Should Oyster prioritize expanding its global employment platform to more countries or focus on deepening features for existing supported locations?

Introduction

The trade-off we're examining today is whether Oyster should prioritize expanding its global employment platform to more countries or focus on deepening features for existing supported locations. This decision is crucial for Oyster's growth strategy and market positioning. I'll analyze this trade-off by considering the business context, user impact, technical feasibility, and resource allocation.

Step 1

Clarifying Questions (3 minutes)

• Business Context: I'm thinking Oyster's current revenue model might heavily influence this decision. Could you share how our revenue is currently distributed between existing markets and new market entries?

Why it matters: Helps understand the financial implications of expansion vs. deepening Expected answer: Majority revenue from existing markets, but new markets show high growth potential Impact on approach: Would lean towards a balanced strategy if both contribute significantly

• User Impact: Based on user feedback, I'm assuming there might be feature gaps in existing markets. Can you confirm if we've received any consistent feature requests from current customers?

Why it matters: Identifies immediate user needs and potential for increased satisfaction Expected answer: Yes, several key features requested across multiple existing markets Impact on approach: Would prioritize deepening features if user demands are strong

• Technical Feasibility: Considering our current architecture, I'm thinking expanding to new countries might require significant backend changes. How scalable is our current system for adding new countries?

Why it matters: Determines the technical effort required for expansion Expected answer: Moderately scalable, but some customization needed for each new country Impact on approach: Would influence timeline and resource allocation for expansion

• Resource Allocation: Given our team structure, I'm curious about our capacity for parallel development. Do we have separate teams for new market expansion and feature development, or is it a shared resource pool?

Why it matters: Affects our ability to pursue both strategies simultaneously Expected answer: Shared resource pool with some specialization Impact on approach: Would impact the feasibility of a dual-focus strategy

• Timeline Pressure: Considering market dynamics, I'm wondering if there's any urgency to enter specific new markets. Are there any time-sensitive opportunities or competitive pressures we should be aware of?

Why it matters: Helps prioritize expansion if there are immediate market opportunities Expected answer: A few key markets showing rapid growth in remote work adoption Impact on approach: Would influence the balance between expansion and deepening based on market timing