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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

Oath Ad Platform

AdTech

Verizon Media

Combined Yahoo and AOL’s ad platforms but failed to integrate technologies effectively, leading to inefficiencies and low ROI for advertisers.

WHAT WENT WRONG

  • Poorly executed platform integration

  • Confusion over branding and value proposition

SIGNALS MISSED

  • Feedback from advertisers about platform inefficiencies

  • Declining ad spend compared to competitors

HOW COULD THEY HAVE AVOIDED THIS

  • Streamlining technology stacks before public rollout

  • Clear branding and value communication to advertisers

TEAMS INVOLVED

Product, Engineering, Sales, Marketing

Microsoft Advertising Analytics (2015 Version)

AdTech

Microsoft

Promised enhanced campaign analytics but failed due to outdated UI and limited actionable insights for advertisers.

WHAT WENT WRONG

  • Weak analytics tools compared to Google Ads

  • Poor user experience with data visualization

SIGNALS MISSED

  • Feedback highlighting lack of competitive features

  • Low retention rates among advertising clients

HOW COULD THEY HAVE AVOIDED THIS

  • Developing analytics tools with actionable insights

  • Improving the design and usability of reporting dashboards

TEAMS INVOLVED

Product, Design, Data, Engineering

Constant Contact Social Campaigns

MarTech, AdTech

Constant Contact

The feature for running social media campaigns failed to compete with tools like Buffer and Hootsuite due to limited functionality.

WHAT WENT WRONG

  • Weak scheduling and analytics capabilities

  • Lack of differentiation from competitors

SIGNALS MISSED

  • Low user engagement compared to competitors

  • Feedback highlighting missing features like advanced scheduling

HOW COULD THEY HAVE AVOIDED THIS

  • Conducting competitive analysis before launch

  • Adding unique features to stand out in the market

TEAMS INVOLVED

Product, Marketing, Design, Engineering

Sizmek Ad Management Platform

AdTech

Sizmek

Failed to compete with Google’s ad-serving platforms due to technical instability and insufficient innovation.

WHAT WENT WRONG

  • Platform suffered from reliability issues during high-volume campaigns

  • Poor feature differentiation from competitors

SIGNALS MISSED

  • Rising customer churn due to performance issues

  • Lack of meaningful new features for large clients

HOW COULD THEY HAVE AVOIDED THIS

  • Investing in backend scalability for high-volume campaigns

  • Differentiating with unique features like advanced targeting

TEAMS INVOLVED

Product, Engineering, QA, Marketing

Google AdSense for Mobile Apps

AdTech

Google

Struggled to generate meaningful revenue for publishers due to low-quality ad placements and intrusive formats that frustrated users.

WHAT WENT WRONG

  • Poor alignment of ad placements with user experience in apps

  • Ineffective targeting algorithms for mobile ads

SIGNALS MISSED

  • Negative feedback from developers about low revenue

  • User complaints about intrusive ads decreasing app engagement

HOW COULD THEY HAVE AVOIDED THIS

  • Testing ad formats that balance revenue with user experience

  • Developing better targeting algorithms for mobile audiences

TEAMS INVOLVED

Product, Engineering, Sales, Customer Success

Drift Video (Early Versions)

MarTech, AdTech

Drift

Video marketing tool failed due to poor performance analytics and lack of integration with major CRM platforms.

WHAT WENT WRONG

  • Weak analytics for video engagement tracking

  • Poor integrations with existing MarTech stacks

SIGNALS MISSED

  • Customer complaints about lack of meaningful data insights

  • Low integration rates with popular CRMs

HOW COULD THEY HAVE AVOIDED THIS

  • Partnering with CRM platforms for seamless integration

  • Enhancing video analytics capabilities

TEAMS INVOLVED

Product, Engineering, Customer Success

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