Ep 36: Fail Fast, Fail Forward: The Key to Thriving in High-Pressure Sales and Leadership

Timestamps:

02:24 From Cricket to Tech Sales: A Journey of Serendipity

02:59 Why Team Sports Prepare You for Business (More Than You Think)

04:31 The Pivot to Tech Sales: A Lucky Break or a Calculated Move?

05:49 From Sales Rep to Leader: The Mental Shift

07:27 The Art of Building High-Performance Teams

09:30 How to Spot a Bar-Raiser in Your Team

20:17 Eating the Frog: Why Doing the Hardest Thing First Matters

23:13 Why Ownership Beats Talent Every Time

29:51 Radical Candour: The Key to Authentic Leadership

24:56 Fail Fast, Fail Forward: Iteration is Everything

About Alex Palmer:

Alex Palmer is the SMB Manager - ANZ at Deel, a hyper-growth Pre-IPO SaaS company transforming payroll and workplace mobility worldwide.

Originally from the UK, Alex came to Australia to play cricket professionally. His mindset as an athlete - always getting better while competing carries over into his sales and leadership career.

He’s all about creating a safe space where his team can take risks and grow, and he practices "Radical Candour," being upfront and honest whether the news is good or bad.

Alex is a coach at heart and volunteers time mentoring business owners and sales talent through organisations like Rare Birds and Early Work.

From Cricket to Tech Sales: A Journey of Serendipity

I didn’t plan on being where I am today—leading teams in high-growth tech companies. My story started on a cricket field. I moved from the UK to Australia not to build a sales career but to play cricket for a few months. A simple "yes" to that opportunity changed everything. Cricket taught me a lot about teamwork, discipline, and strategy. But the biggest lesson was the power of saying yes to the unknown. That’s what brought me into tech sales and, eventually, leadership. Sometimes, the best opportunities come disguised as a bit of fun.

Why Team Sports Prepare You for Business (More Than You Think)

I’ve always believed that team sports prepare you for life. I’ve been immersed in team sports since I was six, and they’ve shaped who I am today. The principles are surprisingly simple but hard to master: commitment, training, and building a high-performance culture. You win as a team and lose as a team—no exceptions. In business, everyone needs to know what "good" looks like and continuously strive to improve. It’s not just about being good yourself; it’s about helping everyone around you improve. That’s the secret to building winning teams on a field or in an office.

The Pivot to Tech Sales: A Lucky Break or a Calculated Move?

People say I’m lucky. Maybe they’re right, but I also believe you make your luck. After my cricket stint, I needed a job to stay in Australia. A friend from the cricket club helped me land a role at Uber, pre-IPO. I didn’t realise at the time how massive this opportunity was, but I knew one thing—I love talking to people, understanding their problems, and solving them. Tech sales was a natural fit. Fast, growing, and unpredictable, much like the sports I grew up with. If you enjoy adapting on the fly, you’ll thrive in this world.

From Sales Rep to Leader: The Mental Shift

Moving from an individual contributor (IC) to a leader is a different ball game. As a rep, you control your inputs and outputs. If you work hard, you’ll see the results. But as a manager, you don’t have that direct control. You must let go, trust your team, and focus on getting the best out of them. That’s the real challenge—how do you build a culture where everyone feels empowered to do their best work? At Uber, I learned that adaptability is key. Managing a team of 50 is not the same as managing a team of 5. You need to adjust your methods, frameworks, and mindset to get the best out of people.

The Art of Building High-Performance Teams

I’ve worked in companies like Uber and Deel, where hypergrowth is the norm. The biggest challenge isn’t just keeping up with the pace; it’s designing teams that can thrive in chaos. At Deel, we compete with massive HR and payroll software players. What’s exciting is the constant need to redefine processes that worked yesterday but won’t work tomorrow. The trick? Building a culture where people feel like they’re part of something bigger than themselves and hiring people who are natural bar-raisers. You don’t just need good performers but people who will elevate the entire team.

How to Spot a Bar-Raiser in Your Team

I often get asked, “What do you look for in a sales hire?” It’s simple—EQ, IQ, curiosity, and drive. You're already ahead if you can understand people (EQ) and apply intelligent solutions (IQ). Curiosity drives you to ask better questions, leading to better outcomes. Lastly, drive. I want people who light their candle. If I need to be the one motivating you every day, we’ve got a problem. Sales is hard enough without dragging people along.

Eating the Frog: Why Doing the Hardest Thing First Matters

We’ve all heard of "eating the frog," the idea that you should tackle the hardest task first. For me, this has always been key, whether I was a rep or a manager. It’s easy to push the hard stuff to the end of the day, but that only makes it harder. At Uber, we had a saying: “Get your 50 dials done before lunch, and the rest of the day will feel like a breeze.” As a manager, I followed this rule, too. I’d often take on tasks my boss didn’t want to do, not because I had to, but because I knew it would make me better. It’s a mindset that helps you progress from IC to leadership—doing the work others shy away from.

Why Ownership Beats Talent Every Time

You can be the most talented salesperson in the world, but you won't get far if you don’t take ownership of your results. I’ve had to let go of highly experienced reps because they were like Ferraris with no fuel in the tank. Talent only takes you so far. The best salespeople are the ones who take full responsibility for their performance. If they’re not hitting their targets, they don’t make excuses—they make changes. Whether improving their openers or making more calls, they figure it out.

The Duck and Eagle Theory: Managing Different Types of Performers

At a recent sales kickoff, we used an analogy that stuck with me: the Duck and Eagle theory. In any team, you’ll have ducks—people who waddle along, get to 100%, but never soar. Then you have eagles, the high performers who consistently fly above the rest. As a leader, your job is twofold. You need to train the ducks to reach a baseline level of performance while also nurturing the eagles to fly even higher. Not everyone will be an eagle, but even a duck can waddle faster with the right support.

Radical Candor: The Key to Authentic Leadership

Radical candour has been a game-changer for me. I first encountered the term when a manager at Uber called me out for writing an overly formal email. He said, “Who wrote this? It doesn’t sound like you.” That feedback stuck with me. It’s about being upfront and calling a spade a spade. Whether it’s good or bad news, you must be transparent. I’ve found that people appreciate honesty, even when it’s hard to hear. When you lead with radical candour, you create an environment where people feel safe to fail but also know where they stand.

Creating Psychological Safety in High-Pressure Sales Environments

Sales is a pressure cooker, especially in tech, where the stakes are high, and the pace is relentless. One of my core principles as a leader is creating psychological safety. People need to feel like they can take risks without fearing the worst. Risk in sales shouldn’t be a gamble; it should be calculated with a clear upside. If my team knows I have their back, even if things don’t go as planned, they’re more likely to push boundaries and innovate. And when they succeed, I’ll be their biggest cheerleader.

Fail Fast, Fail Forward: Iteration is Everything

One of the best advice I’ve received is to "fail fast and fail forward." In tech sales, you won’t always get it right the first time. The key is to iterate quickly—whether it’s your call script, objection handling, or even your team management style. At Uber, we constantly tweaked our processes. What worked last month might not work this month, and that’s okay. The faster you accept failure and learn from it, the quicker you’ll find success.

Summary

Leadership in tech sales is about embracing chaos, building teams that thrive under pressure, and fostering a culture of ownership and radical candour. My journey from cricket fields to boardrooms has taught me that success doesn’t come from avoiding challenges but from tackling them head-on. Whether you’re a rep or a leader, the principles remain the same—take ownership, iterate quickly, and always strive to raise the bar.

Hiring or replacing someone in the next 90 days?

We partner with tech sales leaders who are time-poor and under pressure and introduce them to top performers without wasting time or risking average hires so that they can build winning teams and careers.

Message [email protected] today