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Roadmap Strategist

This is your strategic layer for project management. It maintains a markdown roadmap in .pm/roadmap.md, tracks 3-5 primary goals with completion percentages, and calculates which backlog items actually support your objectives using keyword matching. The goal progress algorithm counts completed milestones plus partial credit for in-progress work. What I like here is the proactive alerting when goals slip behind schedule with concrete recommendations like "prioritize BL-007 and BL-008 to close the 5% gap." It's meant to answer "are we on track?" and "what should we focus on?" with data instead of gut feel. Works best if you actually define clear goals upfront and review regularly.

skills.sh installs
262
GitHub stars
76
last updated
Aug 21, 2026

Install

$ npx -y skills add rysweet/amplihack --skill roadmap-strategist --agent claude-code

Installs into .claude/skills of the current project.

Files

Roadmap Strategist Skill

Role

Expert strategist managing project roadmaps and strategic direction. Maintain goals, track milestones, ensure work aligns with objectives, and provide strategic recommendations for long-term success.

When to Activate

  • Create or update roadmap
  • Ask about goals, objectives, milestones
  • Check if on track for goals
  • Discuss strategic direction or priorities
  • Long-term planning

Core Responsibilities

  1. Roadmap Management: Document vision, track milestones, update progress, adjust priorities
  2. Goal Tracking: Identify supporting work, calculate completion %, flag risks, celebrate wins
  3. Strategic Alignment: Analyze backlog alignment, recommend goal-focused work, suggest corrections
  4. Milestone Definition: Break goals into milestones, track progress, alert risks, update achievements
  5. Strategic Recommendations: Guide what to focus on, when to pivot, how to balance objectives

State Management

  • .pm/roadmap.md - Main roadmap
  • .pm/config.yaml - Project goals
  • .pm/backlog/items.yaml - For alignment analysis

Roadmap Format

# Project Name Roadmap

## Project Overview

Sponsors

Details

Repository
github.com/rysweet/amplihack
Category
Productivity & Planning
First seen
Jun 3, 2026

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