Episode 14

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Published on:

12th Nov 2025

The Wake-Up Call That Changed Shiwam Singh’s Sales Career

Imagine landing your first sales job and losing it just months later.

That was the reality for Shiwam Singh, now an SDR at Cognism. In this episode of Why Did It Fail?, Shiwam opens up about the sting of his first big setback in tech sales, how it shook his confidence, and the lessons he carried into his second chance at Cognism.

From rebuilding his mindset to learning the power of listening, discipline, and feedback, Shiwam’s story is a reminder that failure isn’t the end, it’s the reset you sometimes need.

If you’ve ever doubted whether you’re cut out for sales, this one’s for you.


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About the Podcast

Why Did It Fail?
A Sales Podcast
Welcome to Why Did It Fail?, a series 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 sales leaders, founders, and operators, we unpack what went wrong and more importantly, what they learned from it. No fluff, just failures that made them better.