Claim OwnershipWhy Did It Fail?
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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.
102 Episodes
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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, and he never even knew it was on the table.Shivan and Gearoid unpack exactly how tunnel vision, target pressure and “just be grateful for the deal” thinking can quietly cost reps career-defining opportunities. Gearoid breaks down the difference between perception and perspective, why it never costs you to ask one more question, and how he now coaches sellers to mine existing accounts properly instead of behaving like “new logo magpies.”If you’ve ever chased the close so hard you forgot to understand the customer, this one will sting in all the right ways, and leave you with practical mindset shifts around discovery, attitude and actions that you can take into your next deal.
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 mentally checked out, and the simple mindset shift that transformed how he runs discovery, asks questions and earns trust. It’s a sharp, honest, deeply practical conversation for anyone who knows they slip into feature-dumping mode and wants to break the cycle.A must-listen for reps and leaders who want to sell with curiosity, not ego, and avoid making the same mistake Bryan did.
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, and learned to separate his self-worth from the outcome of a call. He reflects on the moment things finally clicked, why nurturing early conversations changed everything, and how those difficult months shaped the empathetic leader he is today.A must-listen for anyone who’s ever stared at the phone and wondered whether they’re cut out for sales. James shows exactly how shaky starts can become the making of a great career.
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 between pressure management and expectation management.Listen now to learn how Junis turned a crash into a comeback.
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.
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 by vertical and country, he shares the frameworks that turn expansion plans into scalable revenue engines.If you’ve ever struggled to define your target customer, or you’re planning to take your sales motion international, this conversation is a masterclass in narrowing focus, aligning strategy, and landing faster in new markets.
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 by a hot lead, or you’re moving from prospecting to closing, this conversation is a masterclass in qualifying deeper, multi-threading smarter, and managing your own mindset.
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, and succeed on your own termsIt’s a story about trusting your gut, reshaping your identity, and learning to make career decisions that serve you, not other people’s expectations.Listen now to hear how Nia’s ‘wrong turn’ ended up giving her the fuel to get further ahead than ever.
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 non-negotiable if you want a career that lasts.
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, misreading motivation, and how to have tough conversations without losing your team. If you’re stepping into sales management, or already navigating that tricky balance of people and performance, this episode is packed with honest lessons that can shape your approach.
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 quarter might be slipping.If you’ve ever struggled to keep your activity high and your pipeline healthy after a big career move, this conversation is packed with insights you can act on straight away.
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 inside a fast-moving sales org, this episode is full of insight you’ll want to take with you.
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 recognition didn’t come, this episode is a reminder that your path is still valid and that you can become stronger for it.
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, this episode is packed with real-talk, reassurance, and practical takeaways you’ll want to carry with you.
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.
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 starting out, managing a team, or feeling stuck.
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 lessons on growth, self-awareness, and what really matters when leading a team and building a life.
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.
This week we’re flipping the script and looking at outbound through a post-sale lens. Evan Nelson, VP of Customer Experience at Cognism, sits down with Natasha Evans, VP of Customer Growth at Hook, to explore how Customer Success can become a true driver of revenue. They dive into how principles from traditional outbound sales are deeply relevant in customer success, why CS teams should think like sellers, and how growth is increasingly coming from existing customers.
Cognism’s VP of Sales Development, Catherine Olivier, sits down with David Wilkins to unpack what it really takes to be an impactful SDR leader in today’s sales landscape. They dive into the difference between good and great SDR teams, how to build high-performing teams from the ground up, and why strong leadership is about more than just tracking activity. David shares practical advice for SDR leaders navigating change, scaling teams, and standing out in an increasingly competitive market.
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