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.