Navigating the Executive Job Search

In the competitive landscape of executive career transitions, the journey from recognizing the need for change to landing the ideal leadership role can be challenging. Even for highly accomplished professionals, breaking through to the next level often requires more than just impressive credentials and experience.

This was precisely the situation facing Rowan Johnson, a seasoned professional who had been “solidly in the same place at that upper management level for a long time.” Despite leading significant projects and people as an individual contributor, Rowan felt constrained by a glass ceiling that prevented advancement to formal executive leadership.

What followed was a three-year journey that culminated in a successful transition to an executive position. Rowan’s experience offers valuable insights for executives contemplating similar career moves, particularly regarding the importance of persistence, defining personal priorities, and building meaningful professional relationships.

Recognizing the Need for Change

For many executives, the decision to pursue a new role begins with a growing sense that their current position no longer aligns with their career aspirations or personal values. For Rowan, this realization came after years of feeling professionally stagnant.

“I was hitting that glass ceiling…I was leading projects, I was leading people, but as an individual contributor, so I wasn’t getting those direct reports where I felt like I had the ability to mentor and develop people on the level that I wanted to,” Rowan explains.

This frustration will resonate with many senior professionals who find themselves in roles that no longer challenge them or provide opportunities for growth. The desire for “more meaningful and intentional leadership” became the catalyst for Rowan’s career transition journey.

Defining What Truly Matters

One of the most significant revelations in Rowan’s search process was the realization that job specifications were less important than finding the right organizational culture.

“I thought that I needed to nail down what job I wanted. And for me, it was more about the culture I wanted to belong to,” Rowan shares. “I wanted to be seen as my authentic self, and I wanted to belong to an organization where success was celebrated and hardships were carried through together, and no one was punished for making mistakes, but mistakes and risks were encouraged.”

“I sought to find a place where humanity in all of its rawness and individuality was celebrated and we could all grow together.”

This clarity on cultural priorities became Rowan’s “guiding light” throughout the search. By establishing clear priorities—culture first, executive leadership second, and cutting-edge technology third—Rowan created a framework for evaluating opportunities beyond title and compensation.

For executives contemplating a career move, this approach offers a valuable template. By identifying and prioritizing what truly matters to you—whether it’s organizational culture, leadership philosophy, industry focus, or work-life integration—you create a compass that will guide your search toward truly fulfilling opportunities.

Investing in Career Assets

A critical turning point in Rowan’s journey came with the decision to invest in professional career services. After recognizing that standard resume advice wouldn’t suffice for executive-level positions, Rowan engaged with Executive Resume Writers for comprehensive support.

“The last time I took a class on resumes was in college,” Rowan admits, highlighting a common oversight among seasoned professionals. “There are very specific things that folks are looking for that set you apart as someone ready for executive leadership.”

The investment went beyond resume writing to include interview preparation focused on executive presence. These sessions involved “brutal conversations” about poise, presentation, and communication skills that continue to serve Rowan daily in an executive role.

“I get to carry those [skills] into my world now.”

This underscores an important point for executives: career transition services provide value that extends far beyond landing the next position. The skills and insights gained become career assets that enhance your effectiveness as a leader.

The Power of Authentic Connections

Perhaps the most compelling aspect of Rowan’s story is the approach to networking, which challenges conventional wisdom about transactional professional relationships.

Rowan advises. “I never want just to use a connection and think of it as, okay, one day they can do something for me, but we have Christmas together, we go out for drinks, we have lunch, I know their family.”

This authentic approach to relationship-building paid dividends during the interview process. Though Rowan didn’t personally know anyone at the target company, friends and friends-of-friends vouched for Rowan’s character and capabilities.

This perspective offers a refreshing alternative for executives who may feel uncomfortable with traditional networking activities. By approaching professional relationships with genuine interest and investment, you build a community that naturally supports your career journey.

Navigating the Interview Process

When the right opportunity finally emerged, events moved quickly. After an initial recruiter interview, Rowan met with two VPs within days. The entire process took approximately two weeks, culminating in an offer that required a swift decision.

This rapid timeline is increasingly common for executive roles, particularly when organizations are filling critical leadership gaps. Preparing for an accelerated process—practically and psychologically—can be the difference between capturing and missing an opportunity.

Rowan’s decision-making process balanced personal intuition with collective wisdom, consulting with mentors and family members before accepting the position. This collaborative approach to career decisions exemplifies how executive transitions should be treated as a “team sport,” drawing on the insights of trusted advisors who understand your goals and values.

The Reality of Executive Transitions

Seven weeks into the new role at the time of this interview, Rowan offers candid reflections on the challenges of executive transitions. Despite extensive experience, the learning curve in a new organizational culture can be steep.

“Even though I’m an expert in my field, boy, do I feel like a newborn most of the time right now,” Rowan confesses. Adjusting to new acronyms, organizational structures, and communication norms requires humility and vulnerability—qualities that might seem at odds with executive leadership but are essential for building credibility and rapport.

This transparency about the difficulties of transition serves as both reassurance and preparation for executives contemplating similar moves. The path to higher leadership often involves temporary discomfort and uncertainty, even for the most qualified candidates.

Persistence: The Ultimate Success Factor

Perhaps the most valuable lesson from Rowan’s experience is the importance of persistence in achieving executive career goals. The journey from initial recognition of the need for change to successfully landing an executive role took nearly three years—a timeline that tested Rowan’s resolve.

“I considered quitting several times,” Rowan admits. “I thought I just didn’t have the stamina for it anymore.” This candid acknowledgment of doubt and frustration will resonate with many executives who have experienced prolonged job searches.

Yet Rowan’s message to aspiring executives is unequivocal: “If it’s your dream, please don’t give up. People die climbing up this mountain, but it’s worth it if you can just make your way up here.”

In today’s challenging executive job market, persistence often becomes the differentiating factor between success and missed opportunities. Combined with clarity about what you want, persistence creates a powerful formula for achieving your executive career aspirations.

Continuous Leadership Development

During the waiting periods of the job search, Rowan maintained momentum by pursuing leadership development opportunities. This approach served multiple purposes: it kept Rowan engaged and hopeful, developed relevant skills and knowledge, and provided the language and concepts needed to excel in executive interviews.

“I was constantly taking advantage of every opportunity, both inside my company and outside, to take leadership classes, watch keynote speakers, go to conferences, whatever I could to keep learning the language and develop myself,” Rowan explains.

This commitment to continuous learning exemplifies the proactive mindset that distinguishes successful executive candidates. Rather than viewing a job search as a passive waiting game, Rowan used the time to become “the best executive that I can be before I’m actually an executive.”

Key Takeaways for the Executive Job Search

Rowan’s journey offers several actionable insights for executives contemplating or currently engaged in career transitions:

• Define your priorities beyond the job description. Understand what truly matters to you, particularly regarding organizational culture and leadership opportunities, and use these criteria to evaluate potential roles.
• Invest in executive-level career services. Professional support with resume development, LinkedIn optimization, and interview preparation provides value that extends far beyond your immediate job search.
• Build authentic relationships, not transactional networks. Focus on making genuine connections with colleagues and industry peers rather than viewing relationships solely through the lens of career advancement.
• Maintain momentum through continuous learning. Use the job search period to develop your leadership skills, industry knowledge, and professional presence.
• Embrace vulnerability in new roles. Approaching executive transitions with humility and openness builds credibility and rapport with new teams.
• Persist through challenges and doubts. The path to executive leadership often involves setbacks and frustrations, but persistence remains the ultimate determinant of success.

Your Executive Career Journey

If you’re contemplating an executive career transition, Rowan’s experience illustrates the challenges and rewards of pursuing leadership roles aligned with your values and aspirations. The journey may be longer and more demanding than anticipated, but with clarity, preparation, and persistence, you can achieve your leadership goals.

At Executive Resume Writers, we specialize in supporting accomplished professionals through all stages of executive career transitions. From crafting compelling career narratives to developing the executive presence needed for high-stakes interviews, our services help clients break through career plateaus and achieve their leadership aspirations.

To learn how we can support your executive career journey, visit ExecutiveResumeWriters.com and schedule a consultation. Like Rowan, you may find that this initial conversation becomes the catalyst for transformative career advancement.

Watch the full interview on YouTube.