What Went Wrong...
Examining the missteps of various software products across industries reveals common pitfalls that can derail even the most promising innovations. From inadequate market research and poor user experience design to insufficient testing and failure to adapt to technological advancements, these challenges underscore the importance of thorough planning and execution. The following section outlines specific cases, offering insights into how these factors contributed to their downfall and the lessons that can be gleaned to inform future endeavors.
Available Lessons:
200
FTX Trading Platform
FinTech
FTX
The cryptocurrency exchange collapsed due to software issues masking financial mismanagement, fraudulent activities, and lack of transparency.
WHAT WENT WRONG
Nonexistent risk management controls in trading algorithms
Poor transparency for financial reporting tools
SIGNALS MISSED
Early reports of missing customer funds
Internal concerns ignored over algorithm behavior
HOW COULD THEY HAVE AVOIDED THIS
Establishing robust financial reporting and audit tools
Building transparent, compliant software infrastructure
TEAMS INVOLVED
Product, Engineering, CEO, Compliance, Risk Management
Better Digital Mortgage Platform
FinTech
Better.com
Software bugs in Better’s automated loan approval system led to inaccuracies in mortgage offers, frustrating customers.
WHAT WENT WRONG
Automation errors in approval algorithms
Insufficient manual checks to validate results
SIGNALS MISSED
Internal testing reports showing approval mismatches
Rising volume of customer complaints
HOW COULD THEY HAVE AVOIDED THIS
Combining AI-driven automation with manual oversight
Expanding QA processes for edge cases
TEAMS INVOLVED
Product, Engineering, Risk Management, Customer Success
Square Payroll (Initial Launch)
FinTech
Square (now Block)
Square Payroll failed to integrate smoothly with third-party accounting software, leading to errors in payroll calculations and compliance issues.
WHAT WENT WRONG
Limited testing for external integrations
Inadequate support for payroll tax updates
SIGNALS MISSED
High volume of support tickets reporting tax miscalculations
Early warnings from beta testers on integration bugs
HOW COULD THEY HAVE AVOIDED THIS
Prioritizing robust third-party integrations pre-launch
Continuous compliance checks for evolving payroll tax rules
TEAMS INVOLVED
Product, Engineering, Compliance, Customer Success
TransferWise Borderless Account
FinTech
TransferWise (now Wise)
Early iterations of the multi-currency account struggled with bugs in fund transfers and lacked a seamless mobile experience.
WHAT WENT WRONG
Poor performance of international transaction APIs
Mobile app issues for real-time account management
SIGNALS MISSED
Delays in cross-border transaction processing
Negative user feedback regarding app usability
HOW COULD THEY HAVE AVOIDED THIS
Focusing on mobile optimization and stable APIs pre-launch
Stress-testing international transfer systems
TEAMS INVOLVED
Product, Engineering, Operations, Design
Quibi Financial Subscription Platform
FinTech
Quibi
Quibi failed in its attempt to link short-form content with subscription-based micropayments, leading to poor user adoption.
WHAT WENT WRONG
Over-reliance on untested micropayment processing tools
Poor integration with user payment gateways
SIGNALS MISSED
High payment processing failure rates
Low conversion during user onboarding
HOW COULD THEY HAVE AVOIDED THIS
Validating payment models with user cohorts before launch
Simplifying payment flows for seamless user experience
TEAMS INVOLVED
Product, Engineering, Marketing, Design
Mint Premium
FinTech
Intuit
Mint’s attempt to introduce premium features failed to provide enough value for users already accustomed to its free financial tracking tools.
WHAT WENT WRONG
Poor differentiation of premium features from the free version
Misalignment with user willingness to pay
SIGNALS MISSED
Low premium feature activation during trials
Negative feedback about redundant features
HOW COULD THEY HAVE AVOIDED THIS
Conducting user research to identify high-value premium features
Introducing a gradual freemium model with clear value add
TEAMS INVOLVED
Product, Marketing, Design, Customer Success