Roadmap Migration — Case Study

Product Operations · Stakeholder Engagement

Notion to
Jira Product
Discovery

Migrated a fragmented product roadmap from Notion into Jira Product Discovery across a 200-person Engineering, Product, Data, and Design organization — creating a single source of truth for planning, prioritization, and delivery.

Org Size 200-Person EPDD Org

Role Manager, Program Management & Ops

Tools Jira Product Discovery · Notion

Impact 15% faster planning cycles

📄 Product Roadmap — Master

Roadmap

Initiative

Status

Owner

Mobile app launch — market 1

Now

Eng?

Core product feature — v2

TBD

Data platform rebuild

Unclear

—

Design system v3

Later

Design

AI enablement initiative

Unclear

???

💡 Notion worked well early on — but cross-team visibility and prioritization at scale needed a more structured home.

↓

Migrated &
Structured

Now

Mobile app launch · market 1

Eng PRD ✓

Core product feature — v2 — core betting loop

Product Score: 87

Data platform rebuild — phase 1

Data Score: 74

AI enablement — discovery phase

Eng PRD ✓

Later

Design system v3

Design Score: 52

Offshore team expansion

Eng Score: 48

The Problem

The right team. The wrong tool for the scale.

A 200-person Engineering, Product, Data, and Design org was moving fast — and Notion had served them well to get there. But at this scale and pace, a single shared roadmap needed more structure than a doc-based tool could provide. Prioritization, dependency tracking, and cross-team visibility were increasingly difficult to maintain, and the team needed a system that could keep up.

200

Person org across Engineering, Product, Data, and Design impacted by the migration

15%

Faster planning cycles after migration and framework implementation

50%

Improvement in delivery transparency and executive visibility into ROI

Source of truth — replacing fragmented Notion docs across multiple teams

What I Did

Full setup, end to end.

Stakeholder Discovery

Ran structured discovery sessions with engineering and product leads to understand how roadmap decisions were actually being made, where the friction lived, and what each team needed from a shared system.

Jira Product Discovery Setup

Configured Jira Product Discovery from scratch — workspace structure, Now/Next/Later framework, prioritization scoring, field definitions, and permission model across all four disciplines.

Roadmap Migration

Consolidated all existing Notion roadmap content — across multiple team versions — into a single structured Jira backlog. Disambiguated duplicates, resolved conflicting statuses, and assigned ownership where none existed.

PRD Template & Standards

Built a standardized high-level PRD template for new initiatives entering the roadmap — covering problem statement, goals, success metrics, scope, acceptance criteria, and dependencies. Embedded it directly into the Jira workflow.

Prioritization Framework

Introduced a scoring model for roadmap prioritization — giving teams a shared language for Now/Next/Later decisions grounded in impact, effort, and strategic alignment.

Team Enablement & Adoption

Facilitated working sessions with engineering and product leads to walk through the new system, establish norms for how it would be maintained, and build the habits that would keep it running well.

How I Did It

Listen first.
Build second.
Anchor third.

Tool migrations fail when they're treated as IT projects. This one worked because it was treated as a people and alignment project first.

Step 01

Mapped the Current State

Before touching any tooling, I spent time with engineering and product leads understanding how roadmap decisions were actually being made. What was in Notion, what wasn't, what lived in people's heads, and where the real planning was happening. Notion had worked well in the early days — the goal was to find a system that could scale with where the team was going.

Discovery Stakeholder Interviews Process Mapping

Step 02

Designed the Jira Structure

Set up Jira Product Discovery to reflect how the org actually worked — not a generic template. Configured the Now/Next/Later framework, built out the prioritization scoring model, defined field standards, and established the PRD template that every new initiative would require before entering the roadmap.

Jira Product Discovery Systems Design PRD Standards

Step 03

Ran the Migration

Pulled all roadmap content from Notion — across every team's version — into Jira. Reconciled conflicts, removed duplicates, clarified ambiguous statuses, and assigned owners to everything that had been floating without accountability. Every item got a score, a bucket, and a home.

Migration Data Reconciliation Ownership Assignment

Step 04

Facilitated Adoption with the Team

Ran working sessions with engineering and product leads — including a full offsite roadmap session where the team built out the Now/Next/Later view together in real time. Established norms for how the roadmap would be maintained, reviewed, and updated. The goal wasn't just to migrate — it was to make Jira the place where roadmap conversations actually happened.

Facilitation Change Management Offsite Planning

The Outcome

One roadmap. Everyone in it.

A fragmented planning process became a shared operating system — and planning cycles got measurably faster because of it.

✓

15% faster planning cycles — a direct result of consolidating the roadmap into a single structured system with shared prioritization language.

✓

50% improvement in delivery transparency — leadership had real visibility into what was happening across all four disciplines for the first time.

✓

Single source of truth established — one shared, up-to-date view of the roadmap that every team could trust and work from.

✓

Prioritization made objective — the scoring model gave teams a shared framework for Now/Next/Later decisions, reducing planning debate and increasing confidence in sequencing.

✓

PRD standards embedded — every new initiative entering the roadmap required a structured brief, improving the quality and completeness of what engineering and product were asked to build.

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