Strategic Grit:
Navigating a Challenging Executive Job Search in Healthcare
Contents
Contents
Building a Career with Purpose
A case study in resilience, professional branding, and career strategy for executives seeking meaningful transitions.
For Tom O’Donnell, a senior leader with decades of experience in healthcare and higher education, the executive job search wasn’t just about the next step. It was about alignment—aligning his personal values with professional impact. In his words, “I’ve never taken a job for salary. If you can’t grow and make a difference, you’re just kidding yourself.”
Tom’s story is not only about landing a high-level role. It is a case study in leveraging professional branding, strategic thinking, and work ethic during one of the most complex job markets healthcare has seen in years. His path to Vice President of Support Services and Facilities at a regional medical center showcases the importance of readiness, clarity, and grit.
The story unfolds through a conversation with David Kochanek, founder of Executive Resume Writers and a seasoned job search strategist.
Facing a Volatile Healthcare Market
The healthcare industry has always posed unique challenges for job seekers. But for senior leaders, particularly those in operations, support services, or facilities, volatility is a constant. From hiring freezes to geographic limitations, executives must navigate shifting tides with adaptability and foresight.
Tom experienced this firsthand. With nearly 30 years of experience—20 of them in healthcare—he found himself needing to make tough decisions during periods when jobs were scarce. “There was a time I had to take a job 3,000 miles away and come home every three weeks,” he said. “That’s not easy, but I had to set an example for my kids that work ethic matters.”
This level of personal commitment underscores one of Tom’s most defining traits: his unwillingness to sit still, even in challenging circumstances. “Some people told me to just collect unemployment. That’s not in my DNA,” he said. Instead, between consulting roles, Tom worked in the produce department of a grocery store. “I wanted my kids to see me get up and do the work.”
That mindset would prove critical as he prepared for his next professional chapter.
The Strategic Reset: Starting with the Resume
As Tom began evaluating his career options more seriously, he understood the importance of positioning himself effectively in a competitive market. He turned to Executive Resume Writers (ERW) to help him build a powerful personal brand.
“I call it a SWOT (Strengths, Weaknesses, Opportunities, and Threats) analysis,” Tom said. “I scanned a couple of companies to see if there was the right fit. I wanted to work with a firm that really got me. With Executive Resume Writers, I felt like someone was handing off the baton every lap. That was very important to me.”
Together with ERW, Tom rebuilt his resume, refined his messaging, and created a job search strategy tailored to his strengths, geographic preferences, and leadership profile. That preparation positioned him to confidently pursue the types of roles where he could truly make a difference.
From Consultant to Executive Leader
Tom soon joined a regional medical center as a consultant, helping improve operations in support services and facilities. He brought decades of regulatory, organizational, and leadership experience to the role. But what set him apart was his ability to immediately demonstrate value and cultural alignment.
“Two and a half months into the job, the COO and VP of HR started conversations with me about stepping into a VP role,” he explained. “We negotiated back and forth for a couple of weeks, and ultimately, it was a perfect fit.”
This progression wasn’t luck. It was the result of a strategy rooted in visibility and impact. “They saw what I was capable of,” Tom said. “They saw the results and the fit, and that opened the door to something long-term.”
The new role allowed him to lead broad change initiatives, reorganize teams, and focus on employee engagement, one of his personal leadership priorities. “They’ve given me tremendous leeway to make change here,” he added. “They’re focused on work-life balance, and so am I. That’s rare, and it made this the right fit.”
Understanding the Organization’s Pain Points
One of the key reasons Tom was offered the VP position was his ability to address critical gaps. “They were looking for someone with healthcare experience, especially in support services and facilities,” he said. “But more than that, they needed someone with regulatory expertise because they were opening a new hospital.”
Tom’s depth in compliance and his familiarity with large academic medical centers made him an ideal candidate. Beyond technical skills, he brought something else to the table: emotional intelligence and empathy.
“They were very focused on empathy, compassion, and understanding employee engagement,” he shared. “We just hit it out of the park going back and forth with real-life stories from other places I’ve worked. I think that really impressed them.”
Executives today are not only expected to deliver operational results, but they are also expected to connect with teams, develop culture, and lead with integrity. Tom checked every box.
A Grit-Driven Work Ethic That Inspires
Throughout his career, Tom has consistently demonstrated a work ethic rooted in integrity, resilience, and humility. “You want your kids to see you doing the right thing when things are tough,” he said. “You’re giving them a foundation of grit.”
This personal philosophy also informs his leadership style. “As a leader, I think it’s important to be able to talk about your own struggles when your team is going through hard times,” he said. “You have to relate, not just manage.”
That authenticity and willingness to lead by example were key factors in what made Tom successful in the interview process and what continues to define his impact in the workplace.
The Role of Executive Resume Writers
Tom credits ERW not just with resume support, but with helping him build confidence and clarity in his search. “It wasn’t just about the documents,” he said. “It was about having a trusted partner in the process.”
He appreciated the personalized attention and ongoing guidance. “If I had questions or needed edits, the team was there,” he said. “They helped me define the kind of jobs I wanted and where I wanted to be. That focus made all the difference.”
For many executives, the job search process can feel overwhelming or disconnected. ERW helps bridge that gap with services designed to help senior professionals lead their own transition with strategy and strength.
Advice to Fellow Executives
Reflecting on his journey, Tom offers candid advice to executives preparing for a transition:
“Make sure your priorities are clear,” he said. “For me, it was family, opportunity, and growth. Everything else had to fit around that. Don’t just chase titles or salaries. Chase alignment.”
He also emphasizes the importance of patience and perseverance. “You’ll have valleys in your career. That’s okay. What matters is how you respond. Keep moving, keep showing up.”
Key Takeaways for Executive Job Seekers
- Define your values: Knowing what matters most, such as location, impact, and leadership, helps guide smarter decisions.
- Invest in your brand: A well-crafted resume and career narrative can make the difference in a competitive market.
- Show grit: Employers value integrity and resilience, especially in challenging industries like healthcare.
- Find the right partners: Working with a team who understands your goals streamlines the process and increases your confidence.
- Be visible and valuable: Even in temporary or consulting roles, deliver results that get noticed.
- Stay grounded: Career growth is important, but so is personal alignment. Make choices that serve your long-term goals, not just short-term wins.
Tom O’Donnell’s story is a powerful reminder that an executive job search is not just a transaction. It is a transformation. By investing in professional branding, leaning into personal values, and staying grounded through challenging times, Tom carved a path that was both strategic and deeply fulfilling.
For any executive navigating today’s uncertain landscape, Tom’s journey offers a clear blueprint: lead with integrity, prepare with purpose, and surround yourself with partners who help you stay on course.
Listen to Tom’s Full Story
Want to hear the full conversation and get more insight into Tom’s leadership philosophy and career strategy? Watch the full interview on our YouTube Channel.