WinLossWeek Why High Performing Sales Teams Embrace Win Loss Analysis

Key Takeaways

Background and Experience:

  • The speaker has over 20 years of experience in B2B sales and marketing.
  • Worked at renowned organizations like McKinsey, PricewaterhouseCoopers, Adobe, Qualtrics, and Snap Finance.
  • Currently runs Unicorn Revenue Operations, advising companies on reaching unicorn status via effective revenue operations.

Importance of Win-Loss Programs:

  • Win-loss programs are vital for understanding why deals are won or lost.
  • Qualtrics implemented such a program to improve their sales process, marketing, product feedback, and customer relationships.

Starting a Win-Loss Program:

  • Begin with a small pilot, such as 15-30 interviews.
  • Use a mix of qualitative (interviews) and quantitative (surveys) feedback.
  • Engage a third-party for interviews to ensure objectivity and candid feedback.

Overcoming Challenges:

  • Sales teams may initially be indifferent or resistant due to fears of intrusion or criticism.
  • It's crucial to demonstrate how win-loss insights can help improve their win rates and garner support from the C-suite.
  • Streamline the process for selecting deals to be evaluated and start feedback mechanisms quickly to avoid losing valuable insights.

Elements of a Successful Program:

  1. Mix of Qualitative and Quantitative Feedback: Interviews supplemented with surveys.
  2. Use of Third-Party for Interviews: Ensures unbiased and candid feedback.
  3. Efficient Process: Quick turnaround from deal closure to feedback collection.
  4. Strategic Delivery of Insights: Share insights across the organization to drive cross-functional improvements.
  5. Incremental and Scalable: Start small and expand as you gather success and buy-in.

Benefits of Win-Loss Programs:

  • Truthful Customer Insights: Understand the real reasons behind wins and losses.
  • Coaching and Enablement: Provides specific feedback for individual sales reps.
  • Resource Justification: Helps in securing additional resources by backing claims with customer data.
  • Cross-Functional Impact: Influences different departments such as product development, marketing, and sales strategy.
  • Brand Impression: Shows prospective customers that the company values their feedback, keeping future opportunities alive.

Practical Insights:

  • Initial challenges include budget, process setup, and sales team support.
  • As programs mature, they deliver actionable insights that can justify their cost many times over.
  • The ability to directly impact product decisions and marketing messages has broad organizational benefits.

Final Thoughts:

  • Win-loss programs should be a core part of any revenue operations strategy.
  • Starting small, demonstrating immediate benefits, and gradually scaling up can lead to sustained success and organizational alignment.

Visual Aids (Summary Slides):

  • Keys to an effective program, potential roadblocks, and primary benefits were summarized in visual slides to complement the discussion.


  • Effective win-loss programs require initial investment and strategic alignment but offer substantial returns in terms of improved sales processes, product feedback, and overall market understanding.

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