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Why Did it Fail

A Sales Podcast

Welcome to Why Did It Fail?, a podcast hosted by Cognism’s Sales Coach, Shivan Pillay.

Each episode digs into the real stories behind deals that fell through, strategies that didn’t land and campaigns that missed the mark.

Through honest conversations with SDRs and AEs, all the way up to sales leaders and founders, we unpack what went wrong and, more importantly, what they learned from it. No fluff, just failures that made them better salespeople.

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The Host

If you’re in sales and want to sell smarter, Why Did It Fail? is the podcast for you. Hosted by sales expert and coach Shivan Pillay, each episode turns failure into a lesson worth hearing.

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Shivan Pillay

Shivan Pillay is a Sales Coach and Trainer at Cognism with years of experience helping teams hit their numbers and stay motivated doing it. As host of Why Did It Fail?, he digs into the real stories behind missed targets and tough lessons — uncovering what every seller and leader can learn from failure.

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Messed up? Learned a lot? Let’s talk about it.

We’re always looking for guests with real stories to tell. Join Why Did It Fail? and share the lessons you learned the hard way.

Apply to be a guest on Why Did It Fail?

More Cognism Podcasts

Dive into the full collection of Cognism podcasts. Featuring stories and insights from the experts driving B2B sales, marketing, and RevOps forward. Whether you’re here to learn, level up, or just listen in, you’ll find real conversations packed with practical takeaways.

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Marketing Dilemmas

From demand gen to creative strategy, this series tackles real marketing challenges. Hear honest, practical advice from experts who’ve faced the same struggles — and learn how to turn your own dilemmas into opportunities for smarter growth.
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Diary of a first-time CMO Volume 1
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Diary of a First-Time CMO – Volume 1

Follow Alice de Courcy’s four-year journey from $5M to $40M ARR. In 63 candid entries, she shares the wins, missteps, and lessons that shaped Cognism’s rise — and what every marketer can learn from scaling fast without losing focus.
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Diary of a first-time CMO volume 2
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Diary of a First-Time CMO – Volume 2

Alice returns with 50+ new lessons from her path to $100M ARR. From expanding into new markets to launching products and leading change, she shares raw, practical insights on what it takes to grow — and stay grounded doing it.
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The RevOps Review

Keep your revenue engine running smoothly with insights from RevOps pros. Hear how top operators optimise systems, fix data friction, and scale processes that fuel predictable growth across fast-moving B2B teams.
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Join the conversation

See what listeners say about Why Did It Fail?,  and join the conversation yourself.

Share your takeaways, aha moments, or favourite episodes using #WhyDidItFail and be part of the growing B2B sales community.

Loved the podcast? Keep learning!

Head to the Cognism SDR Zone for tips, tools, and talk tracks that help top-performing reps, like you, book more meetings.

Explore the SDR Zone