The Leadership Blueprint: Key Traits for CXOs to Drive Success

In this episode of Future Focused CXOs, we had the privilege of speaking with Will Urban, former Chief Revenue Officer at Flexport and now an advisor at R7 and Companion Ventures. With decades of experience in supply chain management and venture capital, Will offers invaluable insights into leadership, growth, and how to balance the demands of a high-level career with family life.

One of the most powerful lessons from our conversation with Will was the idea that leadership isn’t just about strategy or metrics—it’s about people. Will emphasized that true leadership requires prioritizing the well-being and success of your team over personal achievements. Leaders who build trust and loyalty within their teams empower people to reach their full potential.

Adaptability plays a central role in Will’s leadership philosophy. In a rapidly evolving business environment, being able to adjust strategies based on feedback is vital. Will also stresses the importance of transparency—open, honest communication with team members helps create an environment of trust. As a leader, it’s essential to be accessible, approachable, and willing to admit when something isn’t working. This not only strengthens relationships within teams but also enables businesses to evolve and grow.

Having transitioned from a corporate leadership role to venture capital, Will brings a unique perspective to assessing startups and high-growth companies. His experience at Flexport, where he helped scale the company from $600 million to nearly $5 billion in just three years, informs his approach to evaluating businesses for investment.

For CXOs interested in venture capital or startups, Will’s advice is clear: look for strong leadership first and foremost. While product-market fit and the go-to-market strategy are undeniably important, a great leader is often the deciding factor in whether a company will thrive. Will’s approach to evaluating founders goes beyond metrics—it’s about understanding their leadership capabilities, their ability to navigate challenges, and their willingness to listen to feedback. He also places great importance on financial stewardship—successful companies manage investor capital responsibly, showing frugality rather than stinginess. This inspires confidence among stakeholders and supports sustainable growth.

In venture capital, Will highlights the significance of cultural due diligence. This is often an overlooked aspect of evaluating investment opportunities. Will believes that cultural alignment is a key predictor of a company’s long-term success. Startups and scale-ups with strong, transparent cultures are more likely to attract top talent, adapt to market changes, and build lasting customer relationships. For CXOs, this lesson is invaluable—whether you’re managing a team or evaluating potential investments, understanding the underlying culture of an organization can be just as important as analyzing financials.

One of the most personal and relatable aspects of our conversation with Will was his reflection on balancing a demanding career with family life. Over the years, Will realized that his intense focus on work had begun to affect his personal life and well-being. He made a conscious decision to step back, prioritize time with his family, and seek a career path that allowed for more flexibility.

For many CXOs, the demands of leadership can lead to burnout if family life is neglected. Will’s story is a powerful reminder that professional success should not come at the expense of personal happiness. He advocates for strategic time management, ensuring that both career and family commitments are balanced effectively. By prioritizing his family, Will found a new sense of fulfillment that not only improved his personal life but also boosted his effectiveness in his professional endeavors.

For mid-career professionals looking to accelerate their careers, Will offers several key pieces of advice:

The conversation with Will Urban offered more than just business insights—it was a masterclass in leadership, personal growth, and the importance of maintaining a balanced life. Will’s perspective on leadership highlights the importance of people-first thinking, adaptability, and transparency. His advice on venture capital offers a nuanced approach to assessing startups, focusing on leadership and cultural alignment alongside financials. And his journey toward finding a work-life balance is a valuable lesson for any executive.

Whether you’re an aspiring CXO, a venture capitalist, or someone navigating the challenges of career progression and family life, this episode provides actionable insights that can help you lead with purpose, scale your business effectively, and live a more fulfilling life.

If you missed the episode, don’t worry—these key takeaways will help guide your leadership decisions, but listening to Will’s full interview offers even more in-depth strategies and real-life examples that you won’t want to miss.