1 bets blocked by H2 infrastructure
+- ❌ Over-capacity → team burns out, quality suffers
+- ❌ Under-ambitious → portfolio impact below strategic goal even if everything succeeds