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PODCAST

Why Did It Fail?

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.

business management

All Episodes

24:07

Staying Too Long: How Redundancy Reset Stuart...

Why Did It Fail? ·

2026/02/04

In this episode of Why Did It Fail?, Stuart Taylor, CRO at The Lennox Academy, opens up about a failure most people only talk about in whispers: staying at a company too long after an acquisition… and being made redundant as a result. He talks candidly about what it felt like in the moment, the shock, the hit to his identity and much more.Stuart and Shivan dig into the uncomfortable truth about loyalty, timing your exit, and recognising when a role or company has stopped serving your growth. Stuart

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18:05

From Spray and Pray to Strategic: How Ayah...

Why Did It Fail? ·

2026/01/21

When Ayah joined Cognism, she didn’t know what an SDR was, but she knew how to hustle. Her first few months were a blur of spray-and-pray dialling: huge lists, minimal research, mass calls… and 400% of target in month one. It worked. Until it really didn’t.In this episode of Why Did It Fail?, Ayah sits down with Shivan to unpack the dark side of spray and pray: the stress, the lack of control, the low-quality pipeline and the moment she realised her “success” wasn’t sustainable. She talks through

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24:57

The Deal That Shrunk: How Gearóid Cox Lost a...

Why Did It Fail? ·

2026/01/07

In this episode of Why Did It Fail?, Gearoid Cox, Founder and CEO of Sales Pipeline, shares the story of a deal that looked like a win on paper, but turned out to be a brutal lesson in discovery. As a young enterprise rep, Gearoid was laser-focused on getting the PO signed. He closed what he thought was a big hardware sale… only to find out later it was the tiniest slice of a huge, multi-layered project. The rest of the business, software, print, additional hardware, went straight to competitors,

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24:23

When Impressing the Buyer Lost the Deal: Bryan...

Why Did It Fail? ·

2025/12/17

Sales coach Bryan Mulry joins Shivan to break down a failure most sellers secretly recognise: talking too much, listening too little, and trying far too hard to impress. Bryan shares the painful moment he realised he’d spent 87% of a call pitching to a VP of Sales who didn’t even have the team he was selling to, and how that single conversation exposed a habit that had been costing him deals for years.In this episode, Bryan unpacks why sellers default to “show and tell,” how to spot when a buyer has

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24:12

Hands Shaking on Every Dial: How James Greene Beat...

Why Did It Fail? ·

2025/12/10

When James Greene first stepped into sales, cold calling hit him harder than he expected. Every dial came with shaking hands, spiralling doubt and the pressure to prove he belonged. Rejection felt personal, missed targets knocked his confidence, and one complaint from a prospect nearly convinced him to walk away from the job entirely.Now Global Business Development Manager at Bounce Insights, James talks to Shivan Pillay about how he rebuilt his mindset, found resilience through Brazilian Jiu-Jitsu,

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24:51

From Top Seller to Burnout: The TRAP New Sales...

Why Did It Fail? ·

2025/11/26

When Junis Seger stepped into his first Head of Sales role, he thought he was ready for anything.After all, he’d just come off back-to-back President’s Club wins, smashed targets as an AE, and built a reputation as one of the best in the business. But leading a fast-growing startup was different.Suddenly, he was juggling investor targets, founder expectations, team management, and his own impossible standards, all at once.The result? Burnout, blurred boundaries, and a harsh lesson in the difference

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17:37

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

Why Did It Fail? ·

2025/11/12

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

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27:45

The ICP Trap: Why Most Expansion Strategies Fail in...

Why Did It Fail? ·

2025/10/29

When tech companies expand into Europe, most assume their home-market success will follow them across borders. But for Rick Pizzoli and his team at Sales Force Europe, one lesson has repeated itself over 500 launches, a vague ideal customer profile can quietly derail even the best go-to-market plans.In this episode of Why Did It Fail?, Rick unpacks how unclear ICPs lead to wasted spend, internal misalignment, and slow traction, and how to fix it fast. From building consensus across teams to pivoting

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19:25

How to Transition From SDR to AE With Ease Featuring...

Why Did It Fail? ·

2025/10/15

As an SDR-turned-AE, Sonya Kuci thought she’d landed the dream opportunity, an inbound ICP lead with the decision-maker on the first call, smooth comms, and a live trial underway. But just before close, everything unravelled.In this episode of Why Did It Fail? Sonya unpacks the hard lessons from losing a “can’t-miss” deal: the hidden risks inside inbound opportunities, how to spot green flags disguised as red ones, and what SDRs need to know before stepping into AE life.If you’ve ever been ghosted

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30:24

The Wrong Call: What Nia Secker Learned from Leaving...

Why Did It Fail? ·

2025/10/01

What happens when you leave a role you actually loved?In this episode, Nia Secker, SDR Manager at MySalesCoach, opens up about the moment she left sales to pursue a more “traditional” path, only to realise just how right sales had been all along.Nia and Shiavn unpack:Why the pull to “use her degree” felt strong enough to walk awayWhat she thought she’d find in healthcare that sales lackedThe unexpected clarity and motivation that came from stepping awayAnd what it really takes to come back, rebuild,

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35:40

Resilience, Mindset, and the Power of Coaching with...

Why Did It Fail? ·

2025/09/17

After 23 years in corporate London, Niraj Kapur left to start his own coaching business - only to discover that the world didn’t care about his past awards or big-name employers. In this candid conversation, he shares the struggles of rebuilding from scratch in his mid-40s, navigating divorce, health challenges, and a global pandemic. Niraj opens up about resilience, why sales success is more mindset than method, and why investing in yourself (with the right coaches, mentors, and habits) is

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33:59

Coaching, Trust and the Cost of Misreading Your Rep...

Why Did It Fail? ·

2025/09/03

In this episode, Shivan is joined by Sian Taylor, Sales Manager at Klaviyo, for a candid conversation about one of the most overlooked responsibilities in leadership, understanding your reps before you coach them.Sian shares a pivotal early management mistake: focusing on performance metrics instead of the person behind them. The result? A damaged relationship, a loss of trust, and a painful rebuild that taught her how much leadership really hinges on empathy.They discuss coaching blind spots,

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17:48

Getting Past Missing Quota for the First Time with...

Why Did It Fail? ·

2025/08/20

In this episode, Shivan chats with Johnny Stiffell, Commercial AE at Cognism, to talk about his first real dip in performance, and the lessons it left behind.From moving up into a new role without a ramp period to juggling longer sales cycles, self-generated pipeline, and the return of daily cold calling, Johnny shares what it’s like to navigate that tricky adjustment period.They dig into prospecting habits, the mindset shift needed when the inbound slows, and how to spot the early signs that your

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20:53

What Sales Leaders Miss: Strategy, Scale and Internal...

Why Did It Fail? ·

2025/08/06

In this episode of Why Did It Fail?, Shivan is joined by Joe Stubbs, VP of UK Sales at Cognism, for a brutally honest look at what happens when a new process sounds smart, but doesn’t entirely stick.They dig into the early months of Joe’s leadership, where the pressure was high and the ambition was huge. But a well-intentioned rollout exposed some tough truths about enablement, alignment and operational execution.If you’re leading GTM strategy, trying to fix cross-team friction, or navigating change

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43:17

Why Leaving Was the Only Way Up: The Hidden Cost of...

Why Did It Fail? ·

2025/07/23

In this episode, Shivan is joined by Lauren Reeves, Senior BDR Manager at Swap, who shares the emotional weight of building a sales career without ever being internally promoted. From imposter syndrome to self-belief, Lauren opens up about the frustration of being overlooked and the resilience it took to succeed anyway.They dive into the myths around internal progression, the pressure to prove yourself, and why moving on isn’t always a failure. If you’ve ever questioned your value because

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30:39

Hiring, Pressure, and Finding Your Voice in Sales...

Why Did It Fail? ·

2025/07/09

In this episode, Shivan is joined by Brontë Mulvany, Head of Business Development at ComplyAdvantage, who opens up about the high-pressure reality of hiring her first team. From navigating imposter syndrome to learning how to trust her gut, Brontë shares the hard-earned lessons that shaped her leadership style.They talk about clue gathering, courageous conversations, and why copying someone else's leadership playbook just doesn’t work. If you’re stepping into your first management or hiring role,

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22:23

The Cost of Selling to Someone Who Was Never Going to...

Why Did It Fail? ·

2025/06/25

This week on Why Did It Fail?, sales coach Shivan Pillay sits down with Isa Sher, Sales Manager at Cognism, to unpack one of the most pivotal failures of his early sales career. Isa shares how losing a major deal reshaped his approach to qualification, champion building, and managing a high-performing sales team.

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33:56

The Failure That Shaped a Brand New Approach to Sales

Why Did It Fail? ·

2025/06/11

What happens when you don’t pass your sales probation?In this episode, Shivan sits down with Harry Monkhouse to hear the story of how he failed his first SDR probation and turned it into the catalyst for a career in sales leadership.They dig into the mindset shift Harry had to make, the tactical changes that got him back on track, and the three things he'd do differently if he were starting again.It's a brutally honest and massively helpful listen for anyone in sales, especially if you're just

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43:06

The Ego Trap: How Getting Fired Made Chris Ritson a...

Why Did It Fail? ·

2025/05/28

In this episode of Why Did It Fail?, sales coach Shivan Pillay sits down with Chris Ritson, founder, advisor, and sales trainer, for a raw and revealing conversation about the leadership failure that reshaped his life.Chris opens up about the moment he was let go from his first AE leadership role, how unchecked ambition and ego clouded his judgment, and why that painful experience became a turning point. From missed warning signs to rebuilding trust with his closest friends, Chris shares hard-earned

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14:43

When the Vision Doesn’t Match Reality: Michael...

Why Did It Fail? ·

2025/05/14

Welcome to the first episode of Why Did It Fail?, a fresh look on Redefining Outbound! In this episode, Cognism’s Shivan sits down with Narrative AI founder Michael Isernio to unpack a failed VP of Sales stint, exploring why outbound fell flat, how misalignment with leadership signaled deeper issues, and what he’d do differently if given another shot. A candid, insightful look at failure as fuel for growth.

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104 results

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