Ep 33: Leading with Purpose: How to Navigate Uncertainty, Change and Growth

Timestamps:

01:19 The Unplanned Path: From Big Names to High-Growth Startups

03:03 Learning from the Giants: The Benefits of Big Company Experience

04:13 Managing Yourself: The Foundation of Leadership

07:01 Playing the Long Game: Balancing Sprints with Sustainability

10:32 Building Cross-Functional Cohesion: The Power of Teaming

14:58 Leading with Purpose: Connecting the Dots for Your Team

20:39  Adapting Your Leadership Style: From Experience to Facilitation

32:24  Embracing AI: The Future of Sales Leadership

The Unplanned Path: From Big Names to High-Growth Startups

I'd love to tell you that my career was carefully mapped out, with each move strategically planned, but the truth is, it wasn’t. My journey into the world of high-growth companies happened more organically than deliberately. Early on, I found myself at Rational Software, which was later acquired by IBM. While IBM was a great environment, it felt a bit too big for my liking. I made the leap to BA Systems, only to have it acquired by Oracle.

Through these experiences, I realized I was more drawn to mid-sized and earlier-stage companies. There’s something more exhilarating about working in a smaller, more agile environment. In these settings, you’re not just a cog in the machine—you’re actively shaping the direction of the company.

Learning from the Giants: The Benefits of Big Company Experience

Starting in big organizations like IBM and Oracle gave me a solid foundation. These companies have a lot of sophistication in their approach to the market—everything from industry solutions to partner ecosystems and sales specialization is handled with a level of depth that’s hard to match. They also invest heavily in training and development, which is something smaller companies often struggle to do as well.

But it’s not just about the systems and training. Being in a big company helps you understand what a future state might look like. When you transition to a smaller organization, you can draw on that experience to navigate your way toward becoming a bigger, more established player. Every small company aspires to grow, and having that big-company perspective can be invaluable.

Growth Opportunities: The Journey from Challenger to Market Leader

One of the most exciting parts of working at a company like ServiceNow is the opportunity for growth. We started off as a young challenger in the mid-market, attacking the space with a lot of energy and innovation. Over time, we grew into a major player, meeting with CEOs and ministers, and making a real impact on society.

Seeing a company go through these phases is incredibly rewarding. But it’s not just about being there for the ride—you need to understand how to navigate each stage of growth. My experience in bigger companies gave me a sense of how to play the long game, how to build resilience and stamina for the journey ahead.

Managing Yourself: The Foundation of Leadership

Before I moved into people management, I did an MBA, and one piece of advice from a lecturer stuck with me: “If you want to manage people, you’ve got to be able to manage yourself.” It’s a simple truth, but it’s also profound. Every day, I start by checking in with myself—am I feeling agitated? Tired? Happy? Being self-aware is the first step in managing the pressures of leadership.

When the pressure mounts, it’s easy to let things like exercise and family time slip, but that’s when you need them the most. If you start cutting back on sleep, it’s a clear sign that something’s wrong, and it’s time to recalibrate. Managing yourself well is crucial for leading your team effectively.

Playing the Long Game: Balancing Sprints with Sustainability

One of my CROs once said, “Every quarter is the most important quarter in the company’s history.” It’s true—there’s always pressure to perform, and each quarter feels like a sprint. But leadership isn’t just about winning the sprint; it’s about running a marathon. You’ve got to build resilience and think about the long game.

In a high-growth company, there will always be another stage to conquer, another challenge to face. You can’t afford to burn yourself—or your team—out in the process. It’s about having a vision for the future and guiding your team on a sustainable journey.

Building Cross-Functional Cohesion: The Power of Teaming

In a sales leadership role, especially in our region, you often find yourself working in a matrixed environment. You might have direct control over your sales team, but you also need to collaborate with marketing, channel partners, and other functions that don’t report to you directly. Building strong cross-functional links is critical to success.

One advantage we have in our region is that we’re on an island—literally and figuratively. This makes it easier to build cross-functional teams because we need to rely on each other more. I’ve seen this play out in many companies, and it’s one of the reasons why cross-functional cohesion is one of our strengths.

Leading with Purpose: Connecting the Dots for Your Team

One of the challenges in leadership is ensuring that everyone on the team understands not just what we’re doing, but why we’re doing it. It’s easy to get bogged down in the day-to-day grind, but without a clear sense of purpose, motivation can wane.

At ServiceNow, during a period of rapid growth, we placed a strong focus on retention and team cohesion. It wasn’t just about hitting targets—it was about creating an environment where people felt connected to a larger purpose. Whether it’s the impact we’re making on customers or the personal goals of each team member, it’s important to connect the dots and make sure everyone knows why their work matters.

Adapting Your Leadership Style: From Experience to Facilitation

As the role of a leader evolves, so too does the way we lead. In the past, leadership was often about drawing on experience—knowing what’s likely to happen based on what’s happened before. But today, things are moving too fast for that to be enough.

I’ve found that facilitation and collaboration are becoming more critical. It’s not just about what I know; it’s about bringing together the right data, insights, and perspectives from the team to make informed decisions. Experience is still valuable, but it needs to be combined with data-driven decision-making to guide the organization effectively.

Embracing AI: The Future of Sales Leadership

AI is no longer just a buzzword—it’s here, and it’s transforming the way we work. I’ll admit, I was initially skeptical, but I’ve had an “aha” moment in the past few months. AI is not just something for the IT team to worry about—it’s something that can profoundly impact sales and go-to-market strategies.

I’ve started leaning into AI, learning how to write prompts and use the tools available to me. It’s been a fascinating journey, and it’s also made me realize that as a leader, I need to stay on top of these developments. AI is changing the way we do research, target customers, and even manage our teams. The future of sales leadership will be shaped by those who can harness the power of AI to work smarter, not harder.

Balancing Change with Stability: The Art of Knowing What to Keep

Change is constant, especially in a high-growth company. But not all change is good. One of the biggest lessons I’ve learned is the value of stability. In a world that’s constantly pushing for more tweaks, more optimizations, it’s important to know when to hold back.

Yes, we could make changes that might optimize performance by a few percentage points, but sometimes it’s better to keep things stable—whether it’s keeping a rep on the same set of accounts or sticking with a proven strategy. Continuity is crucial because people can only absorb so much change before they burn out. As leaders, we need to be thoughtful about the changes we make and ensure that they’re meaningful enough to justify the disruption.

Summary

In navigating the ever-evolving landscape of high-growth companies, the key to effective leadership lies in a balance of self-management, clarity of purpose, and adaptability. 

Drawing from experiences in both large corporations and agile startups, it's clear that success is as much about the journey as the destination. By embracing data-driven decisions, fostering cross-functional collaboration, and leaning into new technologies like AI, leaders can guide their teams through change with confidence. 

Ultimately, it's about creating a stable, supportive environment where both individuals and organizations can thrive.

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