Many leaders will happily talk for 45 minutes about their product… and struggle to talk for two about their prospecting engine. In this episode of Why Did It Fail?, Gabe Lullo, CEO of Alleyoop, joins Shivan to unpack why that gap quietly kills startups and stalls growth in mid-market and enterprise sales teams.

Gabe shares stories from decades in the trenches: SDRs who couldn’t make it past lunch, weeks of zeros on the whiteboard, clients who raised millions and still ran out of runway, and what changes when you treat prospecting with the same seriousness as product. He breaks down how Alleyoop makes over a million dials a month and how his team uses AI as a sparring partner to prepare reps for the only 9-10 objections that really matter.

Gabe offers a clear challenge: if you obsess over building the product but take a casual approach to go-to-market, you’re betting the company on hope. He explains when it makes sense to outsource SDR, how to instrument your sales engine like an F1 car, and why the founders who win are the ones who own the front end of the funnel.

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 shares the mindset and practical steps that helped him rebuild, and how that experience now shapes the way he leads, hires and coaches revenue teams.

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 how reaching out for help changed everything, how she rebuilt her approach around intentional accounts, proper research and multi-channel outreach, and what a genuinely good cold call looks like now.

Ayah also shares how this phase shaped her resilience, mindset and confidence, from handling constant objections to nurturing accounts “like little babies” instead of burning through them. If you’re an SDR leaning on spray and pray to hit your number (or managing a team who are), this conversation is a sharp, honest look at why that approach fails long term — and how to replace it with something that actually scales.

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.