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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

Walmart Scan & Go

RetailTech

Walmart

A mobile checkout system failed due to low consumer adoption and challenges with theft prevention.

WHAT WENT WRONG

  • Poor UX and usability in stores

  • Lack of robust security measures to prevent misuse

SIGNALS MISSED

  • Low engagement during pilot tests

  • Feedback about difficulty scanning items in busy environments

HOW COULD THEY HAVE AVOIDED THIS

  • Improving UX through customer testing and feedback loops

  • Adding theft-prevention mechanisms like automated auditing

TEAMS INVOLVED

Product, Engineering, Customer Success, Operations

Amazon Dash Buttons

RetailTech

Amazon

Physical buttons for instant product reordering failed due to limited consumer adoption and the rise of voice assistants like Alexa.

WHAT WENT WRONG

  • Poor scalability as consumer habits shifted toward voice and app-based shopping

  • Limited use cases for multiproduct households

SIGNALS MISSED

  • Low engagement rates compared to app usage

  • Consumer confusion about managing multiple buttons

HOW COULD THEY HAVE AVOIDED THIS

  • Focusing on app-based alternatives or voice integrations

  • Conducting deeper consumer research on shopping behaviors

TEAMS INVOLVED

Product, Marketing, Operations, Design

CoStar Tenant Analysis Tool

PropTech

CoStar Group

A tool designed for commercial real estate tenant insights failed due to inaccurate data and lack of actionable insights.

WHAT WENT WRONG

  • Incomplete and outdated data sources

  • Weak analytics tools for generating insights

SIGNALS MISSED

  • Complaints from brokers about irrelevant or incorrect data

  • Poor renewal rates among enterprise customers

HOW COULD THEY HAVE AVOIDED THIS

  • Partnering with reliable data providers for better accuracy

  • Adding actionable recommendations for tenants and brokers

TEAMS INVOLVED

Product, Data, Engineering, Customer Success

eBay Now

RetailTech

eBay

A same-day delivery service failed due to logistical inefficiencies and high operational costs.

WHAT WENT WRONG

  • Poor scalability of delivery logistics

  • Limited geographic reach and product selection

SIGNALS MISSED

  • High operational costs reported in pilot cities

  • Limited retailer participation in key markets

HOW COULD THEY HAVE AVOIDED THIS

  • Partnering with third-party logistics providers

  • Testing scalability in smaller regions before expanding

TEAMS INVOLVED

Product, Operations, Engineering, Marketing

SmartRent Energy Management

PropTech

SmartRent

A tool for managing energy consumption in rental properties failed due to technical glitches and limited adoption by property managers.

WHAT WENT WRONG

  • Bugs in energy tracking and reporting

  • Poor integration with existing smart home systems

SIGNALS MISSED

  • Feedback about inconsistent energy tracking results

  • Low adoption rates among property managers

HOW COULD THEY HAVE AVOIDED THIS

  • Resolving technical issues before launch

  • Building partnerships with smart home system providers

TEAMS INVOLVED

Product, Engineering, Customer Success, Sales

RentPath AI Recommendations

PropTech

RentPath

AI-driven rental recommendations failed to deliver relevant matches, leading to user frustration and churn.

WHAT WENT WRONG

  • Poor training of AI models for diverse user preferences

  • Weak feedback loops to improve recommendation accuracy

SIGNALS MISSED

  • Complaints about irrelevant rental recommendations

  • Low click-through rates on recommended properties

HOW COULD THEY HAVE AVOIDED THIS

  • Refining AI models with real-world user behavior data

  • Building feedback loops to learn from user interactions

TEAMS INVOLVED

Product, AI, Data, Engineering

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