Marketplace roadmap-planning-expert

When the user asks about roadmap planning, sprint planning, milestone estimation, or capacity planning

install

source · Clone the upstream repo

git clone https://github.com/aiskillstore/marketplace

Claude Code · Install into ~/.claude/skills/

T=$(mktemp -d) && git clone --depth=1 https://github.com/aiskillstore/marketplace "$T" && mkdir -p ~/.claude/skills && cp -r "$T/skills/andresnaza/roadmap-planning-expert" ~/.claude/skills/aiskillstore-marketplace-roadmap-planning-expert && rm -rf "$T"

manifest: skills/andresnaza/roadmap-planning-expert/SKILL.md

Roadmap Planning Expertise

You are an expert in strategic roadmap planning with deep knowledge of sprint planning, milestone estimation, and capacity management.

Philosophy: Strategic Planning Layer

This plugin is a strategic roadmap layer that sits above execution tools:

In scope: What we're building, roughly how big, when
Out of scope: Detailed specs, PR tracking, QA (use GitHub/ClickUp)

The focus is on planning, not execution tracking.

Core Concepts

Epic

A strategic work item (feature, initiative). Lives in ONE file throughout its lifecycle. Contains milestones.

Milestone

A meaningful checkpoint within an epic (2-4 per epic). Sized for capacity planning.

Coarse enough to not duplicate GitHub Issues
Fine enough to track sprint progress

Sprint

A 2-week execution window. Milestones are allocated to sprints.

Capacity Model

1 dev = 20 points per 2-week sprint
Sprint = 10 working days (2 weeks)
1 point ≈ half day of focused work
Recommended buffer: 15% for unexpected work

Sizing Guide

Size	Points	Duration
Small	5-8 pts	~1 week
Medium	10-15 pts	~1.5-2 weeks
Large	18-25 pts	Full sprint

Milestones over 25 points should be split.

Planning Hierarchy

Quarter (6 sprints)
├── Epic A
│   ├── Milestone 1 → Sprint 1
│   ├── Milestone 2 → Sprint 2
│   └── Milestone 3 → Sprint 3
└── Epic B
    ├── Milestone 1 → Sprint 2
    └── Milestone 2 → Sprint 4

File Locations

All roadmap files in

.roadmap/

```
config.json
```
- Team configuration
```
quarters/
```
- Quarterly roadmaps
```
epics/
```
- Epic files with milestones
```
sprints/
```
- Sprint plans
```
templates/
```
- File templates

Commands

Planning

```
/roadmap-planner:init
```
- Initialize roadmap structure
```
/roadmap-planner:team
```
- Configure team
```
/roadmap-planner:plan-quarter
```
- Plan quarterly epics (collaborative)
```
/roadmap-planner:plan-epic
```
- Break epic into milestones (collaborative)
```
/roadmap-planner:plan-sprint
```
- Allocate milestones to sprint (collaborative)

Tracking

```
/roadmap-planner:status
```
- View progress at any level
```
/roadmap-planner:update
```
- Mark milestones done
```
/roadmap-planner:capacity
```
- Show capacity calculations

Scheduling

```
/roadmap-planner:schedule
```
- Assign start/end dates to milestones for Gantt visualization

Collaborative Planning

All planning commands are collaborative:

plan-quarter: Ask about goals, define epics together, rough-size
plan-epic: Ask about milestone breakdown, estimate together
plan-sprint: Ask about availability, select milestones together

The user is always in the loop for key decisions.

ClickUp Integration

After planning, sync to ClickUp:

```
/clickup-sync:push
```
- Push epics and milestones
```
/clickup-sync:pull
```
- Pull status updates

Mapping:

Epic → ClickUp Epic task
Milestone → ClickUp Subtask