Developing a Year Long Product Roadmap

Overview

This case study covers the development of a comprehensive year-long product roadmap for Dexible that balanced immediate market needs with long-term strategic goals.

Challenge

Dexible faced competing priorities:

• Rapid market changes requiring frequent pivots
• Multiple stakeholder groups with different needs (users, partners, investors)
• Limited engineering resources requiring careful prioritization
• Technical debt requiring attention alongside new features

Solution

I developed a collaborative roadmapping process that included:

• **Stakeholder Alignment**: Quarterly planning sessions with executives, engineering, and key partners
• **Customer Research**: Direct feedback from top users and partners
• **Market Analysis**: Competitive and market trend assessment
• **Phased Planning**: Quarterly execution plans with annual strategic themes

The roadmap was structured in three tiers:

1. **Quarterly Commitments**: High-confidence deliverables aligned with team capacity
2. **Annual Initiatives**: Strategic bets with flexible timelines
3. **On-Demand**: Rapid response features for market opportunities

Results

The structured roadmapping approach achieved:

• **Increased organizational clarity** on priorities and direction
• **Improved stakeholder confidence** through transparency
• **Better execution** with 85% on-time delivery
• **Market responsiveness** with quarterly flexibility
• **Aligned team** across product, engineering, and business functions