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 away
• What she thought she’d find in healthcare that sales lacked
• The unexpected clarity and motivation that came from stepping away
• And what it really takes to come back, rebuild, and succeed on your own terms

It’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.