A reasonable approach to résumé writing
Challenging conventional wisdom for Fortune 500 leaders
For executives navigating an increasingly competitive landscape, the path to an exceptional résumé diverges sharply from conventional advice.
While many award-winning résumé writers focus on power verbs and cutting-edge design, the reality for senior management professionals is far more nuanced and strategic.
This judicious lens—crafted for retained executive search firms like Korn Ferry, Heidrick & Struggles, and Spencer Stuart, and subsequently for C-suites and boards—not only meets the highest standards at the top. It also elevates professionals at every stage of their careers, providing a framework that supports advancement and leadership development across the professional ladder—not just in the C-suite.
I’m Jared Redick, and as a San Francisco-based career coach and executive résumé writer, with 25+ years of experience, I’ve partnered with Fortune 500 executives, board candidates, and rising leaders alike. My approach—shaped by early experience in retained executive search—anchors executive résumés in the factual details that distinguish leaders from their peers, while applying a framework that clarifies career narratives, accelerates professional growth, and positions clients for leadership at every stage of their careers.
The methodology I'll share represents a strategic departure from traditional résumé writing. One that acknowledges the unique realities of executive-level career transitions and the sophisticated audiences who evaluate senior leadership candidates.
Understanding your résumé’s dual audience: humans and machines
The modern executive résumé must navigate an increasingly complex labyrinth where technology has created multiple layers between you and your ultimate decision-makers. Understanding these audiences is crucial for strategic positioning.
Applicant Tracking Systems: Tricky, but Less Critical Than You Think
You've likely heard about Applicant Tracking Systems (ATS)—the automated résumé screening technology used by nearly every major corporation today. Having worked with CTOs who develop ATS solutions, management consultants who recommend them, CHROs who implement them, and even ATS developers themselves, I've discovered something surprising: even these professionals struggle to optimize their own résumés for their systems.
The reality is that numerous firms are developing competing ATS platforms with varying protocols and requirements. While there are general guidelines for content placement, there's no universal agreement among systems. This fragmentation makes comprehensive ATS optimization nearly impossible.
More importantly for executives, according to the U.S. Bureau of Labor Statistics, 70 percent of all jobs are found through networking—a percentage that's even higher for senior management and executive roles. These positions are rarely announced and vetted en masse. Instead, they're frequently filled through networking, word-of-mouth, or handled by executive search firms, meaning your résumé likely won't face the ATS gauntlet.
I use ATS knowledge to guide the résumé design process as a best practice, but I don't recommend that senior management professionals and executives invest heavily in ATS optimization at the expense of more strategic considerations.
Human Readers: Your Primary Audience
Beyond ATS systems, your résumé will be evaluated by several human audiences, each with distinct reading patterns and priorities.
Primary Audiences include retained search and contingency recruiters, in-house recruiters, hiring managers, and those who support them. These professionals see hundreds of résumés daily, developing understandable biases and typically scanning only for specific criteria. They frequently won't read your résumé in detail before an initial interview and may only repurpose sections for dossiers forwarded to decision-making groups.
Secondary Audiences—often overlooked but critically important—include board members, search committee members, senior executives, peer groups, and potential direct reports. Unlike primary audiences, these decision-makers encounter far fewer résumés and are more inclined to read them thoroughly. They make margin notes, craft detailed questions, and yes, they sometimes read cover letters.
This reality addresses the frequently debated question of cover letter relevance. While some argue that cover letters are passé, the evidence at the executive level suggests otherwise: if a cover letter is requested, you can assume it will be read by someone involved in the process. Even if not every reader reviews it, for senior management professionals, the cover letter remains an important tool.
Defining your résumé’s strategic purpose
Opening Microsoft Word and adapting your career story to an attractive template you found online is like forcing your new business strategy into a competitor's framework—the fit will be awkward and the results suboptimal.
Every executive résumé project must begin with strategic clarity about career direction. Too often, we start by looking in the rearview mirror, creating historical biographies rather than forward-focused marketing documents. The key is determining which aspects of your career history will intersect with your architected future direction.
Approaches to strategic clarity:
Comprehensive Career Integration & Exploration: Clients in The Redick Group's Career Integration Program or Career Explorer Program work through my proprietary Job Description Analysis (JDA) tool, developed in 2009. This intensive research and decision-making exercise guides professionals through a discovery process that often resolves strategic questions independently, providing the certainty that informs subsequent résumé development.
Focused Résumé Development: Clients choosing the Résumé Readiness Package provide an annotated job description reflecting their target direction. This approach suits professionals who need "something better, sooner than later" based on existing career clarity, requiring minimal research while ensuring strategic direction guides content decisions.
Both approaches emphasize purpose and intention as the litmus test for every subsequent decision. Your résumé should align with your LinkedIn profile while remaining flexible enough to be tailored for individual opportunities. Unlike LinkedIn's static nature—where a single presence must speak to multiple varied audiences—a well-designed résumé can be strategically customized.
This LinkedIn-résumé alignment presents unique challenges for executives using LinkedIn for business development or exploring career shifts, requiring careful balance between transparency and one’s confidential intentions.
Aligning your résumé and LinkedIn profile presents unique challenges for executives actively leading their organizations while discreetly considering career transitions. Striking the right balance between transparency and protecting confidential intentions is essential at this level.
Crafting strategic résumé content that reflect reality
Once you've defined your executive résumé’s purpose, content decisions become more focused but no less challenging. The difficulty stems from our proximity to our own careers and the temptation during job searches to become suddenly all things to all people—even twenty-five years into a career.
I observe this phenomenon regularly: even externally remarkable careers can feel ordinary to their architects. Professionals with decades of experience instinctively revert to the "pick me!" mentality they used during their first post-college job search.
Embrace niche positioning:
Senior management professionals and executives can’t be all things to all people. Even during career transitions, your compensation reflects expertise, seniority, professional gravitas, and strategic connections—not generalist capabilities.
I've borrowed extensively from niche marketing principles: your background, expertise, and leadership style will be an ideal match for some roles and completely wrong for others. This isn't a limitation. It's a competitive advantage.
A managing director client with a $650,000 base salary once observed, "There are probably only twenty jobs in the U.S. that would match my interests and background, not to mention my wife's career considerations." Rather than viewing this as limiting, he embraced the specificity. He was subsequently recruited for what he describes as "the absolute perfect job on earth" through his LinkedIn profile by a prominent Silicon Valley company, resulting in a career transition featured on Fortune.com.
Senior professionals are rarely sought for what they can be taught—they're valued for what they bring immediately. Career shifts at this level require intention, strategic thinking, and the recognition that you won't fit many roles. The opportunity lies in maximizing your positioning within that rarefied air.
Your résumé content should be keyword-rich without being gimmicky—a fine but crucial distinction that separates strategic positioning from desperate attention-seeking.
Strategic résumé design that supports your message
Résumé design represents the final piece of our strategic framework. While counterintuitive—since design is the first element readers notice—you cannot determine which components your executive résumé should contain or where they should be positioned until you've defined purpose and content.
Balancing standards with flexibility
Most executive résumés include standard elements: a masthead with contact information, a branded executive summary, experience sections with company names, titles, dates, scope, and accomplishments, plus education and sometimes an addendum.
However, significant design flexibility exists beyond these fundamentals. Some résumés benefit from highly creative approaches, while others succeed with traditional formatting. A senior marketer I worked with initially used a clearly written, logically flowing résumé in Arial font with traditional black-and-white formatting. Two months into his search, learning that a target company appreciated creative résumés for creative roles, we developed a colorfully engaging version.
Critical consideration: The creative version included text boxes that would have prevented ATS reading if submitted through traditional channels. However, he had inside intelligence and submitted directly to his contact. The recipients loved the creative approach, demonstrating the importance of understanding your submission route and audience expectations.
Industry and audience considerations
While I admire many award-winning creative résumés from colleagues, they typically wouldn't succeed with the recruiters and hiring entities serving most executives I work with. If your reader—whether board member, search committee participant, retained search recruiter, or hiring manager—can't quickly understand and digest your content, you'll only create frustration.
Hyper-creative résumé design isn't optimal for executives in Fortune 500 companies, and this limitation extends beyond traditionally conservative industries like finance and law. Even recruiters working with technology sector leaders want to quickly and clearly understand what they're reading.
Effective résumé design should be immediately attractive while serving your strategic purpose and making your content easily readable and understandable.
Moving forward strategically
This comprehensive perspective on executive résumé development reflects the sophisticated realities of senior-level career transitions. Unlike conventional résumé advice focused on formatting tricks and keyword density, this approach acknowledges that executive-level positioning requires strategic thinking about audiences, purposes, and the intersection of career planning and market reality.
The most successful executive résumés emerge from this strategic foundation: clear audience understanding, defined purpose aligned with career direction, content that embraces niche positioning rather than broad appeal, and design that supports rather than overshadows your strategic message.
For executives at career crossroads, remember that résumé development can serve as a powerful tool for career coaching, forcing the clarity that benefits not just your résumé, but your entire career transition approach.
About Jared
Jared Redick is a San Francisco-based executive coach, communications strategist, and brand development consultant with more than 25 years of experience helping companies and high-level professionals position themselves for growth and change. Get career coaching here, or co-develop your professional identity here.