Should Tradeshift prioritize adding new features to attract enterprise clients or focus on improving the user experience for existing SMB customers?

Introduction

The trade-off we're examining today is whether Tradeshift should prioritize adding new features to attract enterprise clients or focus on improving the user experience for existing SMB customers. This scenario highlights the classic tension between growth and retention in product strategy. 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 Tradeshift's current revenue mix might influence this decision. Could you share the breakdown of revenue between enterprise and SMB clients?

Why it matters: Helps understand the financial impact of focusing on either segment. Expected answer: 60% enterprise, 40% SMB Impact on approach: A higher enterprise revenue share might justify prioritizing new features.

• User Impact: Based on user feedback, I'm assuming SMB customers have specific pain points. What are the top 3 issues reported by SMB users?

Why it matters: Identifies the most critical areas for improving SMB user experience. Expected answer: Onboarding complexity, invoice processing time, integration limitations Impact on approach: Would help prioritize UX improvements for maximum impact.

• Technical Feasibility: Considering the platform architecture, I'm thinking about potential technical debt. How modular is the current system for adding new enterprise features?

Why it matters: Assesses the ease and cost of implementing new features. Expected answer: Moderately modular, some refactoring needed Impact on approach: Might influence timeline and resource allocation for new feature development.

• Resource Allocation: Given the dual focus, I'm curious about team structure. How are product and engineering teams currently organized - by customer segment or feature area?

Why it matters: Determines the flexibility to shift resources between initiatives. Expected answer: Primarily by feature area with some segment specialization Impact on approach: Could impact the feasibility of pursuing both strategies simultaneously.

• Timeline Pressure: Considering market dynamics, I'm wondering about competitive pressure. Are there any upcoming competitor launches or market events that might influence our timeline?

Why it matters: Helps prioritize short-term vs. long-term strategies. Expected answer: Major competitor expanding enterprise offerings in Q4 Impact on approach: Might necessitate faster development of enterprise features.