When the Chief Customer Officer role first emerged in SaaS, Alexis Hennessy was already there—helping define it. Twelve years ago, she co-founded the post-sales executive search practice inside Heidrick & Struggles, one of the world’s premier search firms. She witnessed the rise of the CCO, the collapse of the role during the downturn, and now the fastest resurgence the market has seen in years.

In this episode, Alexis breaks down why retention has become existential, why CCO hiring has spiked again, and what the best CCO candidates consistently do to stand out. She details the patterns behind successful hires, the emergence of consumption and AI-driven operating models, and why the path from CCO to CEO may finally be opening wider than ever.

A practical and unfiltered look into the future of post-sales leadership—from the person helping shape who gets the top jobs.

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Timestamps

0:00 – Preview & Introduction

1:22 – Meet Alexis Hennessy: Partner at Heidrick & Struggles

2:02 – Many CEOs Still Don’t Know What They Want

4:10 – What CEOs Want in a CCO

5:16 – What Great CCO Candidates Do in Interviews

6:15 – Why CCO Hiring Is Surging Again

7:25 – What Sets VP Candidates Apart When They Want to Move Up

9:00 – Are Boards Demanding AI Experience?

10:45 – What the Best CCO Hires Do in Their First Year

12:45 – Personality Traits That Define High-Performing CCOs

13:43 – Agentic AI, Consumption Models & the New Stakes for CCOs

15:23 – Can CCOs Become CEOs?

18:28 – Predictions: The Future of the CCO Role

19:23 – Closing Thoughts

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What You’ll Learn

* Why the CCO role is surging again after a multi-year slump

* The three types of CEOs who hire CCOs—and which ones to avoid

* The interview behaviors that separate top candidates from the rest

* Why “listening first” is the #1 predictor of CCO success

* What VPs need to show to break into the CCO ranks

* The business conditions making the CCO-to-CEO path more realistic than ever

* The critical KPIs great CCOs build to influence their executive peers

* How consumption and agentic AI models increase the strategic importance of retention

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Check out the Key Takeaways & Transcripts: https://www.gainsight.com/presents/series/unchurned/

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Where to Find Alexis:

LinkedIn: https://www.linkedin.com/in/alexishennessy/

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Where to Find Josh:

LinkedIn: https://www.linkedin.com/in/jschachter/

Paul Shen - natto.dev